Dating After Divorce, Trusting Someone With a Past & Approaching Women IRL (Ep. 68)
About this episode
This episode addresses dating after divorce, trust issues, and how to approach women in real life.
Dating after divorce, trust after infidelity, and how to approach women in real life without being creepy—this episode of Just Ask Her tackles three of the biggest dating questions men are asking right now. Gracie and Tracy respond to real listener submissions about reconnecting with a high school crush after separation, dating someone with a sexual history that feels hard to accept, and figuring out how to gauge a woman’s age respectfully in person. The conversation is honest, practical, and grounded in emotional maturity, self-trust, and intentional dating. If you're a single man trying to date with confidence, navigate modern relationships, and stop overthinking every interaction, this episode will help you slow down, think clearly, and make stronger decisions. Self-Made Man Dating Journal: https://www.amazon.com/dp/B0F9B7M5B3?th=1 Dating Dilemma Submission form: https://forms.gle/e7LTvCkT1fhkFQEF8 Time Stamps / Chapters: 00:00 Opening insight: why people go back to what feels familiar 00:26 Welcome back to Just Ask Her 04:01 Listener 1: Reconnecting with an old high school crush after separation 05:59 Is this real connection or just comfort after a breakup? 09:06 Dating with…
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