Ep. 370 Dating After Divorce: The Questions You Need to Ask Before You Get Attached episode artwork

EPISODE · Aug 13, 2026 · 5 MIN

Ep. 370 Dating After Divorce: The Questions You Need to Ask Before You Get Attached

from Dear Divorce Diary: A Fresh Approach To Healing Grief & Building A Life Of Confidence After Divorce · host My Coach Dawn

Dating after divorce is a whole different world.Dating apps. Men holding fish. Men who apparently have never taken a decent selfie. Threesomes. Ethical non-monogamy. And the occasional man who looks way better in person than his profile would have you believe.But underneath all of the chaos is a much more important question:How do you know who you're actually dealing with before you get attached?With Dawn away, Coach Tiffini and Joy are joined again by Christianna, Kelly, and Jo from our current A Different D Word cohort for a very unfiltered conversation about what it actually looks like to start dating after divorce.And this one goes places.We're talking about the questions women often don't ask soon enough:What was your part in your divorce?What does “I want a long-term relationship” actually mean to you?How do I know you've done the work?Are you actually ready for a relationship—or do you just think you are?How do you talk about your ex?What are you looking for five years from now?Are we monogamous?And how early is too early to start asking the really uncomfortable questions?Plus, Jo shares what it's like to date again after nearly 50 years—and why she's asking about everything from STD testing and meeting the family to sexual boundaries, physical health and, yes… whether the pipes still work.But the biggest conversation isn't really about finding the right man.It's about who you are while you're looking for him.Can you state what you want without shrinking it when someone attractive shows up? Can you hold a boundary and watch what he does instead of getting swept up in what he says? Can you walk away when something doesn't fit instead of convincing yourself you can live with it?Because chemistry can make a lot of things feel negotiable that weren't negotiable five minutes before you met him.Before you swipe right—or get attached to the next person who does—this is the conversation we want you to hear.Ask the hard questions. Have a plan. Stick to it. And don't do it alone.Support the showYou can't think your way into healing 🥵 You have to practice your way there 👭If you're ready for the next step, learn more about  A Different D Word and apply here ✨

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Dating after divorce is a whole different world. Dating apps. Men holding fish. Men who apparently have never taken a decent selfie. Threesomes. Ethical non-monogamy. And the occasional man who looks way better in person than his profile would have you believe. But underneath all of the chaos is a much more important question: How do you know who you're actually dealing with before you get attached? With Dawn away, Coach Tiffini and Joy are joined again by Christianna, Kelly, and Jo from our ...

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Ep. 370 Dating After Divorce: The Questions You Need to Ask Before You Get Attached

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This episode was published on August 13, 2026.

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