How Many Drinks on a First Date Is Too Many?

Seeing Other People · Aug 10, 2026 · 45m

Ilana's recording sick, the Syracuse course is officially over and she's not ready to talk about how much she'll miss it, and she saw Hilary Duff sell out MSG and has a lot of feelings. Two listener questions this week: how many drinks on a first date is too many (she ordered a third before he finished his first, and he was expected to pay), and he said after one great date that he doesn't want to rush into anything long term — does that mean he's not looking for a relationship, or should she just ask?

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