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

If you’re stuck in mixed signals, waiting to be “reconsidered,” or navigating a relationship where marriage and long-term goals don’t match, this episode breaks down what to do next,without chasing, arguing, or negotiating your needs away.

In Episode 61 of Just Ask Her, the hosts respond to three submissions: a confusing “pheromones” rejection, an 8-year relationship where ambition and lifestyle expectations diverged, and a 14-year partnership where one person wants marriage and closeness while theother doesn’t.

This is for anyone who wants clarity, stronger boundaries, and a reality-based way to decide whether to stay, especially when love is present but alignment isn’t.

Time Stamps:  

00:00 — If nothing changes: the question you have to answer

00:31 — Episode 61 begins + submission from Steven

01:03 — “Pheromones didn’t agree”: rejection + confusion

02:39 — Why people rarely give the real reason

04:44 — “I’m not interested” is the only sentence you need

06:10 — Attraction isn’t a debate + closure is self-made

09:13 — Submission from Jay: 8-year relationship + proposal plans

12:18 — Living like roommates: provider mindset vs connection

15:20 — Love vs misalignment: wanting to co-create a life

20:12 — Resentment, pressure, and the breakup dynamics

22:08 — Stop pausing your life; release the fantasy future

23:13 — Self-Made Man Dating Journal promo (Amazon)

24:32 — Submission from Paul: 14 years together, no marriage

26:18 — Facts vs story: loneliness + competing for attention

30:07 — Is there a compromise that both people choose?

Keywords:

mixed signals after rejection

she said not interested

pheromones dating excuse

attraction is not a debate

closure after breakup

relationship misalignment goals

love isn’t enough relationship

one partner wants marriage

she doesn’t want to get married

loneliness in a relationship

long term relationship advice

resentment kills intimacy

how to stop waiting for an ex

dating boundaries for men

self trust in relationships

Hashtags:  

#relationshipadvice

#datingadvice

#relationships

#boundaries

#selftrust

Episode 60: Should You Take Her Back? Plus Confessing Feelings to Your Best Friend

Welcome back! After a brief hiatus to upgrade our studio setup, Gracie and Tracy are back with real talk on navigating tricky dating situations.

In This Episode:

Question 1: Should I Give Her Another Chance?Rick shares his story about a woman who ghosted him after two months of dating, only to reach out months later with an apology. Should he take her back? We discuss:

• How to separate facts from fear-based interpretations
• The difference between compassion and accommodating bad behavior
• What to watch for if you decide to give someone a second chance
• Why confidence comes from trusting yourself in uncertainty, not predicting outcomes

Question 2: How Do I Tell My Best Friend I Have Feelings?Dan writes in about having romantic feelings for his lifelong best friend (who also happens to be his boss's daughter). We cover:

• Why the real fear isn't "weirding her out"—it's facing potential rejection
• How 68% of relationships actually start as friendships
• The difference between a dramatic "confession" and a mature conversation
• How to handle the situation professionally regardless of the outcome

Question 3: Why Should Men Listen to Women's Dating Advice?An anonymous listener challenges why women should give dating advice to men. We address:

• The difference between facts and the stories our brains tell us
• How contempt and defensiveness make you undateable
• Why expertise comes from observing what creates results, not gender
• The importance of filtering the information you consume online

Key Takeaways:

• You're not here to be chosen—you're the chooser
• Confidence is earned by doing hard things and surviving any outcome
• The risk isn't rejection; it's self-abandonment
• Your job is to become a man you trust, then learn to choose well

Resources Mentioned:

• The Self-Made Man Dating Journal - available on Amazon

Connect With Us:

• Rate us on Spotify or Apple Podcasts
• Share this episode with friends who need to hear it

Next Episode: More real dating questions, more honest answers. See you next week!

Chemistry and availability aren’t the same thing—and that’s a key reason dating can feel confusing. In this episode of Just Ask Her, Gracie and her mom/co-host (certified life coach) Tracy answer three real submissions about mixed signals at work, dating after a layoff, and why first dates from apps often get canceled last-minute.

If you’re dating with intention and you keep wondering “What did I do wrong?”, this episode helps you separate the facts from the story your brain is trying to write—so you can move forward with more confidence and less overthinking.

You’ll hear practical scripts and mindset shifts for navigating modern dating dynamics (especially on the apps), plus how to protect your time and self-respect while still staying open to connection.

In this episode:

• Why “chemistry” doesn’t equal “availability” (and how faith/values can change outcomes)

• Friendly vs. flirty in work settings—and how to get clarity without spiraling

• Should you mention unemployment on your dating profile? (Spoiler: no)

• How to talk about a recent layoff on a first date with confidence

• Why app dates get canceled so often—and how not to take it personally

• The better response when someone cancels (so you don’t carry the whole reschedule)

• Why comparison is wrecking your confidence (and what to do instead)

  
  

  
  

Time Stamps / Chapters:

00:00 — Welcome to 2026 + new studio setup

00:02:21 — Submission #1: Mixed signals at work + mini golf invite “180”

00:05:56 — Friendly vs. flirty: how to get clarity (especially at work)

00:10:42 — Faith/values + “two truths can coexist”

00:13:02 — Lesson: you can do everything right and still not control outcomes

00:15:44 — Submission #2: Laid off—how it affects dating + your profile

00:19:06 — Why you shouldn’t disclose unemployment on apps (and what to say instead)

00:24:11 — Mind drama, shame, overexplaining: what actually hurts your dating life

00:28:49 — Submission #3: Dates keep canceling + confidence crash from comparison

00:32:05 — App reality: most matches don’t meet + lots of day-of cancellations

00:37:49 — What to text when she cancels (and why “pick a new time” backfires)

00:45:00 — Stop over-texting before the date: save conversation for in-person

00:47:32 — Episode wrap: Episode 59 + what’s next

Keywords:

chemistry vs availability dating

friendly vs flirty at work

mixed signals workplace crush

how to ask her out clearly

dating after being laid off

unemployed and dating advice

should I mention unemployment dating profile

what to say when she cancels date

dating app dates cancelled last minute

why dating apps ghosting happens

stop over texting before first date

confidence after rejection dating

dating apps decision fatigue

how to reschedule a date text

modern dating advice for men

Hashtags:

#DatingAdvice #OnlineDating #Confidence

Are you ready to take control of your dating life and attract the women you want? In Episode 58 of the "Just Ask Her" podcast, dating expert Gracie Pleschourt and certified life coach Tracy Pleschourt celebrate a year of growth, share their impressive Spotify Wrapped stats, and answer real listener questions about dating challenges, mindset shifts, and self-confidence.

In this episode:

• The Just Ask Her podcast’s first full year recap and top Spotify Wrapped achievements (Top 5% of videos, most shared show, and more!)
• Meet Noodle, the adorable new dachshund puppy joining the show
• Listener submissions: Navigating dating with neurodivergence, overcoming “bad luck” in relationships, and embracing singlehood with confidence
• Mindset advice for men who feel stuck or defeated in dating
• The importance of self-awareness, communication, and taking the lead in your dating journey
• Announcing the launch of the Self-Made Man Dating Journal—designed to help single men track, reflect, and improve their dating experiences
• Exciting updates for 2026, including a new production team and upgraded video setup

Whether you’re struggling with dating setbacks, wondering how to be the “chooser” in your love life, or just want to hear real, no-nonsense advice from women who get it, this episode is packed with actionable tips and inspiration.

Resources mentioned:

• Self-Made Man Dating Journal on Amazon
• Follow Gracie on Instagram and TikTok: @datingwithgracie

Don’t forget to rate, review, and share the show on Spotify or Apple Podcasts to help more listeners find us!

Feeling alone this Christmas Eve? You’re not the only one. In this special holiday episode of Just Ask Her, dating expert Gracie Pleschourt and certified life coach Tracy Pleschourt get real about why so many men find themselves single during the holidays—and what you can do to make sure next year is different.

We’re not here as coaches or experts, but as your family—your older or younger sister, your mom—ready to tell you the truth you need to hear. We’ll talk about the real reasons you’re stuck in your dating life, the stories you tell yourself that keep you from moving forward, and the steps you can take to break the cycle of loneliness.

Key topics include:

• Why comparing yourself to others on social media is sabotaging your happiness
• The truth about texting your ex (and why it never helps)
• How to get unstuck and start attracting the relationship you want
• The three steps to change: Decide, Get Clarity, and Do the Work
• Practical advice for building confidence, meeting new people, and becoming someone you’re proud of
• A 90-day challenge to transform your dating life

You’re not broken, and you’re not alone. Tune in for honest, no-BS advice, encouragement, and a promise: next Christmas can be different—if you decide to do the work.

Subscribe for weekly episodes with actionable tips, real talk, and the support you need to change your dating life for good.

Merry Christmas from Gracie, & Tracy

Welcome back to Just Ask Her, the no-nonsense dating advice podcast for men who want real answers from a woman’s perspective! In Episode 56, dating expert Gracie Pleschourt and certified life coach Tracy Pleschourt tackle your toughest dating dilemmas, from decoding mixed signals to making the most of first dates.

In this episode:

• How to tell if she’s interested or just being friendly
• The power of direct communication: Why “just ask her” is the best strategy
• Navigating texting habits, physical touch, and gift-giving in modern dating
• Coping with rejection and building confidence after loss
• Real listener submissions: Rekindled friendships, workplace crushes, and moving on after heartbreak
• The best first date ideas for online matches and in-person connections
• Are singles events and speed dating worth it? Pros, cons, and creative alternatives
• Special announcement: The Self-Made Man Dating Journal is now available on Amazon—track your progress and level up your dating life!

Plus: Rapid-fire Q&A, reality TV talk, and why being the chooser (not just the chosen) is the key to dating success.

Resources & Links:

• Grab your copy of the Self-Made Man Dating Journal on Amazon
• Follow Gracie on Instagram and TikTok: @datingwithgracie

If you enjoyed this episode, please rate us on Spotify or Apple Podcasts and share with your friends. Your support helps more men find real, actionable dating advice!

Tune in next week for a special holiday episode!

Show Notes

Episode 55: Why She Didn’t Text Back: Real Talk on Dating Apps, Instagram DMs, and Moving On

Welcome back to Just Ask Her—the no-nonsense dating advice podcast for men, hosted by dating expert Gracie Pleschourt and certified life coach Tracy Pleschourt. In this episode, Gracie and Tracy tackle three listener submissions that highlight the most common struggles men face in modern dating: ghosting, mixed signals, and the frustration of online dating.

In this episode:

• Submission 1: A listener wonders if an ex’s Instagram like means she wants to reconnect, and Gracie and Tracy break down why social media signals are rarely what they seem—and how to move forward with confidence.
• Submission 2: Tyler asks why women don’t respond to his Instagram DMs, despite his best efforts and a strong profile. The hosts explain the hidden variables of online messaging, why your worth isn’t tied to replies, and the “Rule of 100” for building dating resilience.
• Submission 3: Dan shares his story of heartbreak after divorce and struggles to find connection on dating apps. Gracie and Tracy offer advice on reframing rejection, increasing your “reps” in dating, and why your past doesn’t define your future.

Plus:

• The launch of the Self-Made Man Dating Journal—designed to help single men track their dating progress, reflect, and grow.
• Why mindset is the most important factor in dating success.
• How to separate facts from stories when facing rejection.
• The importance of volume and persistence in online dating.

Key Takeaways:

• Don’t read too much into social media interactions—focus on real communication and alignment.
• Your value isn’t determined by how many replies you get; it’s about choosing yourself first.
• Dating is a numbers game—get more reps before drawing conclusions.
• Healing from heartbreak is a journey, and every experience is a step toward the right relationship.

Resources Mentioned:

• Self-Made Man Dating Journal on Amazon
• Follow Gracie on Instagram and TikTok: @datingwithgracie

If you enjoyed this episode, please rate us on Spotify or Apple Podcasts and share with your friends! New episodes every Wednesday.

Should You Approach Her When She's Alone? Ghosting, Rejection & Building Real Confidence (Ep. 54)

Show Notes:

Listener submissions spark honest conversations about:

• The right (and wrong) ways to approach women in different contexts
• How to handle mixed signals and trust your instincts after being hurt
• Why ghosting and rejection don’t define your worth
• The hidden pitfalls of dating apps and how to reframe “rejection”
• Building confidence and self-awareness for better connections

Plus, Gracie and Tracy share personal stories, Thanksgiving chaos, and announce the launch of the Self-Made Man Dating Journal—designed to help you track, reflect, and level up your dating life.

Don’t miss the practical advice, mindset shifts, and real talk that will help you date with more confidence and clarity.

Listener questions featured from: James, Kyle, Jake, and Miguel.

Resources mentioned:

• Self-Made Man Dating Journal (available now on Amazon
• Follow Gracie on Instagram & TikTok: @datingwithgracie

New episodes every Wednesday!

You’ll learn:

• When (and how) to approach women respectfully—alone or in groups
• Why ghosting and rejection aren’t reflections of your worth
• How to trust your instincts and set healthy boundaries
• The truth about dating apps and self-sabotaging beliefs
• Actionable tips for self-awareness and authentic connection

Plus, hear about the new Self-Made Man Dating Journal, designed to help you track your progress and break old patterns.

Tune in for honest advice, relatable stories, and the mindset shifts you need to succeed in modern dating.

Subscribe for new episodes every Wednesday, and follow Gracie on Instagram & TikTok @datingwithgracie.

Grab your copy of the Self-Made Man Dating Journal on Amazon

Episode Description:

Gratitude, Growth, and Real Talk: Navigating Dating Challenges & Self-Trust

In this special Thanksgiving and birthday episode, Gracie and Tracy reflect on the power of gratitude, embracing new chapters, and the lessons learned at 25.

They answer listener questions about moving on after betrayal, dating after divorce, and how to handle fast-paced connections in the digital age. Plus, they introduce the Self-Made Man Dating Journal—designed to help you track your progress and date with intention.Feeling stuck in your dating life or struggling to move on after heartbreak?

In this episode, Gracie and Tracy get real about gratitude, personal growth, and the messy realities of modern dating. They answer listener questions about letting go of toxic relationships, dating after divorce, and how to communicate your needs and boundaries.

Whether you're navigating new connections or healing from the past, you'll find practical advice and encouragement to help you trust yourself and date with intention.

Plus, discover the new Self-Made Man Dating Journal—your guide to tracking progress and building better relationships.

Listen now for a dose of honesty, hope, and inspiration!