156. The Best First Date Questions + What Daters Regret Not Asking Sooner

Get 90+ questions to ask in early dating

Do you ever struggle with what to talk about on a date? Or maybe you want to get better at building real connections? In this episode, I’m sharing tons of inspiration for great questions to ask in early dating, the worst ones to avoid, and navigating tricky conversations without derailing the date. We’ll also dive into the number one topic that so many daters regret not bringing up sooner, how to answer "why are you single" (and what to ask instead). I also share how to ask better follow-up questions and scripts for handling tough topics like past relationships, STI talks, and career gaps.

Why they don't ask questions and how to deal

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