Just Ask Her - Dating Advice for Single Men

Hosted by Gracie Pleschourt — Dating Coach + Confidence Expert for Men
  • 4.8 (65)
  • Relationships
  • Updated Weekly

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

  1. 3d ago

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

    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 told very clearly that she DOESN’T want to date him... except she keeps kissing him. Repeatedly. So what exactly are you supposed to believe when her words say “no” but her actions keep handing you a “maybe”?  Next, a listener realizes he has a habit of rejecting himself before a woman ever gets the chance. When a promising long-distance connection suddenly goes quiet, he assumes the worst and emotionally checks out. Plot twist: she comes back asking where HE stands.  Finally, after the end of a seven-year relationship, one listener develops feelings for the female friend who helped him through the breakup. Is she interested? Is he rebounding? Is he even ready for another relationship? And should he be trying to decode her mixed signals when he already admits he isn't ready to date?  Plus, Tracy explains what being a certified life coach actually means, Gracie talks about how life coaching tools helped transform her own dating experience, and somehow the phrase “have your cake and eat it too” sends the entire episode into an important investigation of cake, chocolate, peanut butter, Dairy Queen ice cream cakes, and why anyone would acquire cake without intending to eat it. If you struggle with dating anxiety, mixed signals from women, fear of rejection, overthinking dating, dating confidence, setting boundaries, emotional regulation, vulnerability, self-rejection, relationship anxiety, getting over an ex, understanding women, or knowing when to move on, this episode is for you. Just Ask Her helps single men stop guessing, date with confidence, understand themselves better, build healthier relationships, and connect with real women without turning every text, kiss, silence, or vague “maybe” into a full-scale criminal investigation. And since apparently this is important now: What’s your favorite kind of cake? Drop it in the comments. 🎂 Self-Made Man Dating Journal -  https://self-made-u.myshopify.com/products/self-made-man-dating-journal?utm_source=copyToPasteBoard&utm_medium=product-links&utm_content=web Coupon code: JUSTASKHER Submission Form: https://forms.gle/e7LTvCkT1fhkFQEF8 Join the 30 Day Rizz Challenge waitlist at: https://datingwithgracie.com/rizz-challenge-live Chapters: 00:00 Mixed Signals or Your Decision? 00:49 Welcome to Just Ask Her 01:04 What Is a Certified Life Coach? 03:40 What Makes a Dating Expert? 05:01 Why Dating Is Hard for Everyone 07:14 Fear of Rejection Starts Here 09:07 The Real Dating Problem 10:54 Submission #1: She Keeps Kissing Me 12:24 Okay... We’re Confused Too 13:16 Set a Boundary or Move On 15:13 Words vs. Actions 16:58 Why Does She Keep Kissing Him? 18:24 The Dopamine Hit of “Maybe” 19:17 Stop Trying to Explain Her 20:41 Submission #2: He Rejected Himself 22:16 The Self-Rejection Trap 23:58 Ignoring the Signs She Likes You 24:31 What Do YOU Want? 25:43 Vulnerability Builds Trust 27:34 The Self-Made Man Dating Journal 28:44 Submission #3: Friend or Rebound? 30:05 Stop Trying to Force It 31:37 When Are You Ready to Date Again? 33:25 Ask Her on an Actual Date 34:14 “You’re Special” Means What? 35:04 What Do You Want Next? 36:50 Somehow We’re Talking About Cake 39:32 Send Us Your Dating Dilemma #DatingAdvice #DatingAdviceForMen #RelationshipAdvice #DatingConfidence Keywords: mixed signals from women, dating advice for men, how to know if she likes you, understanding women, fear of rejection, dating confidence, dating anxiety, self-rejection in dating, relationship advice for men, dating podcast for men

  2. Sep 16

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

    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 on after betrayal and infidelity ended a relationship he still can’t stop thinking about. How do you rebuild trust, stop comparing new women to an ex, and open yourself up to love again after heartbreak? Next, a divorced man travels from San Diego to Zurich to visit a longtime female friend after their connection begins feeling like something more. But when he finally brings up a long-distance relationship, everything changes. Did he misread the signs, or is this exactly why honest communication and choosing clarity over guessing matter so much in dating? Finally, a 56-year-old man who has never been on a date admits he intentionally pursues unavailable women because he’s terrified of rejection. Gracie and Tracy break down why avoiding rejection can become a self-fulfilling cycle, how your brain turns fear into evidence that you “can’t” date, and why learning to tolerate uncomfortable emotions can completely change your dating life. Plus, Gracie and Tracy discuss the controversial Callaway Golf ad, their family trip to Seattle, and somehow end up debating whether “Rick Hopper” is secretly a Stranger Things character. If you’re struggling with dating anxiety, fear of rejection, getting over an ex, infidelity, heartbreak, dating after divorce, approaching women, the friend zone, long-distance relationships, building confidence with women, emotional availability, relationship anxiety, or finding a healthy relationship, this episode is for you. Just Ask Her helps single men date with confidence, understand women, build genuine connections, and create healthier relationships without playing games or pretending to be someone they’re not. Have a dating dilemma of your own? Submit it using the link in the show notes, and Gracie and Tracy may answer it on a future episode. Self-Made Man Dating Journal -  https://self-made-u.myshopify.com/products/self-made-man-dating-journal?utm_source=copyToPasteBoard&utm_medium=product-links&utm_content=web Submission Form: https://forms.gle/e7LTvCkT1fhkFQEF8 Take the Rizz Quiz: https://datingwithgracie.com/dwgrizzquiz Chapters: 00:00 Fear of Rejection 01:05 Welcome Back 02:23 Seattle Adventures 08:22 The Callaway Controversy 13:27 When a Joke Goes Too Far 19:47 Submission #1: Betrayal 21:28 Facts vs. the Story 25:16 Letting Go of an Ex 28:51 Betrayal Is Not a Life Sentence 31:48 Rebuilding Confidence 33:29 Submission #2: More Than Friends? 36:03 Did He Misread the Signs? 37:15 Ask for Clarity 41:13 What Does She Represent? 43:17 Find Someone Who Chooses You 45:20 Submission #3: Never Been on a Date 46:37 Afraid to Actually Date 48:29 Facing Rejection 49:21 Gracie's Fear of Public Speaking 51:11 Learning to Feel the Fear 54:10 One Approach Can Change Everything 55:08 Send Us Your Dating Dilemmas #DatingAdvice #DatingAdviceForMen #RelationshipAdvice #DatingConfidence  Keywords: dating advice for men, fear of rejection, dating confidence, relationship advice for men, how to approach women, how to talk to women, how to get over an ex, dating after divorce, emotionally unavailable women, fear of dating

  3. Sep 15

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

    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 “high quality women” get the ick? And apparently, should every single man just get a dog? Some takes are truth. Some are trash. And some earn a spicy rant. If you’re a single man navigating modern dating, approaching women, making the first move, building confidence, or trying to separate good dating advice from absolute garbage, welcome to Truth or Trash. #DatingAdvice #DatingAdviceForMen #ModernDating #TruthOrTrash

  4. Sep 9

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

    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 plans, Instagram comments, and silence. Is she genuinely interested or stringing him along?  Next, a 49-year-old listener struggling with social anxiety asks how to become more attractive to women. But his real challenge might not be attraction at all.  Finally, a 23-year-old wants to turn a college friendship into something more without making things awkward. Should he tell her he’s interested? How much should they text first?  Plus, Gracie shares an incredible dating story involving a bachelorette party, country dancing, a Pitbull costume, a bald cap, a wrong phone number, and some impressive LinkedIn detective work. Whether you’re dealing with mixed signals, dating anxiety, rejection, overthinking, texting, approaching women, asking someone out, building confidence, or figuring out if she likes you, this episode is about getting comfortable with not knowing what happens next. Because dating confidence isn’t knowing she’ll say yes. It’s knowing you’ll be okay with the answer either way. Have a dating dilemma? Submit yours for a chance to be featured on a future episode. Self-Made Man Dating Journal -  https://self-made-u.myshopify.com/products/self-made-man-dating-journal?utm_source=copyToPasteBoard&utm_medium=product-links&utm_content=web Submission Form: https://forms.gle/e7LTvCkT1fhkFQEF8 Join the 30 Day Rizz Challenge at https://www.skool.com/rizz-challenge/about Chapters: 00:00 Stop Chasing Certainty 01:00 Welcome to Just Ask Her 01:31 Baseball & Concerts 05:53 The Pitbull Love Story 14:30 Submission #1: Mixed Signals 16:22 Did He Mess Up? 17:41 Is She Stringing Him Along? 20:52 Why Mixed Signals Hook You 21:50 Are You Missing Her? 24:15 Should He Give Her Another Chance? 25:24 The Self-Made Man Dating Journal 26:34 Submission #2: Fear of Rejection 27:35 Attraction vs. Avoidance 29:18 Why Asking Women Out Feels Terrifying 30:28 Building Social Confidence 32:01 Redefining Dating Success 33:18 How to Handle Rejection 36:25 Stop Waiting for Certainty 37:00 Submission #3: Friends to Dating 38:52 Should He Ask Her Out? 40:25 You’re Not Supposed to Know 42:18 Can Friendship Become Romance? 43:47 Stop Overthinking Texting 45:25 How Much Should You Text? 46:34 Final Thoughts #DatingAdvice #DatingAdviceForMen #RelationshipAdvice #DatingConfidence

  5. Sep 2

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

    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 choose? One man is considering reaching back out to an ex after a major mistake damaged trust. Another is afraid that asking the woman he’s dating “what are we?” will make him look needy. And another has finally created abundance in his dating life—only to discover that choosing between multiple great women brings a new challenge. They break down what real confidence looks like, why clarity is better than trying to control an outcome, how to approach exclusivity, and why dating successfully eventually requires the courage to make a decision. Time Stamps / Chapters:  03:58 Why Charisma Is a Skill You Can Build 09:29 The Rise Challenge and Building Charisma 12:37 What Charisma Looks Like in Real Life 15:13 How the 30-Day Charisma Challenge Works 17:55 Three Dating Dilemmas With One Common Problem 18:46 Should You Reach Back Out to an Ex? 20:35 Why You Need to Disclose That You’re a Dad 28:59 Should He Actually Send the Message? 36:01 How to Have the “What Are We?” Conversation 38:07 What Real Dating Confidence Looks Like 43:13 Clarity, Exclusivity, and Fear of Losing Her 45:29 How to Choose Between Multiple Women 50:31 How to Know Who You Actually Want 53:23 When to Stop Dating Multiple People Join the 30 Day Rizz Challenge at https://www.skool.com/rizz-challenge/about Self-Made Man Dating Journal -  https://self-made-u.myshopify.com/products/self-made-man-dating-journal?utm_source=copyToPasteBoard&utm_medium=product-links&utm_content=web Submission Form: https://forms.gle/e7LTvCkT1fhkFQEF8 Apply to work with us: https://api.leadconnectorhq.com/widget/bookings/dwg-consultation-call #DatingAdvice #DatingForMen #Relationships Keywords: dating advice for men dating with confidence relationship clarity when to become exclusive dating multiple women how to choose a partner confidence versus neediness what are we conversation dating abundance mindset intentional dating for men how to contact an ex should I text my ex commitment in dating choosing the right woman relationship advice for men

  6. Aug 26

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

    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 from dating because a past relationship hurt you? And what do you do when you’ve made huge improvements socially but still feel like you’re failing? Gracie and Tracy break down the beliefs underneath these struggles and explain how to stop making your self-worth dependent on whether a woman chooses you. They discuss vulnerability, charisma, emotional availability, approaching women, “out of my league” thinking, and learning to measure dating progress by how you show up—not just by whether you get a relationship. This episode is for single men who are tired of overthinking dating, fearing rejection, or feeling like they have to prove they’re good enough. Join the 30 Day Rizz Challenge at https://www.skool.com/rizz-challenge/about Time Stamps / Chapters: 00:40 Welcome to Just Ask Her 00:55 The Odyssey, movies & what they’re watching 09:37 Help Just Ask Her reach more single men 09:56 JJ: Dating and rejection because of height 11:22 Stop trying to prove your worth on dates 14:29 The reality of height preferences in dating 18:28 Stop predicting rejection before you approach 20:12 Rejection vs. values and relationship compatibility 25:08 Self-made Man Dating Journal 26:16 Coach Trey: Is he self-sabotaging his dating life? 28:05 When self-sabotage is actually self-protection 37:03 Ryan: Growing socially but still feeling like a failure 40:26 Build confidence without moving the goalposts #DatingAdvice #DatingConfidence #MensDatingAdvice

  7. Aug 19

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

    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 garage. She explains exactly what was going through her mind as the interaction unfolded—and why the man's hesitation made an apparently well-intentioned approach feel increasingly unsafe.  Gracie and Tracy use the experience to break down a better way to start conversations with women: stop searching for the perfect line, pay attention to context, read the situation, and learn how to have normal conversations with new people. This episode is for men who want to become more confident approaching women without making interactions feel forced, rehearsed, or uncomfortable. Time Stamps: 00:31 Welcome to Just Ask Her 01:10 Why This Approach Story Matters 11:27 The Grocery Store Encounter Begins 13:19 How to Make Eye Contact Without Being Creepy 15:17 The First Red Flag 18:33 When Awkward Attention Starts Feeling Unsafe 21:07 The Self-Checkout Encounter 23:28 He Approaches Her in the Parking Garage 28:29 Why Waiting Too Long to Approach Backfires 33:20 What He Should Have Done Instead 36:35 There Is No Perfect Opener 39:49 How Women Actually Want Men to Approach 42:41 Approaching Is Really a Social Skill #DatingAdvice #DatingForMen #SocialSkills Keywords: how to approach women approaching women without being creepy how to talk to women how to start conversations dating advice for men conversation starters with women confidence approaching women how to meet women social skills for men charisma for men natural conversation starters approaching women in public how women want to be approached dating confidence for men become more charismatic

  8. Aug 12

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

    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, this episode gives you a firsthand look at women's perspectives. You'll hear what women notice when a man approaches them, what makes a positive impression, what turns them off on dating apps, and how they want a guy to take the next step. One of the biggest themes? Context matters. Preferences aren't universal, but the conversations reveal recurring themes around confidence, respect, authenticity, effort, intentionality, and actually getting to know someone. Self-Made Man Dating Journal -  https://self-made-u.myshopify.com/products/self-made-man-dating-journal?utm_source=copyToPasteBoard&utm_medium=product-links&utm_content=web Submission Form: https://forms.gle/e7LTvCkT1fhkFQEF8 Join the 30 Day Rizz Challenge at https://www.skool.com/rizz-challenge/about Apply to work with us: https://api.leadconnectorhq.com/widget/bookings/dwg-consultation-call Time Stamps / Chapters: 00:00 What women actually think about dating 11:20 Taking Just Ask Her to Country Jam 13:56 What surprised Gracie and Tracy 24:42 Where women prefer to meet men 27:50 Small things that win women over 30:56 How to approach a woman with her friends 35:13 Dating profile mistakes women notice 39:59 Should you ask for her number? 43:19 How long should you wait to ask her out? 47:08 What makes a good first date? 54:09 Final thoughts on the special episode #DatingAdvice #DatingTipsForMen #WhatWomenWant

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4.8
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65 Ratings

About

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

Information

  • Creator
    Hosted by Gracie Pleschourt — Dating Coach + Confidence Expert for Men
  • Years Active
    2024 - 2026
  • Episodes
    96
  • Rating
    Explicit
  • Copyright
    © Hosted by Gracie Pleschourt — Dating Coach + Confidence Expert for Men
  • Show Website
    Just Ask Her - Dating Advice for Single Men

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