195. Second Date or Move On? How to Decide Who To Keep Seeing

195. Second Date or Move On? How to Decide Who To Keep Seeing

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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Episoder(262)

232. Are You Staying for the Right Reasons? (Dating Dilemmas)

232. Are You Staying for the Right Reasons? (Dating Dilemmas)

I'm answering four real dating dilemmas from listeners stuck on whether to stay or leave a relationship. I get into how to end a medium-term relationship, what to do when you've been on the fence for ...

27 Jan 34min

231. What We Get Wrong About Avoidant Attachment w/ Travis Ambrose

231. What We Get Wrong About Avoidant Attachment w/ Travis Ambrose

I'm chatting with Travis Ambrose, an attachment-focused coach who specializes in helping people on the avoidant end of the spectrum heal and build healthier relationships. We're discussing everything ...

23 Jan 48min

230. Your First Date Pep Talk + Flirting Tips

230. Your First Date Pep Talk + Flirting Tips

Let's get ready for a first date! I'm sharing a pep talk for your next first date, plus my best quick tips for flirting, so you can actually create a romantic connection instead of just a friendly one...

20 Jan 28min

229. The 4 Things You Should Know by the 4th Date w/ Amy Nobile Messing

229. The 4 Things You Should Know by the 4th Date w/ Amy Nobile Messing

I'm chatting with Amy Nobile Messing, a holistic dating coach who "turbo dated" her way through NYC after leaving a 20-year marriage in her 40. She's now remarried and helping clients of all ages find...

16 Jan 52min

228. Signs They’re Ready for a Relationship

228. Signs They’re Ready for a Relationship

I’m breaking down the real signs someone is actually ready for a relationship beyond what they say on a dating app or how excited they seem early on. I’m also covering what doesn’t mean much on its ow...

13 Jan 27min

227. Dating When You've Never Been In A Relationship w/ Allora Dannon

227. Dating When You've Never Been In A Relationship w/ Allora Dannon

In this episode, I'm chatting with Allora Dannon, who went on her first date ever at 32. She's now engaged, and we're discussing everything from how to bring up your lack of experience on a date to na...

9 Jan 54min

226. 8 "Red Flags" That Are Normal in Long-Term Relationships

226. 8 "Red Flags" That Are Normal in Long-Term Relationships

In this episode, I'm breaking down 8 things that seem like red flags but are actually just part of being with someone for a while, like feeling bored sometimes, not being "in love" every single day, h...

6 Jan 35min

225. How To Date NATO (Not Attached To Outcome) w/ Erika Ettin

225. How To Date NATO (Not Attached To Outcome) w/ Erika Ettin

In this episode, I’m joined by dating coach Erika Ettin again to break down the mindset shifts that make dating feel calmer, clearer, and more intentional. We talk about dating NATO (not attached to o...

2 Jan 49min

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