121. Signs it's time to break up (and how to end it)

121. Signs it's time to break up (and how to end it)

Knowing when to end a relationship is tricky, especially if there’s no glaring dealbreaker—sometimes, it’s just not the right fit. How do you know when it’s time to move on?

In this episode, I’m breaking down how to decide whether to keep dating someone or walk away, whether you’re just a few dates in or have been in a relationship for years. I’ll share tips for recognizing signs that it’s over, how to decide with compassion and practical advice for breaking things off based on where you are in your dating journey. I also share my personal experience and exact scripts to start the break up conversation.


Get 15% off at Jenni Kayne with promo code DATING15 - https://www.jennikayne.com/


Episodes mentioned:

  • Ep 93: Why you need momentum in early dating (and how to create it)


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Episoder(261)

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

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

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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

224. Top 10 Tips For Dating Intentionally In 2026

224. Top 10 Tips For Dating Intentionally In 2026

Starting fresh in dating can feel exciting and overwhelming at the same time. In this episode, I'm sharing my top 10 tips for dating intentionally in 2026, from building confidence and resilience to u...

30 Des 202539min

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