Ilana sits down with Allie—an almost 30-year-old who’s never officially had a boyfriend despite years of dating in New York City. Allie opens up about the emotional complexity behind her dating experience, from living with anxiety to navigating body image struggles and self-doubt. They talk about the challenge of watching friends enter relationships while you’re still trying to “meet someone,” the pressure to keep putting yourself out there, and the importance of not judging yourself for where you are.

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