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Jill Dunn - Matchmaker and The Art of Dating · She’s Smart

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Hey, everybody. Welcome to She's Smart. I'm your host, Maria Robotham.
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On today's episode, we're diving into the world of modern dating with our guest,
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Jill Dunn, the powerhouse behind JillInIt.
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Jill is a professional matchmaker, dating coach, and all-around love guru who
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helps people find real connections in this wild dating landscape.
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She started her journey after navigating the dating world post-divorce and turned
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her experience into a thriving business, matching hundreds of couples along the way.
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From breaking down dating myths to sharing her top tips for finding the one,
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Jill has some seriously good advice.
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So get cozy as we connect, learn, and laugh together on She's Smart.
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Music.
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You have good energy. I feel like everybody is able to just tell me their whole
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life story as soon as we meet and wants to hear mine.
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I totally get that vibe. I'm about to pour all of it out to you.
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Let's talk about everything. I'm so glad that you're here. Thank you for coming
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on. You started your matchmaking service in 2016.
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What preempted that? What got you into doing matchmaking and kind of started that for you?
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So basically, I got that's how it all started. I've always been entrepreneurial,
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but I never in a million years would have thought I would be a matchmaker.
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I don't even think I knew that that was a thing.
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Even when I started, I just got divorced and I was looking for ways to meet
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men. I was on the dating apps.
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There's a very tender place when you are starting dating again after you've
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been married. How long were you married? 10 years.
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Okay. Kids too? Oh yeah. So when I got divorced, my kids were four and six.
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At the time, there was not much time that I didn't have them.
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I wish that I had someone like me when I got divorced.
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To help navigate it, it's a whirlwind. And dating, again, after you've been
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married, for me at least, I had husband expectations for a man that I spent two hours with.
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That's a real lesson. There's so many lessons. And so I thought for sure I would
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get married again right away, maybe have another couple of kids.
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And that was not the course of it.
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And I'm so glad it wasn't because I learned so much.
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And just in that journey is what led me to this work. And it has been the most fulfilling.
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So I started dating on Bumble and all the apps. All the apps.
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Swipe right, swipe left.
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Tender back in the day I was dating. Well, even before I got married,
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I was in my 20s. I just met my ex-husband because we worked together.
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So then in my mid-30s, starting to date, I'm like, how do you date?
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You're living around Fairfield County at that time? Yeah, I was in Norwalk.
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So it's not like you're in the city where there are a ton probably more single people.
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Exactly. And so that was exactly what prompted me to start is because I was
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looking for singles events.
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And the only ones I could find were in the city or Hartford.
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There was nothing. I've got two little kids. I have a background in hosting
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large events like beer festivals and things like that.
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And I'm like, I can definitely host a speed dating event.
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I just sort of said it locally. I'm having a speed dating event at this place
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in this time, and it sold out.
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43 people that first night totally packed the place.
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And I'm like, wow, I'm not the only one that's really searching for authentic
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opportunities to connect.
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So I had another one a couple weeks later. And very naturally from there,
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I was starting to get calls from different restaurants or venues saying,
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hey, why don't you host one of those here?
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So I was doing that all over Fairfield County. And very naturally,
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I started to say, I met this guy at my event in Greenwich that I think would
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really like this woman that I met in Milford.
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Hey, give me your number. I'm going to pass it to him. So that was initially my matchmaking.
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Obviously, now it's totally different. But at the time, that's how it started.
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And then I started to say, all
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right, give me a little bit more information. Do you want to have kids?
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How old are you? What are your plans? This takes a lot of time and a lot of
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heart to do this. There's a lot of thought that goes into it,
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just sitting in it, right?
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So from there, that was maybe a year or two of very casually connecting people.
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Now it is fully evolved where the bulk of the work I do is the matchmaking.
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I continue to do the events as a labor of love and to create opportunities.
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For people to get together in person, because that really is the breakdown of
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modern dating in general.
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I encourage people to come to events, whether they're clients or not,
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help so much to meet people where hundreds of couples have connected at my events
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over the years, but also to connect with other people.
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They've had business partners, best friends, or people have connected and then connected.
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Two women meet at my event, and now one is married to the other one's brother.
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Oh, crazy. Did that happen? Oh, yeah. There's so many connections over time,
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but it gives people practice in dating and getting yourself out there.
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And by the end, people are kissing, people are exchanging numbers,
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people are planning their first date.
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So it really creates a good opportunity for people.
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I love that. When you pick up a client for matchmaking, how does that start?
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Obviously, someone approaches you and they're like, I want to try this.
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What do you start doing with that?
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People find me in a lot of different ways. I don't really do any advertising.
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It's all word of mouth. Isn't that the best? It is. I love that.
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Because then they trust me, which I understand. It's so personal.
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It is. I always take only 15 clients at a time, and I'm on 15 emotional roller
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coasters, or 16 if you count mine.
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Seriously. You're right. It's a lot to take on. And I care about my clients
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so much, and I will only work with people who I feel like I can authentically speak very highly of.
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Okay. Because essentially, I'm your representative.
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I need to be able to say to a woman, you have got to meet this man.
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He's amazing for this, this, and this reason. And he's amazing for you for this,
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this, and this reason. I get to know my clients really well.
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We do either in person or over Zoom intake call, really in depth.
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And from there, I build a profile for them that I'll be able to present either
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to colleagues that I collaborate with or recruiters that I work with or to potential matches.
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And that's where the magic starts brewing. It's really amazing what happens. It's amazing how.
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The difference in a client's life from when we start to when we're done.
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Because almost always, by the
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time we're done, we don't need to continue because they're with someone.
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Oh, wow. Yeah. They're really excited about someone. They're pursuing a relationship.
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How many people have you helped so far?
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Literally hundreds over the years. So I know it's a beautiful thing and I feel
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super honored to be a part of it.
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And that's why I don't regret any part of my own journey.
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I really feel like I was chosen to do this.
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And I feel really honored to be a part of this special and tender part of people's
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lives. I don't take it lightly.
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I ride the wave with my clients for sure.
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I feel like regrets are just passe. Because what are you going to regret?
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There was something that was meant to be and happened.
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I think when I was younger, I regretted stuff because I didn't know.
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But as we get older, you hit that over 40 age and you're like, fuck it.
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Everything was supposed to happen this way. I'm supposed to be here right now.
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I think it takes some time to get to that place where you're like,
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this happened and there was a reason for it.
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What made you create the program just for women?
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What is the four day flip? The four day flip is everything that I learned the hard way.
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It tends to be women who are navigating dating after divorce that gravitate to the program.
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It's really inexpensive and completely self-guided. So you do it on your own time.
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You can do it in a week and be in a completely different place by next weekend.
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It's four ways in four days to completely transform your dating life.
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It is packed with everything that I've learned through my own lessons as a single
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woman navigating dating,
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but also through working with hundreds of other women, a compilation of all
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of the good juicy bits that you need.
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It really is transformative in just four
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days my promise with the four-day flip is that you'll
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have no more bad dates by that I
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mean no more bad dates is what can
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you make of that experience what did you pick up what did you put down there's
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no wasted dates there's no wasted space or time as long as you can reflect and
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see what it was about that even led you to agree with the date with that man to begin with.
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Yeah. So what are some mistakes that women are making?
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Dating is so much more complicated now than it used to be. A huge part of that
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is because there's too much information that
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People in general, but we're talking about women right here.
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Women tend to have a certain set of checkboxes, you know, height, income, hair.
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I don't date a man with a goatee. I only date men who wear sunscreen.
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Like, I have. Wait, is that really seriously one of them? Actually heard it
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all. Yes. Yes. This is not a deal breaker.
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We're looking to connect with someone on core values. Yeah.
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Do you enjoy your time together? Do they make you laugh? Do they make you feel
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sexy? Do they make you feel attractive, appealing?
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How do you feel in their company? That is a huge problem that women are sabotaging their own dating lives,
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just passing on men who are 5'11 instead of six feet. It makes me insane.
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Another huge problem, and this is both men and women make, dating somebody based
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on the outcome. If you're on a first date with someone, you should be thinking
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about, how does this feel right now?
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Do I want to hang out with them again?
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Makes sense. Not attached to a certain outcome.
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He mentioned that he might want to live in Atlanta at some point.
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I never want to live in Atlanta, so this is never going to work.
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We're just one day at a time, one step at a time.
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So dating not attached to the outcome, but really just staying in each date.
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I always tell clients, the only goal of a first date is to find out if you want a second one.
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Yeah. It should not be an interview on either side. It literally is a vibe check. Date one, vibe check.
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That's it. Do I want to hang out with them again? And so by just simplifying
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it like that, it just takes the pressure off.
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And if you can just get out of your head like that and just see,
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this is how you probably dated your husband, right?
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You met your husband and you're like, oh yeah i liked him i'll hang out
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with him again and we were best we were we dated then
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he broke up with me and then big mistake
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big mistake but it all came back in the end it's okay worked out
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then we became best friends i love it we best friends and then it all just kind
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of happened yeah we met through friends so back in the day this was 2005 that's
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how long i've known so back Like in 2005, there were the apps,
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but the majority of us were meeting people that were friends of friends.
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I have friends who met each other in college and they got married.
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I have friends that met studying abroad.
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It must be a very different world out there where everyone is on apps.
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How has it changed the dating world?
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The apps, they're an opportunity.
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And as long as the person that's swiping can keep that mentality of it,
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that this is just one other opportunity to meet people, it essentially is meeting
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someone in a bar. Thank you.
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You don't know them. You just see their face. It should just be that.
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Hi. Hi. Okay. Do you want to go out? I think you're attractive.
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Yeah. Let's go out and vibe check.
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Okay. Yeah. But now it's become the only way.
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And this instant gratification, like, nope, nope, nope. What the hell do you
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know about someone in a second?
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Nothing. I actually just saw this guy the other day that is one of my favorite
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men I ever matched with on the app.
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This is back when Bumble, you could shake it if you think you made a mistake
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and you want to go back to that guy.
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So I came across this guy and he had a big, long beard with icicles in it. I was like, not for me.
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And I was with a friend, was like, wait, wait, he's cute. So I shook it and I got him back.
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And then I looked at his other pictures. I was like, oh my gosh,
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he's so handsome, beautiful, charming eyes. we matched and went out on probably
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a dozen dates over the course of two years.
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We were in totally different places in our lives, but we really liked each other.
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We weren't right for each other long term.
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But I always think about him, Mike G, because I didn't know anything about him
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from his icy beard picture. What's going on? Why are you icy beard?
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I just assumed it was a no for me, but he taught me so much and was so tender.
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I really enjoyed my time with him because there There are no bad dates. There are no bad dates.
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I always think about my grandparents who are like my love story that I always
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long for. They met when they were teenagers.
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She wasn't concerned with his height or his income. They met,
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enjoyed each other, and committed to a life together without distraction.
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They loved each other, had a beautiful life, and a wonderful family.
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They both just passed away two years ago. At the same time? Grandma passed,
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and then Grandpa basically said, just so you guys know, I'm out.
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And we were like, wait, but no, you're not even sick. He's like,
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what am I going to do here without her?
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And five weeks later, he was gone and we had their memorials together.
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Do I have a broken heart? You literally do. Some people are like,
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what am I going to do without him?
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I always think about them because we're just wasting opportunities to connect
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with good people because we're too focused on checkboxes.
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Another piece of dating right now, especially after divorce,
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which is a whole, it's a different thing.
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Yeah when people are single and they're meeting in their 20s or even early 30s
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you're connecting and then you're deciding who you're going to be together.
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Building a life together. Whereas dating in your mid 30s or 40s or 50s or 60s,
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I have a client who's 86 widowed twice and she is not going.
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God bless her. She's out. She's out a man.
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God bless her. She's like, Jill, I'm wearing my angel pins and I know you're
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going to find them. I love her. She's the best.
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She's got a FaceTime date tonight. She had lunch with someone else last weekend.
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She is not messing around. I love her. She's like, I'm not going out.
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Why do we need to? Why? we can just keep going. Exactly.
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So like dating after you already are who you are is a totally different space
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because people have to be open
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to accepting that someone else is not going to come in and fit already.
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Both parties have to be a little bit malleable in order to meld together.
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But the truth is, if you find somebody that's right for you, you will.
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And they will. So that's why I say on a first date, stop thinking about,
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well, this can't possibly work because his kids are five years older than mine.
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See if you like hanging out and the rest will figure itself out.
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Because you're like a whole person. You might have kids. You might have a career.
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You might be doing a million different things. You're not building it.
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It's built. You're a whole person already. There's a way that you keep your home.
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There's a way that you keep your car. There's things that you choose to spend money on.
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I know for me, once I got divorced, I was like, I'm going to buy whatever I want.
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I'm going to get those shoes. I'm going to get whatever I want.
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And there's no one to keep track of me.
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It's my money. It's my time. It's my...
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Bag. There's, you know, different things that you have to change when you're
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in a partnership, when you're sharing money, when you're sharing a household,
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when you're raising kids together.
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Both parties have to be a little bit flexible, but not right away.
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Be yourselves first and just be open to bending a little. Yeah. For the right person.
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I wanted to develop a way where I can work with people more in a group.
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So that's what the Love Club is. The Love Club, we have members only monthly events online.
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So there's different roundtable topics each month. Like this month for February,
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the topic will be creating chemistry in a new connection.
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I share some information at the beginning and then Love Club members chime in.
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It's a good balance of men and women. So it's nice to get input from everybody.
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And then there's live Q&A at the end. So it's like free dating advice.
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It's for singles who are serious about getting serious.
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There's a lot of different perks to the Love Club. One of the main perks is
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that, so I have a free database for singles.
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So there's thousands of singles in Connecticut and New York in my database.
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It's one of the places I go to look for potential matches for my private clients.
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If I have a new client, I'll look in my database and Love Club members are the
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ones that I screen first for potential clients.
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So that is a huge perk.
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So it's a no-brainer and it's totally affordable.
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It's just my way of sort of trying to be able to work with a group rather than
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one-on-one. How many people are in it?
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60. I record the Love Club monthly member calls and some people watch the replay.
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Sometimes there's five people on a call and sometimes 40.
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It just depends. If you're serious about getting serious and you want to get
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in the love club, you're not hopefully going to be single the whole year.
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We're going to be looking for a relationship for you.
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Even people who are newly in relationships come on for the live dating advice to help navigate.
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It's really helpful for people. Do you ever work with people outside of Connecticut?
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Yeah. Connecticut, New York. I had a client in Florida that I met when I was
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in Florida, and he was like, I want to work with you.
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I'm part of a matchmakers alliance where I collaborate with 200 matchmakers
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all over the country, all over the world, really.
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And I've been able to connect my clients with other singles like in Australia and England.
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It's unbelievable what can happen.
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I have someone in my mind for you. Yes. Send them my way.
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You never know. Just making a connection. I always say people come across my
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desk for a reason at the right time.
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Okay. So what are the rules to start having sex with someone?
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Was it like three dates? This is so tricky. Four dates.
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Like, does it matter now? When you're young, I don't know. When you're young,
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at least for me, I wasn't giving away the goods right away. Right.
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That was just how I did things. Others were different. But when you're older
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and you've had children, you've been in relationships, you've been married,
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what is it now? It's tricky.
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I think it really is a case-by-case thing that slow and steady wins the race.
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And I think as we get older, it's more important to wait until fourth, fifth, sixth date.
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I have a colleague that recommends 12. She has a 12-date rule, Matchmaker Maria.
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And I see why. But also, I see why maybe you don't want to spend so much time
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investing if you're not going to be compatible.
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If the intimacy is not going to be compatible. Right. But there are other ways
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to be connected without actually having sex.
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I think waiting until you're exclusive is ideal because otherwise it just stirs
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everything up and your vision is blurred and you're thinking, oh, this guy is great.
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But like, is he or did you just stop paying attention? Yeah. The sex is just awesome.
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Because the sex was good. Yeah. And that's what I'm here for,
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right? Exactly. And then you forget that's not what you came for.
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Exactly. It was for something longer term. Totally.
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So sometimes it's better to just pump it back. All right. So do you hear that, ladies?
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Just wait. Just try to wait. Give yourself some time getting to know the person
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before you jump into it. I think it just is better.
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Is there a client in particular that had this checklist that you got through
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to her that she broke through it and ended up with someone with maybe things on the checklist?
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Yeah. Like the goatee? Right. Oh, yeah. No sunscreen? No sunscreen.
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I mean, that was too much. Almost always...
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When there is a couple that I connect, one or both of them initially decline
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the introduction, saying they're not my type.
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Really? Almost always. And it usually is one or both will say,
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okay, fine, I'll trust you because nothing else is working.
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Then they totally hit it off and they're like, you were right.
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I'm like, I know. I'm pretty good at this. My job.
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I can see it even if you can't because you are relying on this checklist that is worthless.
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I have a broader scope on things.
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So I can see that your lifestyles, your core values,
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your plans for marriage and family, the big things, your sense of humor,
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like I can see you fit together in ways that you can't because you are focused
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on these unimportant details.
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It really happens almost every time. And I hate to say I told you so, but I almost do say it.
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Do you ever suggest to clients that they get new photos taken? Almost every client.
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I have a photographer that I work with that shoots almost every client.
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Sometimes clients come to me with photos that are appropriate,
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but a lot of times they just have selfies.
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I want to make the most of our time together.
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So I have a lifestyle photographer that comes, we'll go to your home,
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get pictures of you laughing, walking, doing what you enjoy.
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And it just makes a huge difference.
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Brings the personality of who that person is out more than the photo you took
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at Disneyland with your kids five years ago.
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Yeah. Recent pictures. Yes. In flattering clothing, in flattering lighting.
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Yeah. Especially men, not great at taking pictures of themselves.
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That's another tip that I tell women all the time. You can't just swipe no on
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them because they're not good at taking pictures.
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They're just taking it like this and then throwing it up. Or they all think
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they have to take their shirt off. I know. Please stop. I don't.
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It's just not necessary.
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If you're buff, we'll notice. Exactly. If you've got great arms, we'll see it.
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Don't put it all out there. Leave something to the imagination.
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There's appetizers for a reason.
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It helps me represent them in the most flattering light.
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A lot of times when people come to me, they're already worn down from trying to date on their own.
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Having someone manage it for them is such a relief that they can just rest into
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the process, enjoy. I always say the volume is on my end.
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I'm doing all the screening. Like before my client has met anyone,
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I've already had a FaceTime call with them, run a background check, verify their identity.
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I make sure that this person is who they say they are and have spoken to them
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either once, sometimes multiple times, just to make sure we're on the mark.
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They do not speak before the first date, which is a huge asset because you meet on a dating app.
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There's so many opportunities for people to mess that up before they even make
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it to a first date. I arrange the date, time and a place.
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Everybody knows what to expect. It's kind of like a blind date.
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Except you already know that everything important aligns. You've seen pictures.
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You know who you're meeting.
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And, you know, it works. Matchmaking is important.
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Probably the most organic way that you can meet someone now.
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People were going out in bars and meeting, right?
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Now people are in a bar, they're on their phone. They're basically in do not disturb.
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Men also feel less comfortable approaching women.
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Women feel less comfortable with men approaching them.
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So it's really dating apps.
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Even there's so many things that have happened historically over the last 15
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years that have just alienated people and made them a little bit more homebody,
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a little bit more protected.
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Even coming out of COVID, people are like, wait, why are you getting so close
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to me? I'm not in my bubble.
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Even though the bubbles are over, there's still a piece of that that makes people feel unsafe.
24:21
And so that's where I come in because I help scoop people up and put them safely together.
24:28
Do you do device free for your events? For the events?
24:32
Yeah. And I tell people for speed dating events, mixers and one-on-one dates, no bad dates.
24:38
Even if you're not sitting across from your husband right now,
24:41
you have another human being's undivided attention for five minutes.
24:46
There is so much value in that, especially given what we've all gone through
24:49
over the last five years.
24:51
Like you get to talk to a human being. Lucky you.
24:54
Enjoy it. I couldn't imagine sitting at a date and having someone like staring
24:58
at their phone the whole time. Oh, it does happen.
25:00
Oh my gosh. I think about that now with these stupid phones.
25:04
And even the young kids when they're dating, what does that even look like?
25:09
Like when you get into high school and half the time you've been on your phone
25:13
for the last three years.
25:14
Have you even looked up to see who's around? Yeah. My son started middle school in 2021.
25:22
They were at desks six feet apart where you can't talk unless your mask is up.
25:27
They lost a few years of that longing to connect with people and to be close
25:34
because they're told to stay away.
25:36
He's in 10th grade now and he cares much more about golf and money than he does
25:41
about girls. He's way too busy.
25:43
And that's just his personality. But I think in general, there are not as many
25:47
kids going to the high school dances and stuff like that.
25:51
They're just less connected in that way. What's that going to do for them when
25:55
they get older? Well, there's less babies being made, less people getting married.
25:58
And people prioritizing, especially women, prioritizing their career,
26:02
making sure that they can, because the advice that your mom gave you looks a
26:06
lot different now. To have your own money now, I mean, that takes into your 40s.
26:11
And so there's so many women that I work with that come to me with frozen eggs,
26:17
with an established career, and they're like, okay, I'm ready. Let's do it now.
26:23
I'm like, all right, let's do it. The freezing of the eggs. Lots of friends who did that.
26:27
There's a lot of women that have gotten themselves set and are prepared to go
26:33
it alone and have their baby on their own.
26:36
A lot of women do and I think it's incredible.
26:39
The strength in doing that. I know, amazing.
26:42
And then after they'll come around and say, okay, I got my babies, I'm ready to date. Yeah.
26:47
So there are a lot of soft spots along the way that people need to be aware
26:53
and understanding of in each other's lives.
26:55
That goes back to what I said about when you're meeting people to date,
26:59
to consider a life with, and you're already an adult, you have to be soft.
27:05
You have to be malleable. You have to be understanding and accept that this
27:10
person is not going to have the same life that you do. If somebody came to you
27:14
that was 35 or 40 years old and had no baggage and no life experience,
27:18
I think that would be weird.
27:20
Questionable? Yes, questionable. Whereas if they already, they're like,
27:23
all right, look, I got this ex-husband thing. I went through this. I traveled.
27:27
I did these things. I got some eggs frozen. And I'm ready for this, this, and this.
27:31
All right. They actually had life. Experiences, connections, broken hearts.
27:36
It's all part of it. What are some of the challenges from traditional dating,
27:40
like how we used to do it, and dating now, modern dating?
27:45
I think major challenge and in a very basic way is that men still have the basic
27:54
instinct to pursue and provide.
27:57
A lot of women are like, don't get that door from me.
28:02
I can take care of my part of the bill. Not all. I personally still like when
28:07
a man gets my door and gets my chair and picks up my bill, but not all women do.
28:12
So that alone is the shift because men are confused and a confused buyer doesn't buy.
28:21
A man who's confused, like, I don't know, should I get the door?
28:23
Should I pick up the tab? I don't want to offend her, but I want to be masculine.
28:28
They're like, never mind. That is the basic breakdown, in my opinion,
28:33
of modern dating and relationships.
28:37
Yeah. If a man didn't open the door for me, if my boys don't open the door for
28:41
people, these are certain things that I believe they should be doing.
28:45
I agree. Because I grew up like that. My husband's grew up like that.
28:48
My son gets the door. That is fascinating.
28:51
It's a huge problem. We hear about this masculinity and the breakdown of masculinity
28:53
and how they're not allowed to be masculine.
28:55
But now on the flip side, we've got all this trad wife stuff happening where
28:59
traditional wives are coming back or they're staying home.
29:01
They want to cook from scratch and they're doing all these things.
29:04
So I'm wondering if we're going to start shifting it. Yeah.
29:06
I think that being a feminist is owning every part of femininity.
29:11
I'm going to be sexy. I'm going to be funny.
29:13
I'm going to be professional. I'm going to be badass. I'm going to walk in the door.
29:17
I'm going to wear every outfit and piece of jewel that I want to wear. And I'm going to own it.
29:20
I'm also going to let my husband open the door for me. I want him to open the
29:25
door for me. I want him to take the garbage out and do things.
29:28
Sure, I can do it. But guess what? I have a choice.
29:31
I don't have to do it. So I'm not going to do it.
29:35
I find that we can be a feminist without losing our femininity.
29:39
I don't want to be a man. I really like being a woman. Me too.
29:42
And I finally liked being a woman. It took a long time to be comfortable in
29:46
that and be like, no, I'm going to do all the things and feel really good and feminine.
29:52
That I feel like is the biggest power we can have.
29:55
I think that is one of the biggest lessons that I share with female clients.
30:01
The people who hire me are successful and established.
30:07
One of the biggest lessons I learned in dating, right, I'm on my own.
30:11
My kids have a dad. So I'm a single mom. But they have a dad.
30:14
Yes. I'm running my home, running my kids' lives, running my life, running a business.
30:19
I'm in control, in control, in control. And so when I was dating,
30:23
my instinct was to be in control.
30:27
And guess what a controlling woman does?
30:30
Repels masculine men. They don't know what to do. They turn into liquid and go away.
30:36
It is a man repellent. And I was definitely attracting masculine men,
30:43
but I was running them out of town.
30:46
When I first started dating again, like to really, I did, I've done so much
30:51
work on myself and on my past and my relationship with my father.
30:55
And so I've really done it. I realized getting into a place where you can be
31:00
feminine and allow a man to be masculine, but still take care of your shit. Mm hmm.
31:09
That's it. To know when to turn it off.
31:13
And a lot of that comes in practice. Bite my tongue.
31:17
I'm like, OK, I can't like you said, I can do this, but I don't have to. Yes.
31:24
And even in dating, there's little, it seems insignificant and can seem to some
31:31
people like some women may not want to like dumb themselves down to ask for
31:35
help and things that they can surely do themselves.
31:37
But just a little exercise I challenge women to do is ask for help with something.
31:44
There was a client having trouble with her and she was dating a man who is a
31:49
tech genius. I said, why don't you ask him?
31:51
Well, no, because I can just hire someone. I'll just get the geek squad to come.
31:54
And I was like, let him help you.
31:57
He wants to help you. It will bring you closer.
31:59
If he feels like he serves a purpose for you, it doesn't have to be him killing
32:05
a deer and dragging it in to feed you.
32:07
But it does the same thing for him to help you solve your computer problem. Yeah. Just ask for help.
32:14
Do you have a really memorable story from your matchmaking?
32:19
Last night, I had a memorable experience with my client, Joy,
32:23
who's 86, the one I told you about. Love Joy. I love Joy.
32:27
Joy's going to come on the podcast. We should get Joy on the podcast.
32:31
Oh, she would tear it up. Joy is the absolute best.
32:34
I call Joy and she's like, hang on, Jill, let me turn down the music. I'm dancing around.
32:39
Or she's on her way to Zumba or she's on her way to the golf club.
32:43
Joy does not mess around. I want to know everything that happened to Joy in her six years.
32:47
I know. I love her. I collaborate with other matchmakers and we have these monthly
32:51
meetings where we're sharing certain clients that we're really looking for someone for, right?
32:57
So I shared joy recently and a colleague in Ohio sent me a message two days
33:06
ago and said I actually have an 88 year old man who's in Ohio who's a pilot who has a plane.
33:12
Who is open to relocation and I don't know what do you think I'm like let's
33:17
do it let's connect them so I tell joy you got to meet this guy and she's like
33:21
all right let's do it she calls me last night.
33:23
She's like, Jill, I'm overjoyed. You wouldn't believe how many things we have
33:28
in common. She has family in Ohio.
33:31
They both were born in Florida. They were both in Danbury, Connecticut at the
33:35
same time. They both golf.
33:37
They have all these same interests. And she's like, I think you did it.
33:40
I think you found the one. And then meanwhile, I get a text message from my
33:44
colleague with a screenshot from him that says, I think you did it.
33:48
I think you found the And so then my colleague and I, Amanda,
33:53
are texting each other like, yeah, we did it.
33:55
Oh, that's magic. Joy is all of us. I mean, seriously, she's like,
34:01
I want someone to hold me.
34:04
Oh, I want someone to hold me. Yes. And that's what everybody wants.
34:08
So it's like literally if I have one message to everyone who's dating, it's just soften.
34:15
Like, let your guard down. Stop quizzing each other.
34:18
Be yourself and be joy. Just be joy.
34:22
Just be joy. God, I love her. I know, me too. I want her to have an Instagram.
34:25
I want to follow it. I want to know what they're doing. Where are they flying?
34:28
Oh, we're going to. What are their adventures?
34:30
I know. Literally, the adventures of joy in the pilot. Like, let's make it happen.
34:35
I want to see the whole thing. What's something, as someone's working with you
34:38
as a matchmaker, that might surprise people?
34:41
I think one thing is that people think, I don't have the time to work with a
34:45
matchmaker. The truth is that you don't have to do anything.
34:49
This actually entirely takes this off your plate.
34:52
You just get to show up for a date with a highly qualified, perfect for you
34:57
candidate once or twice a month.
35:00
I do the time consuming part.
35:02
I have the volume. I do the screening. I make sure they're right for you.
35:06
And you just get to show up for a couple hours and see if you want to see them again.
35:10
Hopefully have a good time. Can you share one tip for our dating listeners that
35:15
could help them in their dating mindset or their approach?
35:19
I would say the top tip is just to date, not attached to the outcome. Top tip.
35:25
Just go have some fun. Even if the people that have the hardest time with this
35:30
are the people who read my younger clients who are 35-year-old women who are
35:37
really intentionally looking for husband, father for their children.
35:41
So there is a bit of a timeline for them. So they're feeling like it has to be interviewee.
35:48
But especially them, drop it.
35:52
Not attached to the outcome. First date, vibe check. Always.
35:56
And also, the expectation between first date, second date, a big piece is like,
36:05
everybody has different communication styles, right?
36:07
So I think communicating about the type of communication is...
36:13
You're comfortable with is key. For a man to say to a woman,
36:17
I had a really nice time with you.
36:19
I'd love to see you again. How about next weekend?
36:22
And she says, sure, I would love that. And for him to say, great,
36:26
I'll check in with you on Thursday to finalize the details.
36:29
I'm not going to text you every day. So now you don't have to be anxious about
36:33
that all week. I'm going to text you on Thursday.
36:36
Communicate about how you're going to communicate. And the woman can do the
36:40
same thing. Like I had a really nice time at dinner last night.
36:43
Just so you know, I definitely want to see you again. I'm not a big texter during
36:48
the week, but how about we touch base on Thursday to see what we're going to do?
36:53
Just to clarify, you know, so many people are so anxious and,
37:00
you know, I've definitely been there too.
37:01
Two hours later, he's going to text me. Maybe he changed his mind.
37:05
Oh my God, did I have something in my teeth? What did I say? Is my phone working?
37:08
Can someone text me and tell me if my phone is working? Exactly.
37:11
Why isn't he texting me? Well, because you're strangers.
37:15
You don't need to get to know each other over text. I was having this conversation
37:19
with a client last night who was really anxious about, had two great dates with a man.
37:24
His last words to her were, really looking forward to seeing you again.
37:28
I'll get in touch to plan the next date.
37:31
Two days later, she hadn't heard from him. And she's like, I can't imagine what
37:34
went wrong. Everything is the same.
37:36
Yes. Nothing has changed for him. Go out with your girlfriends.
37:41
Sign up for tennis. Stay busy. Date other men.
37:45
Date multiple people at the same time. Until there is a conversation about exclusivity,
37:50
which in my opinion should be initiated by the man.
37:53
You should be dating as many people as you want to, as many people as your schedule allows for.
37:58
Not sleeping with everybody because, again, we're waiting for that until we're in a relationship.
38:02
But don't put all your eggs in his basket. You don't even know him yet.
38:07
Just keep it flowing. And naturally, the one who's right for you will be the
38:12
one that you want to see on a Saturday night over the other ones.
38:16
Why should the man initiate it?
38:19
Again, that goes back to that old-fashioned feminine masculine polarity in a relationship.
38:25
That's not right for everyone. And some women, especially if they're very anxious,
38:30
will implode if they do not share with their potential man.
38:37
What they want, which is fine too. Communicating about how you want to communicate is key.
38:43
And for her to say to him, I've really been enjoying getting to know you these
38:47
last four or five weeks and I want to be honest with you.
38:50
I'm seeing other people, but you're my favorite.
38:53
That's a nice, easy, breezy way of saying it. It's not like,
38:56
I want to be with you forever. Right.
38:58
Like, it's not so aggressive. I think my claws are like, I've got a lot of things
39:02
going on, but you're my favorite. It's actually a very nice thing to say.
39:05
Yeah. It opens and lets him say something back.
39:08
Okay. So at the end of every episode, I ask three questions.
39:11
What have you changed your mind about recently?
39:13
Okay. So forever, for almost my entire adult life, I poured a glass of wine.
39:20
I wasn't getting drunk, but it was a ritual.
39:23
Every night I poured a glass of wine when my kids were babies,
39:26
when my kids were bigger, when I was alone, when I wasn't alone.
39:29
I wasn't getting drunk. I was always in control, but I always did that, right?
39:34
Last January, I had one too many out with my girlfriend one night and I felt horrible the next day.
39:40
And I'm like, I am changing my mind about this.
39:44
This does not feel to me anymore.
39:48
I wasn't doing it very often, but once every couple of months,
39:51
I'd be groggy the next day. I was like, I'm working too hard in the gym.
39:55
I have too many things that I love and care about to have one too many ever.
40:00
Initially, I just stopped drinking at home. I'll still have wine or cocktails,
40:04
margaritas. I love a drink sometimes.
40:06
My new ritual, which I adapted maybe halfway into last year,
40:10
I've changed my mind about wine as a ritual to these delicious CBD THC drinks. Stop.
40:17
You are the second person to come on and talk about these drinks.
40:22
I love them. You can get them at some liquor stores. 99 Bottles sells them.
40:27
I wait until all my stuff's done.
40:29
And you don't get high. You don't get anything. You just...
40:33
Turn down a notch and it's delicious. I have my little nugget ice maker and
40:37
I put in a wine glass and I sip it like a cocktail, but there's no alcohol.
40:43
They just give you like a little click of chill and a little click of like,
40:49
I've done all I can do today. The rest can wait until the morning.
40:54
Beautiful, deep sleep. What brand do you drink? They're called Can.
40:58
And actually, I don't know if they're made in Westport, but Dave Briggs is one
41:03
of the investors and he's in Westport.
41:04
Yeah. So it's like supporting local. And they sell them at 99 Bottles in Westport.
41:09
Highly recommend them. And they're delicious.
41:12
What is the most random thing on your bucket list? The most random thing on
41:17
my bucket list is to learn West Coast swing.
41:20
Oh, yes. Have you seen those videos? We took swing classes in New York. I think I need to do that.
41:26
Yeah. So fun. They look so fun. I'm like, Like, I want to...
41:29
There's got to be studios out here.
41:31
Yes, for sure. I just have to prioritize it. I love that dance.
41:34
It's so freeing. I love to dance. It's just the way they feel their feet and swing and dip.
41:38
Yeah, that's awesome. What is one
41:40
piece of advice that you would give your younger self? You are not fat.
41:45
Right? Hell yeah. Oh, my God. How much time did I waste thinking I was fat when I was not fat?
41:52
I wish there was some ways of pre-program young people to appreciate their body
42:02
at different ages and stages.
42:04
That has definitely been an evolution for me. I've always had a different body than my girlfriends.
42:12
I've always been curvy. Now I
42:15
love my curves and I really embrace my small waist, wide hips and big ass.
42:21
It's me. It's like my signature.
42:23
I didn't always like it. And also, I think a piece of that is I didn't always
42:28
know how to dress appropriately.
42:32
To flatter my figure. So I was trying to squeeze into the same stuff that my girlfriends were.
42:37
All of that comes with age experience and coming into yourself.
42:41
If I could just sink that in there when I was 110 pounds and 17.
42:47
That poor girl. There's so much there because, and maybe it comes with age,
42:53
with being comfortable in your own body.
42:54
It also comes with accepting who you are and what is yours.
43:00
The tiny waist, the badonk. Look, I don't think I've ever was proud of my badonk.
43:05
I am four foot nothing and never knew how to dress because there's nothing for me.
43:09
So I think I became a stylist because I had to teach myself how to dress.
43:15
Now I can dress anyone because I can figure out how to put this thing together.
43:19
I can take care of everyone else. It also takes a lot of work. It does. I have two boys.
43:24
So I don't deal with their body images the way that the girls do.
43:28
At least they don't have it.
43:29
They're very confident, those two. Yeah, yeah. Thank God.
43:32
But I see these girls and they're all the most beautiful human beings, all of my little nieces.
43:38
And I think of how I talked to myself at that age and how awful it was and how mean I was to myself.
43:44
And I never in a million years would ever look at any of them and be that mean
43:48
because they're all so incredibly beautiful in every way.
43:53
And we weren't taught how to be kind to ourselves like that.
43:57
I grew up with, God love you, mommy.
44:01
But I grew up with a mom who was doing lean cuisines and drinking tab and snack
44:06
wells and God knows every other 80s and 90s fad that you could possibly think of.
44:13
And we just didn't have that around us to be like, no, you're fucking queen
44:17
and you're good yeah every part of you is good embrace the way now i do though
44:22
i saw this yeah me too i have a 13 year old daughter.
44:25
It is a practice in my house. And my kids both know I have a personal trainer.
44:29
I really prioritize my health and wellness.
44:31
And I never talk about it being about being skinny.
44:36
It is always about being strong and healthy. When I compliment my daughter,
44:41
she is beautiful inside and out.
44:44
But this is always about being healthy, strong, about longevity.
44:49
And my son, I always say he's going to be the best husband ever because he just is so that guy.
44:57
He appreciates, he compliments my daughter's sense of humor.
45:01
He's going to be the best husband ever, you know. And because of that,
45:05
my daughter, she's going to have very high expectations.
45:08
I am so glad you came on. Thank you for being on here. Me too.
45:11
I'm going to put your website down below. Everyone can see it and they can reach out if they want to.
45:15
I'm going to be sending this to all my single friends out there.
45:17
Please, you never know. You know who you are. You know who I'm thinking about
45:20
right now. Yeah. That's awesome.
45:25
Thank you so much for joining me today on She's Smart. New episodes drop every Thursday.
45:30
Don't forget to subscribe and share. Stay cozy.