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Have you ever walked away from a date wondering if you should give it another shot or just move on? In this episode, I’m breaking down a simple three-part framework to help you decide whether to keep seeing someone in those crucial first few dates. I’ll share the exact questions I asked myself back when I was dating, including the ones that helped me recognize when it was worth going on a second (or even tenth) date, and when it was time to let go. I’ll also tell you why enjoying yourself matters more than “feeling the spark,” how to spot dealbreakers early, and why it’s okay to live in the uncertainty of not knowing yet. At the end, I answer a dating dilemma about how to bring up the subject of divorce and an ex when you’re a few months into something new.

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261 episodes