In this episode, Gracie and Tracy tackle three powerful listener submissions about dating challenges, online reputation, and moving on after heartbreak. They offer no-nonsense advice on handling public shaming in online groups, building momentum with a newly single neighbor, and recovering from a whirlwind romance that ended abruptly. Plus, they announce the launch of the Self-Made Man Dating Journal, designed to help men reflect and grow in their dating lives.
Show Notes:
00:00 – Introduction
02:00 – Listener Submission #1: Anthony’s Story
25:00 – Announcement: Self-Made Man Dating Journal
28:00 – Listener Submission #2: Alex’s Story
40:00 – Listener Submission #3: Jake’s Story
Self-Made Man Dating Journal Self-Made Man: Dating Journal for Men | Track Confidence, Patterns & Reflections | Build Self-Mastery, Emotional Intelligence & Intentional Dating Habits | Personal Growth Journal
Get Gracie’s Free Guides at: 👉https://datingwithgracie.com/
Check out the Dating With Gracie Community at: 👉https://www.skool.com/dating/about
Want to be featured on the podcast? Submit your story & question: 👉 "Just Ask Her" Podcast Submission
Follow for more honest, no-fluff dating advice: 📲 Instagram | TikTok | YouTube
Hosts:
Gracie Pleschourt (Dating Expert) & Tracy Pleschourt (Certified Life Coach)
Episode Summary:
In this episode, Gracie and Tracy tackle real listener questions about dating challenges, mindset shifts, and taking control of your love life. They offer no-nonsense advice from a woman’s perspective, helping single men date with confidence and intention.
Listener Submissions & Key Takeaways:
Dakota’s Dilemma:
A 31-year-old entrepreneur struggling to find quality matches while living with family and rebuilding financially.
Advice:
Don’t wait passively for love—be open and intentional about meeting new people.
Own your journey and talk about your growth with confidence.
Geography matters on dating apps, but don’t let location limit your options—explore new ways to meet women.
Your ambition and integrity are attractive; focus on sharing who you’re becoming.
Kyle’s Missed Connection:
A 32-year-old crane operator wonders if he missed out on a romantic opportunity after a church encounter fizzled.
Advice:
You did nothing wrong—sometimes timing just isn’t right.
Don’t dwell on “what could have been.” Stay open to new opportunities in places you enjoy.
Contentment is great, but combine it with curiosity and intention to avoid stagnation.
Emotional readiness is key to relationship success.
George’s Unrequited Interest:
A 34-year-old man questions whether to keep talking to a woman who isn’t ready to date.
Advice:
When someone says they’re not interested or ready, believe them.
Set boundaries and move on to free your energy for the right relationship.
Don’t confuse hope with reality—choose clarity and self-respect.
Special Segment:
Product Launch: The Self-Made Man Dating Journal is now available on Amazon! Designed for single men to track dates, reflect, and build self-awareness for better dating outcomes. Limited first run—grab yours before they’re gone!
Calls to Action:
Rate and review the podcast on Spotify or Apple Podcasts to help others find the show.
Share this episode with friends who could use real, actionable dating advice.
Follow Gracie on Instagram and TikTok: @datingwithgracie
New Episodes:
Tune in every Wednesday morning for fresh, honest dating advice—no matter where you are or what your situation is, just ask her!
Self-Made Man Dating Journal Self-Made Man: Dating Journal for Men | Track Confidence, Patterns & Reflections | Build Self-Mastery, Emotional Intelligence & Intentional Dating Habits | Personal Growth Journal
Get Gracie’s Free Guides at: 👉https://datingwithgracie.com/
Check out the Dating With Gracie Community at: 👉https://www.skool.com/dating/about
Want to be featured on the podcast? Submit your story & question: 👉 "Just Ask Her" Podcast Submission
Follow for more honest, no-fluff dating advice: 📲 Instagram | TikTok | YouTube
In this powerful episode, we hear from three men navigating dating after heartbreak, rejection, and personal transformation. Tiago, a newly single dad, opens up about falling hard for a woman fresh out of her own divorce—and the grief of not being chosen. Brady asks how to confidently start conversations in person and online. And Brandon vulnerably explores a repeating pattern of giving too much and being left behind.
If you’ve ever asked yourself: Why does love feel so one-sided? or Am I stuck in the same cycle?—this one is for you. We offer honest answers, emotional insight, and real strategies to move forward without closing your heart.
💬 Topics we cover:
Rebound heartbreak and emotional availability
How to start conversations that actually connect
The over-functioning pattern that leaves good men feeling unseen
Building confidence without performing
When to try again—and when to walk away for good
Whether you're fresh out of a relationship or ready to rewrite your love story, you'll walk away with tools, validation, and hope.
Submission 1: Tiago (00:00)
After a 14-year marriage, Tiago dives into dating again—only to fall for a woman not yet over her own divorce. We explore why emotionally available men often feel heartbreak more deeply, and how to stop trying to prove your worth to someone who isn’t ready to choose you back.
Submission 2: Brady (21:45)
Brady asks a common question: How do I start the conversation—on apps or in person—without being awkward or overthinking it? We break down what actually matters in first impressions (hint: it’s not cleverness), and how curiosity beats performance every time.
Submission 3: Brandon (38:10)
Brandon is done chasing women who don’t choose him back. We unpack the anxious attachment pattern of over-giving, why it keeps showing up, and how to lead with discernment instead of devotion in future relationships.
Self-Made Man Dating Journal Self-Made Man: Dating Journal for Men | Track Confidence, Patterns & Reflections | Build Self-Mastery, Emotional Intelligence & Intentional Dating Habits | Personal Growth Journal
Get Gracie’s Free Guides at: 👉https://datingwithgracie.com/
Check out the Dating With Gracie Community at: 👉https://www.skool.com/dating/about
Want to be featured on the podcast? Submit your story & question: 👉 "Just Ask Her" Podcast Submission
Follow for more honest, no-fluff dating advice: 📲 Instagram | TikTok | YouTube
If you found this episode helpful, please rate us on Spotify or Apple Podcasts and share it with a friend. New episodes every Wednesday!
DatingAdvice #SingleMen #DatingApps #Heartbreak #Confidence #JustAskHerPodcast
It’s one of the most painful dating experiences: everything feels amazing… and then she disappears.
In this raw, relatable episode of Just Ask Her, we unpack three powerful submissions from men navigating ghosting, rejection, and confusion after what felt like real connection:
Luke opens up about an overseas trip that changed everything with a woman he thought he was building something real with. Now she’s gone—no warning, no clarity—and he’s still holding on.
Spencer shares the story of his whirlwind 4-date romance with a woman who seemed all-in—until she ghosted him after planning two more dates. What gives?
Conor bravely tells us what it’s like being 30, never having been in a relationship, and constantly getting close—only to be shut out. He asks: What am I doing wrong, and how do I keep going?
💬 Gracie and Tracy go deep in this one, breaking down what ghosting really means, why it often has nothing to do with you, and what women are thinking when they pull away after connection. We also explore:
What to do when you still have feelings but she cuts contact
The truth about mixed signals and sudden disappearances
Why “perfect dates” don’t always lead to commitment
How to rebuild your confidence after being ghosted
When (and how) to reach out again—or let go completely
Whether you’ve been left on read or still playing back every moment of your last date, this episode will give you clarity, closure, and hope.
Self-Made Man Dating Journal: https://www.amazon.com/dp/B0F9B7M5B3?th=1
Get Gracie’s Free Guides at: 👉https://datingwithgracie.com/
Check out the Dating With Gracie Community at: 👉https://www.skool.com/dating/about
Want to be featured on the podcast? Submit your story & question: 👉 "Just Ask Her" Podcast Submission
Follow for more honest, no-fluff dating advice: 📲 Instagram | TikTok | YouTube
She said she only wanted something casual… but your heart didn’t get the memo.
In this episode of Just Ask Her, we’re diving into three real stories that hit home for a lot of men:
A 36-year-old man rekindles something with the woman who once ghosted him—only to find himself falling all over again. Is she just bored… or is there still a chance?
Another listener goes from intimate and honest connection to total silence after dating a single mom—what happened, and how do you respond to ghosting that makes no sense?
Plus, we talk about first-date anxiety with a guy who knows he’s a catch… but struggles to show it early on.
If you’ve ever questioned whether you’re being patient or just played, this episode will give you honest advice, a woman’s perspective, and the clarity you need to stop spinning in circles.
Get the Self-Made Man Dating Journal: 👉https://www.amazon.com/dp/B0F9B7SQBY?th=1
Get Gracie’s Free Guides at: 👉https://datingwithgracie.com/
Check out the Dating With Gracie Community at: 👉https://www.skool.com/dating/about
Want to be featured on the podcast? Submit your story & question: 👉 https://forms.gle/naT2MHcb5vPjU6K68
Get Gracie’s Free Guides at: 👉https://datingwithgracie.com/
Check out the Dating With Gracie Community at: 👉https://www.skool.com/dating/about
Want to be featured on the podcast? Submit your story & question: 👉 https://forms.gle/naT2MHcb5vPjU6K68
This week on Just Ask Her, we’re tackling three very real (and wildly different) dating dilemmas from our listeners:
Carlos wants to know if there’s any hope for a conservative guy dating in a liberal city—or if he should hold out for a future move.
Mark has rekindled things with his high school sweetheart… but there’s one big problem: she’s still best friends with his ex-wife.
And an anonymous bachelor is wondering how to strike up a conversation with the woman he always runs into—but never has a chance to talk to.
We’re talking dating across political lines, what to do when the past gets in the way of the present, and how to approach a girl you barely know without being weird about it. Let’s dive in.
Get Your Self-Made Man Dating Journal: https://www.amazon.com/dp/B0F9B7SQBY?th=1
Get on The Dating Differently Academy Waitlist at: https://datingwithgracie.com/dda-waitlist-4055
Get Gracie’s Free Guides at: 👉https://datingwithgracie.com/
Check out the Dating With Gracie Community at: 👉https://www.skool.com/dating/about
Want to be featured on the podcast? Submit your story & question: 👉 "Just Ask Her" Podcast Submission
Follow for more honest, no-fluff dating advice: 📲 Instagram | TikTok | YouTube
In today’s episode, we’re diving into three powerful stories from men navigating the messy middle of modern dating:
💔 Luke thought he was one step away from proposing—until she blindsided him with a breakup.
😓 Josh is tired of being the one who always initiates, and he’s starting to feel the desperation creeping in.
🥲 Jerome had the best first date of his life… but now she’s gone quiet, and he’s left wondering if he should reach out again.
We’ll talk about what to do when effort feels one-sided, why some women emotionally check out long before they leave, and how to find clarity when the door hasn’t fully closed.
If you’ve ever felt blindsided, confused, or stuck on “what could’ve been,” this episode is for you.
Get Gracie’s Free Guides at: 👉https://datingwithgracie.com/
Check out the Dating With Gracie Community at: 👉https://www.skool.com/dating/about
Want to be featured on the podcast? Submit your story & question: 👉 "Just Ask Her" Podcast Submission
Follow for more honest, no-fluff dating advice: 📲 Instagram | TikTok | YouTube
In Episode 31 of Just Ask Her, we dive into one of the most confusing dating experiences: when everything starts fast, feels promising… and then suddenly falls apart. From whirlwind reconnections to mixed signals after first dates, these listener stories are full of emotional highs, unexpected letdowns, and hard-earned lessons.
Evan shares what it’s like to be pulled in deeply—then pushed away after one perfect weekend. AL wonders if he blew his chance with a hostess who seemed interested… until she wasn’t. And Kyle opens up about how one experience erased months of confidence he built after leaving the dating apps behind.
We explore how to spot premature intensity, how to protect your heart without closing it off, and why confidence has to come from within—not from how someone responds to you. Whether you’ve been ghosted after a great weekend or left wondering what went wrong, this one’s for you.
Sign Up For the FREE Attraction Masterclass: https://datingwithgracie.com/masterclass
Get Gracie’s Free Guides at: 👉https://datingwithgracie.com/
Check out the Dating With Gracie Community at: 👉https://www.skool.com/dating/about
Want to be featured on the podcast? Submit your story & question: 👉 "Just Ask Her" Podcast Submission
Follow for more honest, no-fluff dating advice: 📲 Instagram | TikTok | YouTube
What does it really take to start over in dating—whether you’re 36, 62, or healing from deep emotional loss? In this episode of Just Ask Her, we respond to three powerful submissions from men navigating dating later in life.
We talk about:
How to date after a bipolar diagnosis and little-to-no experience
The challenges of dating in your 60s and getting past the first date
Whether it’s fair to pursue someone who’s still grieving
Why your dating history matters less than your emotional readiness
How to show emotional maturity without coming on too strong
If you’ve ever felt behind, stuck, or uncertain about how to move forward in your love life—this episode is your sign to begin again.
Save Your Seat At The Attraction Masterclass: https://datingwithgracie.com/masterclass
Get Gracie’s Free Guides at: 👉https://datingwithgracie.com/
Want to be featured on the podcast? Submit your story & question: 👉 "Just Ask Her" Podcast Submission
Follow for more honest, no-fluff dating advice: 📲 Instagram | TikTok | YouTube
Why do some of your best dates go absolutely nowhere? In Episode 29 of Just Ask Her, Gracie and Tracy break down the most frustrating moments in modern dating—from ghosting after great chemistry to navigating the mixed signals that leave you stuck in limbo.
We answer three listener questions that highlight common (but painful) scenarios:
Why women disappear after everything seems to be going well
How to read and respond to mixed signals from someone who says they want something casual but keeps acting romantic
What to do when you're trying to build a connection with a woman at work without landing in the friend zone
Whether you're dating after divorce, struggling to get past the second date, or wondering how to stand out without coming on too strong, this episode is packed with honest advice and fresh insights from two women who’ve seen it all.
💬 Topics covered:
Why great dates don’t always turn into relationships
Emotional chemistry vs. timing compatibility
Slow burns, fast fades, and everything in between
The “safe guy” trap and how to avoid it
Building romantic tension without pressure
Signs it’s time to walk away vs. keep showing up
Get Gracie’s Free Guides at: 👉https://datingwithgracie.com/
Check out the Dating With Gracie Community at: 👉https://www.skool.com/dating/about
Want to be featured on the podcast? Submit your story & question: 👉 "Just Ask Her" Podcast Submission
Follow for more honest, no-fluff dating advice: 📲 Instagram | TikTok | YouTube
In this episode of 'Just Ask Her,' hosts Gracie Pleschourt, a dating expert, and her co-host Tracy Pleschourt, a certified life coach, tackle three insightful submissions from male listeners facing distinct dating challenges. They begin with JJ, a college student wondering how to keep a new spark alive over a three-month summer break. Next, they advise Mike, a 30-year-old trauma survivor worried if his career focus and limited social life are unattractive to potential partners. Finally, they address Rich, who is confused by a mixed response from a woman he reached out to on social media. Throughout, Gracie and Tracy offer practical advice and emphasize the importance of emotional availability, intentional communication, and self-worth in dating.
00:00 Introduction and Podcast Overview
00:53 Listener Submission: Keeping the Spark Alive Over Summer
02:34 Advice for Maintaining Long-Distance Connections
09:59 Personal Stories and Reflections on College Dating
14:40 Listener Submission: Balancing Career and Social Life
17:44 Understanding Different Relationship Expectations
18:56 Balancing Career and Social Life
19:51 Leveraging Social Skills for Dating
21:01 Utilizing Online Resources for Dating
21:49 Embracing Your Achievements with Confidence
23:23 Podcast Outro and Listener Engagement
23:42 Analyzing a Listener's Dating Dilemma
24:40 Decoding Mixed Signals in Dating
26:33 The Importance of Clear Communication
28:16 Managing Rejection and Building Resilience
32:37 Encouragement and Final Thoughts
Get Gracie’s Free Guides at: 👉https://datingwithgracie.com/
Check out the Dating With Gracie Community at: 👉https://www.skool.com/dating/about
Want to be featured on the podcast? Submit your story & question: 👉 "Just Ask Her" Podcast Submission
Follow for more honest, no-fluff dating advice: 📲 Instagram | TikTok | YouTube
In this episode of Just Ask Her, Gracie and Tracy tackle three powerful submissions from men feeling stuck—whether it’s bumping into your ex at the gym, navigating emotionally messy flings in big-city bars, or wondering if your small town is what’s keeping you single.
You'll hear:
How to protect your peace when “no contact” isn’t possible
Why big city dating often feels like one big performance
Whether moving for love is a smart idea—or a sneaky form of self-abandonment
What to do when your dating apps feel like a loop of dead ends
And how to build real momentum when everything feels stuck—romantically, socially, even sexually
This is a grounded, honest episode about self-respect, emotional clarity, and trusting your own inner compass. Because sometimes the real work isn’t in chasing love—it’s in clearing space for it.
Get Gracie’s Free Guides at: 👉https://datingwithgracie.com/
Check out the Dating With Gracie Community at: 👉https://www.skool.com/dating/about
Want to be featured on the podcast? Submit your story & question: 👉 https://forms.gle/naT2MHcb5vPjU6K68
Follow for more honest, no-fluff dating advice: 📲 Instagram | TikTok | YouTube
EP 26 — Timing, Betrayal, and the Friend Zone: Real Advice for Modern Dating
In this episode of Just Ask Her, Gracie and Tracy tackle three brutally honest listener submissions from men navigating complex, emotional dating challenges:
🩺 A cancer survivor steps into the dating world for the first time—only to kiss a woman who turns out to be married.
🧸 A self-described “safe guy” keeps getting friend-zoned and wants to know how to be seen as a romantic option.
🚩 A man reconnects with a woman from his past… who’s still legally married and has him on the lease to her apartment.
If you’ve ever asked yourself, “Is dating even worth it?” or “Why do women always see me as just a friend?”—this one’s for you.
Expect no-BS advice, clear takeaways, and a deeper understanding of how to navigate real-world dating complications with confidence and clarity.
🔑 You’ll learn:
How to spot emotional red flags before you get too invested
Why being seen as “safe” can kill chemistry—and how to flip the script
What to do when loyalty starts feeling like self-sacrifice
Plus, the results from two powerful polls:
Can you be emotionally available and still have your guard up?
Would you date someone who’s perfect on paper—but there’s no spark?
This episode is raw, real, and packed with practical advice to help you take back control of your dating life.
🎧 Subscribe, rate & review to support the show: https://podcasts.apple.com/us/podcast/just-ask-her-dating-advice-for-single-men/id1782213086
📲 Download free guides at www.datingwithgracie.com/guides
💬 Got a question for a future episode? Submit yours at https://forms.gle/naT2MHcb5vPjU6K68
Episode 25 – Dating Advice for Men Feeling Out of Practice, Out of Options, or Unsure Where They Stand
In this episode of Just Ask Her, Gracie and Tracy respond to three real and relatable listener stories that highlight what so many men are quietly struggling with—feeling behind in dating, unsure how to make a move, or completely lost on what women actually want.
Here’s what we cover:
✅ When you feel like you're doing everything right—and she still chooses someone else
✅ Dating after divorce with zero experience: how to rebuild confidence with women
✅ How to talk to women you’re into (especially when you're not sure if you're moving too fast)
✅ Whether it's ever okay to reach back out after you’ve been rejected
✅ Why defining the relationship early on doesn’t have to be awkward or needy
We also offer specific, judgment-free dating advice for men navigating emotional setbacks, rebuilding after heartbreak, or figuring out how to connect with women authentically in today’s dating world.
If you’ve been wondering where to meet quality women, how to approach someone new, or when to speak up about your feelings—this episode is for you.
Want support in your dating life?
Join the exclusive Dating With Gracie Membership for single men:
👉 https://www.skool.com/dating/about
Want to be featured on the podcast?
Submit your story & question:
👉 [Submit here]
Follow for more honest, no-fluff dating advice:
📲 Instagram | TikTok | YouTube
This week, Gracie and Tracy respond to three real submissions from men who feel like they’re doing everything right—but still struggling in their dating lives.
They talk about what to do when you’re successful on paper but can’t seem to meet women your age, how to recover after giving too much to someone who took advantage of you, and how to date confidently when you feel like a “late bloomer” who’s already behind.
They also break down this week’s polls:
🔸 Do you ever feel like you’re behind in your dating life?
🔸 Does dating really get harder the older you get?
If you’ve ever felt overlooked, used, or unsure how to start again—this one’s for you.
If you want help with your dating life, join the exclusive Dating With Gracie Membership for single men:
https://www.skool.com/dating/about
If you'd like a chance to be featured on the pod, fill out a submission below:
Submit here
Follow for more:
Instagram
TikTok
YouTube
This week, Gracie and Tracy respond to two submissions that hit on a common frustration: putting in effort and still not getting the outcome you want.
They talk about what to do when you keep hearing you're “too sweet” or “a great guy” but still get rejected—and how to handle it when every conversation with a woman feels like a dead end.
They also break down this week’s polls:
🔸 What it really means when a girl says “I’m bad at texting”
🔸 Whether guys still want to meet someone through apps, friends, or a random real-life moment
If you’re tired of wasting your energy on women who aren’t putting in effort—or sick of being the nice guy who never gets the girl—this one’s for you.
If you'd like help optimizing your dating profile, grab Gracie's FREE guide here:
If you want help with your dating life, join the exclusive Dating With Gracie Membership for single men:https://www.skool.com/dating/about
If you'd like a chance to be featured on the pod, fill out a submission below:Submit here
Follow for more:
Instagram
TikTok
YouTube
This week, Gracie and Tracy cover everything from confusing situationships to rebuilding your confidence after divorce.
They unpack how to handle it when she says you're just friends but keeps hooking up with you, whether it's time to give an ultimatum to a girl who's still living with her boyfriend, and how to stop feeling lost when it seems like you don’t belong anywhere.
They also offer guidance to a newly divorced dad who's done being the “nice guy,” but isn’t sure how to date with confidence or what to do after the first few dates.
If you want help with your dating life, join the exclusive Dating
With Gracie Membership for single men:https://www.skool.com/dating/about
If you'd like a chance to be featured on the pod, fill out a submission below:Submit here
Follow for more:InstagramTikTokYouTube
This week, Gracie and Tracy talk about what happens when focusing on self-growth starts to make dating feel… unnecessary, how to handle it when women change your date plans (and whether that’s a secret test), and the pros and cons of dating someone who’s connected to your family through past relationships.
Plus, they react to your votes on this week’s polls—like the most confusing part of dating and whether you'd be open to someone who doesn’t believe in labels.
If you want help with your dating life, join the exclusive Dating With Gracie Membership for single men:https://www.skool.com/dating/about
If you'd like a chance to be featured on the pod, fill out a submission below:Submit here
Follow for more:InstagramTikTokYouTube
This week, Gracie and Tracy dive into three listener submissions.
They talk about what dating feels like after divorce and years off the market, how to handle it when your proposal gets rejected and you're unsure where the relationship stands, and whether it’s worth putting yourself out there when you’re still working on your weight loss goals.
They also react to this week’s poll results on exes—like whether you should be friends, if a birthday text is a bad idea, and what to do when that “I miss you” message hits your phone.
If you want to see the Sea Nymph 3.0, check it out here:
https://youtu.be/aOOHDYXBeOU?si=Iq8L8qZK9siaaQPG
If you want help with your dating life, join the exclusive Dating With Gracie Membership for single men:https://www.skool.com/dating/about
If you'd like a chance to be featured on the pod, fill out a submission below:Submit here
Follow for more:InstagramTikTokYouTube
This week, Gracie and Tracy dive into listener submissions that include: what to do when you feel stuck and scared you’ll never find someone, how to handle your girlfriend grabbing dinner with her ex, and adjusting to dating an ultra-independent woman when you’re used to being the caretaker in the relationship.
They also react to your responses to this week’s polls—including top fears in dating and a list of what women wear that men secretly don’t love. 👀
If you’ve ever struggled with feeling behind in love, questioning your place in a woman’s life, or dealing with mixed emotions around trust and independence—this is your episode.
If you want help with your dating life, join the exclusive Dating With Gracie Membership for single men:https://www.skool.com/dating/about
If you'd like a chance to be featured on the pod, fill out a submission below:Submit here
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