Just Ask Her - Dating Advice for Single Men

You’re Not Behind, You’re Learning How to Date


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Dating confidence starts before the date, when you stop performing to be chosen and start showing up as the chooser. In Episode 62 of Just Ask Her, Gracie and certified life coach Tracy respond to three listener submissions on transactional relationships, dating after separation, and building real first-date chemistry.

If you’ve ever felt “behind,” struggled with rejection, or keep hearing “it’s not you, it’s me,” this episode gives you practical mindset shifts and grounded reminders that real connection is built, not bought, and emotional resilience is something you grow through experience.

You’ll also hear how to stop relying on “safe” but stagnant connection, how to handle the grief of dating endings (even early on), and how to create a stronger emotional experience on dates without becoming performative.


In this episode:

  • Why transactional connection can reduce real-world dating initiative

  • The difference between kindness and lack of boundaries

  • A neuroscience-based reframe for why early rejection hurts so much

  • How to build emotional resilience through dating experiences

  • Why first-date “fit” isn’t enough—chemistry is physiological

  • How playful contrast (used sparingly) can create romantic tension

  • The “chooser mindset” exercise that changes your energy on dates

  • The 5-minute pre-date reset to avoid “please choose me” mode

Time Stamps / Chapters

00:00 Pre-date mindset: stop performing, start choosing

00:41 Welcome to Just Ask Her + “dating with confidence” mission

01:00 Minneapolis deep-freeze + “economic ice out” context

04:48 Submission 1 (Ralph): paid companionship/OnlyFans + feeling “behind”

09:11 Why transactional connection blocks real relationships

14:14 Protective narratives, dopamine spikes, and the post-date “crash”

22:05 Practical plan: pause the exclusive online tie + 90-day app commitment

25:01 Submission 2 (Chris): 65, post-separation, rejection grief + resilience

31:02 “You’re grieving the possibility”—why it hurts after 3 in-person dates

37:03 “Is it too late?” + uncertainty is part of dating (not a problem)

39:53 Self-Made Man Dating Journal announcement (Amazon link in show notes)

41:12 Submission 3 (Drew): first dates → “it’s not you, it’s me” texts

46:21 Chemistry = felt experience + playful contrast (don’t overdo it)

55:11 The chooser exercise + 5-minute pre-date reset

01:00:15 Wrap: Episode 62 closing


Hashtags:

#DatingAdvice #DatingConfidence #EmotionalResilience


Keywords:

dating with confidence

chooser mindset dating

stop people pleasing on dates

emotional resilience in dating

handling dating rejection

dating after divorce at 65

dating after separation

grieving the possibility dating

transactional relationships dating

first date chemistry tips

how to get a second date

playful banter on a date

boundaries in dating

mindset before a date


...more
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Just Ask Her - Dating Advice for Single MenBy Hosted by Gracie Pleschourt — Dating Coach + Confidence Expert for Men

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