Old-School Dating: I Tried Courting Like My Grandma for 24 Hours

This Escalated Quickly · Jul 1, 2026 · 5m

Liv decides to spend a day dating exactly like her grandma would: handwritten note instead of a text, bringing flowers, actually asking about family, and the wildly anachronistic idea of a 'chaperone' (her sober friend on standby). This monologue walks listeners through the pre-date prep, the hilariously awkward moments when modern expectations collide with old-school manners, and the petty triumphs—like getting a compliment without decoding an emoji. Along the way Liv confesses the tiny rules she secretly misses, dishes a hot take on why some vintage moves still work, and tells the chaotic…