Hosted by Gracie Pleschourt — Dating Coach + Confidence Expert for Men

Just Ask Her - Dating Advice for Single Men

Society EN ↓ 103 episodes

Honest dating advice for single men from two women. Dating expert Gracie Pleschourt (@datingwithgracie on IG) and certified life coach Tracy Pleschourt break down real dating questions, real struggles, and what actually works in modern dating. Each week, they dive into listener-submitted questions about their toughest dating challenges and deliver unfiltered, constructive feedback. Submit yours here: https://forms.gle/34JLMADMcxhqdb7X7

Be sure to visit the podcast's website and support the creator: www.skool.com

Author

Hosted by Gracie Pleschourt — Dating Coach + Confidence Expert for Men

Category

Society

Podcast website

www.skool.com

Latest episode

Nov 4, 2026

Where to listen?

Podcasts in the app Replaio Radio Coming soon

Podcasts are coming to the app soon. Install now and be the first to see a whole new take on podcasts

Get it on Google Play Install for free Android almost 10M downloads · 4.7+ rating iOS soon

Episodes

She's Married... But She's Into Me! Should I Make a Move? (Ep. 101) 04.11.2026

She's Married, But She's Interested... Now What? What do you do when the woman you're falling for is married but possibly heading toward divorce? And where are single guys actually supposed to meet women these days? In Episode 101 of Just Ask Her , hosts Gracie and Tracy tackle two dating dilemmas about attraction, timing, confidence, and creating opportunities for meaningful relations...

What Women REALLY Want! A Single Woman Tells Men the Truth (Ep. 100) 28.10.2026

🎉 EPISODE 100: What Women REALLY Want! Straight From a Single Woman Herself! For 100 episodes, Gracie and Tracy have been answering men's biggest dating questions. But this week, we're doing something different. We're putting a REAL single woman in the hot seat! Meet Jennifer. She's 56, divorced, raising three teenage boys, successful, independent, and ready to find love. So why h...

Is She Losing Interest or Are You Overthinking It? (Ep. 99) 21.10.2026

When should you pursue a woman, when should you back off, and when is it time to take the hint? Dating would be a whole lot easier if everyone came with an instruction manual. Unfortunately, they don't, so Gracie and Tracy are here to help! In Episode 99 of the Just Ask Her Podcast , dating coach Gracie and her mom, Certified Life Coach Tracy, tackle three dating dilemmas involving matching en...

FOUR YEARS Together... And She STILL Won't Commit?! (Ep. 98) 14.10.2026

Are women secretly keeping a roster of men? Is taking a break in a relationship just a nicer way of breaking up? And how long is TOO LONG to wait for someone to finally choose you? This week on the Just Ask Her Podcast , hosts Gracie and Tracy are tackling three dating dilemmas that expose some uncomfortable truths about modern dating, relationship boundaries, emotional availability, and knowing w...

Do Women Really Speak in Code? | Truth or Trash (Ep.2) 11.10.2026

Welcome back to Truth or Trash , the Just Ask Her series where Gracie and Tracy venture into one of the scariest places on the internet: Gracie's social media comment section. This time, they're putting more dating advice, assumptions, hot takes, and questionable internet wisdom to the test. Do women really "speak in code"?  Are women secretly testing men?  Can someone else actually hurt your feel...

We’ve Been Dating 5 Months... I Don’t Know Her Last Name (Ep.97) 07.10.2026

Dating can get complicated fast when fear of rejection, overthinking, mixed signals, and relationship uncertainty start running the show. This week on Just Ask Her , Gracie and Tracy are tackling two dating dilemmas that ultimately come down to one question: Are you willing to risk an uncomfortable answer to finally get some clarity? First, a listener writes in after two divorces and years of rela...

Stop Waiting for Her to Choose You | Dating Advice for Men (Ep.96) 30.09.2026

Are you actually making choices in your dating life, or are you waiting for someone else to make them for you? This week on Just Ask Her, Gracie and Tracy tackle three very different dating dilemmas that all have one thing in common: letting someone else take the driver's seat in your dating life. First, a 25-year-old man is recovering from the end of a nearly five-year relationship and trying...

Stop Trying to Decode Her Mixed Signals (Ep.95) 23.09.2026

Mixed signals are confusing. But at what point do you stop trying to figure out what SHE means and start deciding what YOU actually want? This week on the Just Ask Her Podcast , Gracie and Tracy tackle three dating dilemmas involving mixed signals, fear of rejection, vulnerability, friendship, breakups, and the exhausting habit of trying to decode someone else’s behavior. First, a guy has been tol...

The Fear of Rejection Is Keeping You Single (Ep.94) 16.09.2026

What if the thing you’re doing to protect yourself from rejection is actually keeping you alone? This week on Just Ask Her , Gracie and Tracy tackle three very different dating dilemmas that all have one thing in common: fear. Fear of rejection, fear of getting hurt again, and fear of finally asking the question that could give you the clarity you need. First, a 58-year-old man struggling to move...

TRUTH or TRASH? We React to Men’s Dating Hot Takes 15.09.2026

TRUTH or TRASH? 🗑️ Gracie and Tracy are diving into the comment section, and nobody is safe. In this new Just Ask Her segment, Gracie and Tracy react to dating advice, hot takes, and questionable wisdom pulled straight from Gracie’s social media comments. Should men take dating advice from women? Should women make the first move? Is it okay to approach women at the gym, bar, or out in public? Do “...

Does She Like You? You’re Asking the Wrong Question. (Ep.93) 09.09.2026

What if uncertainty isn’t the problem with dating? What if learning how to handle it is the skill that changes everything? In this episode of Just Ask Her , Gracie and Tracy tackle three dating dilemmas from men at very different stages of life, all struggling with the same thing: trying to know the outcome before taking the next step. First, a great first date turns into mixed signals, canceled p...

When Do You Stop Keeping Your Options Open? (Ep. 92) 02.09.2026

Dating with confidence isn’t about pretending you don’t care. It’s about knowing what you want, communicating honestly, and trusting yourself enough to handle the answer. In this episode of Just Ask Her , Gracie and Tracy answer three dating submissions that look completely different on the surface but share the same underlying challenge: when do you stop protecting your options and actually choos...

The Dating Mindset That’s Keeping You Single (Ep. 91) 26.08.2026

Dating confidence for men isn’t built by never getting rejected—it’s built by trusting yourself regardless of the outcome. In this episode of Just Ask Her , Gracie and Tracy answer three listener dating dilemmas about rejection, insecurity, self-sabotage, and approaching women with confidence. What happens when you assume women will reject you because of your height? Are you protecting yourself fr...

How to Approach Women Without Being Creepy (Ep. 90) 19.08.2026

Join the 30 Day Rizz Challenge at https://www.skool.com/rizz-challenge/about How do you approach women without being creepy? The difference often isn't whether you approach—it's how you handle the moments leading up to it. In this episode of Just Ask Her , Gracie shares a grocery-store encounter that started with prolonged staring and eventually turned into an approach in the parking garag...

What Women Actually Want: Real Dating Advice for Men (Ep. 89) 12.08.2026

What do women actually want when dating? We asked real women the dating questions men want answered—from how to approach women to first dates, texting, dating profiles, and more. In this special episode of Just Ask Her , Gracie and Tracy take the podcast to Country Jam 2026 to hear real, unscripted answers from women of different ages. If you're a single man trying to date with more confidence...

How to Handle Relationship Conflict Without Losing Connection (Ep. 88) 05.08.2026

Looking for summer first date ideas that actually help build attraction? In this episode of Just Ask Her , Gracie and Tracy share creative date ideas before diving into two powerful listener questions about repairing relationship conflict and dating after heartbreak.  Whether you're struggling to communicate during conflict, wondering how to validate your partner's emotions, or questioning...

Are These Dating Red Flags... or Are You Overthinking Them? (Ep. 87) 29.07.2026

What are the biggest dating red flags in women—and which ones actually aren't red flags at all? In this episode of Just Ask Her , Gracie and Tracy break down common assumptions men make while dating and explain why context matters more than quick judgments. They also answer real listener submissions about mixed signals after a promising first date, overcoming the feeling of being "behind&...

You're Not Behind: The Truth About Dating, Breakups, & Commitment (Ep. 86) 22.07.2026

Wondering whether to text your ex, when to commit, or why dating feels so difficult? This episode explores healthy dating, emotional growth, and dating confidence for men navigating modern relationships. Gracie and Tracy answer three thoughtful listener questions covering breakups, dating uncertainty, and healing from childhood experiences that continue to affect relationships today. Whether you&#...

Why Your Dating Mindset Matters More Than You Think (Ep. 85) 15.07.2026

Are your dates feeling one-sided? In this episode of Just Ask Her , Gracie and Tracy tackle one of the most common dating frustrations for men: feeling like you're doing all the work in conversation and wondering whether women actually want to get to know you. They also answer a listener's question about whether women have an advantage in modern dating, discuss why mindset matters more tha...

Confidence Isn't Something You Find, It's Something You Build (Ep. 84) 08.07.2026

Confidence with women isn't something you're born with—it’s something you build through action. In this episode, Gracie and Tracy break down dating confidence, rejection, social anxiety, and why trying to become "what women want" is holding so many men back. If you've ever overanalyzed a rejection, struggled to approach women in person, or wondered why dating feels so confusi...

How to Know When a Relationship Isn't Right (Ep. 83) 01.07.2026

Ever wonder whether you're reading the signs correctly—or holding onto a relationship that's no longer moving forward? In this episode of Just Ask Her , Gracie and Tracy answer three real dating submissions from men navigating complicated relationship dynamics. From mixed signals with a coworker to becoming someone's emotional rescuer and exploring unconventional relationship structure...

How to Rebuild Trust After Emotional Betrayal in a Relationship (Ep. 82) 24.06.2026

Trust, honesty, and relationship values are at the center of this episode of Just Ask Her . We answer three real dating questions from listeners navigating betrayal, dating apps, and faith-based relationships. First, we discuss whether trust can be rebuilt after a partner secretly continues communicating with someone from their past. Then we tackle a dating app dilemma involving age misrepresentat...

Dating Isn't the Problem—You're Using the Wrong Playbook (Ep. 81) 17.06.2026

Dating with low self-esteem, autism traits, OCD, or years of rejection can feel impossible—but what if the problem isn't you? In this episode of Just Ask Her , Gracie and Tracy respond to a powerful listener submission from a 26-year-old man who feels like dating was stacked against him from the start. They discuss self-worth, attraction, neurodivergence, confidence, and why changing your dati...

Dating Burnout, Breakups & Moving On: What Men Need to Hear (Ep. 80) 10.06.2026

Feeling stuck in your dating life? Whether you're constantly getting friend-zoned, struggling with dating burnout, or trying to move on after a breakup, this episode breaks down the mindset shifts that can help you regain confidence and take control of your dating journey. Gracie and Tracy answer real listener submissions from men navigating long-term singleness, heartbreak, and the challenge...

How to Overcome Approach Anxiety in Dating (Ep. 79) 03.06.2026

Approach anxiety, fear of rejection, and limiting beliefs are keeping too many men stuck in modern dating. In this episode of Just Ask Her , Gracie and Tracy break down how men can build real confidence, stop pre-rejecting themselves, and create meaningful connections in dating.  From navigating political and religious differences to dating as a divorced dad, this episode is packed with practical...

Listen to the Just Ask Her - Dating Advice for Single Men podcast in Replaio

Radio and podcasts in one app - free, with no sign-up. Install today and do not miss the launch

Get it on Google Play

Replaio is not a podcast publisher; show names, artwork and audio belong to their authors and are distributed through public RSS feeds.