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Just Ask Her - Dating Advice for Single Men

Just Ask Her - Dating Advice for Single Men

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

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

95 - The Fear of Rejection Is Keeping You Single (Ep.94)
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  • 95 - 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



    Wed, 16 Sep 2026 - 56min
  • 94 - 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 


    Tue, 15 Sep 2026 - 22min
  • 93 - 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 


    Wed, 09 Sep 2026 - 47min
  • 92 - 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


    Wed, 02 Sep 2026 - 56min
  • 91 - 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


    Wed, 26 Aug 2026 - 48min
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