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Just Ask Her - Dating Advice for Single Men

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

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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
54 Episodes
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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 contextsHow to handle mixed signals and trust your instincts after being hurtWhy ghosting and rejection don’t define your worthThe hidden pitfalls of dating apps and how to reframe “rejection”Building confidence and self-awareness for better connectionsPlus, 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: @datingwithgracieNew episodes every Wednesday!You’ll learn:When (and how) to approach women respectfully—alone or in groupsWhy ghosting and rejection aren’t reflections of your worthHow to trust your instincts and set healthy boundariesThe truth about dating apps and self-sabotaging beliefsActionable tips for self-awareness and authentic connectionPlus, 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-TrustIn 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!
Welcome to the anniversary episode of Just Ask Her! Gracie and Tracy celebrate a full year of empowering single men with honest, actionable dating advice. In this special episode, they reflect on the journey so far, the growth of their community, and the impact the show has had on listeners around the world.To mark the occasion, Gracie and Tracy take your most-asked dating questions out of the studio and into the real world—specifically, the Mall of America! Hear candid, unfiltered answers from women of all ages and backgrounds as they share what really matters in dating, what green and red flags they look for, and their best advice for men looking to improve their love lives.Highlights:The story behind the podcast’s evolution and its first anniversaryWhy men’s vulnerability and willingness to seek advice is so powerfulThe importance of mindset and community in dating successOn-the-street interviews with women answering your top dating questions:Most attractive qualities in a manApproaching women: what works and what doesn’tDating apps vs. real life vs. mutual friendsHeight, self-improvement, and who should pay for the first dateBiggest red and green flagsThe best advice for single menReflections on the value of honest conversations and the supportive Just Ask Her communityResources: Self-Made Man Dating Journal – Available on Amazon ⁠⁠Submit your questions for future episodes via the show’s submission form⁠ Dating Differently Application Thank you for being part of our journey! If you’ve found value in the show, the best anniversary gift you can give is to share this episode with someone who needs it and leave us a review. Here’s to many more years of real talk and real results!It’s our one-year anniversary! To celebrate, Gracie and Tracy take your most-asked dating questions to the Mall of America, getting honest answers from real women. Tune in for fresh perspectives, heartfelt reflections, and practical advice that will help you date with confidence. Don’t miss this special episode packed with insights, laughs, and gratitude for our amazing community. Share, review, and keep your questions coming—because no matter where you are, you can always Just Ask Her.
Episode 51: Breaking Patterns & Building Self-Trust in DatingDescription:In this episode of "Just Ask Her," Gracie and Tracy dive into three listener submissions that highlight the real challenges men face in modern dating. From navigating attachment styles and dating app fatigue to finding emotionally available partners and breaking free from self-sabotaging patterns, this episode is packed with actionable advice and heartfelt coaching. Plus, Gracie announces the launch of the Self-Made Man Dating Journal, designed to help single men reflect, grow, and date with intention.Show Notes:Intro & Halloween BanterGracie and Tracy kick off the episode with some lighthearted Halloween talk, sharing personal stories and family traditions.Submission 1: Sal’s StorySal, a father of four and firefighter, shares his journey from anxious to secure attachment style.Struggles with dating app fatigue and finding emotionally available women.Gracie and Tracy discuss the pitfalls of over-labeling attachment styles, the scarcity mindset, and the importance of real-life connections.Advice: Leverage your strengths in real-world environments, seek shared purpose, and remember that every "failed" connection brings you closer to alignment.Submission 2: Kyle’s QuestionKyle wonders why it seems women don’t have hobbies and how to meet like-minded singles.Discussion on generational trends, burnout, and the importance of reframing blanket statements.Tips: Switch up your social activities, challenge self-sabotaging beliefs, and remember that the right partner will appreciate your diverse interests.Submission 3: Greg’s PatternGreg, an Australian Air Force sergeant, describes a recurring pattern of women pulling away.Gracie and Tracy explore confirmation bias, self-trust, and the importance of detaching from painful narratives.Practical steps: Name the pattern neutrally, detach from identity, decide what you’ll do differently, and let people reveal themselves over time.Resource Mentioned:Self-Made Man Dating Journal – Now available on Amazon! Designed to help single men track dates, reflect, and grow. Limited first run—grab yours before they’re gone.Listener Call to Action:If you enjoy the show, please rate and review on Spotify or Apple Podcasts, and share with friends!Submit your questions for future episodes.Self-Made Man Dating Journal – Available on Amazon ⁠⁠Submit your questions for the anniversary episode via the show’s submission form⁠ Connect with Gracie:Instagram & TikTok: @datingwithgracieNew episodes every Wednesday!
Episode 50: Real Dating Questions Answered – Confidence, Signals & Starting OverDescription:In this milestone 50th episode of Just Ask Her, dating expert Gracie Pleschourt and certified life coach Tracy Pleschourt tackle real listener questions about modern dating. From overcoming shyness and reading signals to building confidence and starting over after a long relationship, Gracie and Tracy deliver no-nonsense advice straight from a woman’s perspective. Plus, they announce the launch of the Self-Made Man Dating Journal and tease a special anniversary episode coming soon!Whether you’re struggling to approach someone new, wondering how to get noticed, or navigating the dating scene after years away, this episode is packed with practical tips, research-backed insights, and encouragement to help you take control of your dating life.Show Notes:00:00 – Welcome & Introduction01:30 – Listener Submission #1: Should I ask out the Home Depot girl?05:00 – How to read signals vs. friendly behavior08:30 – Building confidence and taking action despite shyness12:00 – The truth about rejection and courage in dating15:00 – Launch Announcement: Self-Made Man Dating Journal18:00 – Listener Submission #2: Why don’t women notice me?22:00 – The science of attraction and nonverbal cues25:00 – How to shift from seeking validation to radiating confidence29:00 – Listener Submission #3: Dating after a 30-year relationship33:00 – Navigating small communities and changing your identity37:00 – Advice for starting over and expanding your social circles41:00 – Anniversary Episode Teaser: “Man on the Street” Q&A44:00 – How to submit your questions for the special episode46:00 – Final thoughts & where to find Gracie onlineResources Mentioned:Self-Made Man Dating Journal – Available on Amazon Submit your questions for the anniversary episode via the show’s submission form Follow Gracie on Instagram & TikTok: @datingwithgracieIf you enjoyed this episode, please rate and review Just Ask Her on Spotify or Apple Podcasts, and share it with your friends!
Episode 49: Ghosted, Blocked, and Bouncing Back — Real Dating Dilemmas & Self-Made Man AdviceEpisode Description:Are you tired of feeling stuck in your dating life, confused by mixed signals, or left wondering why she ghosted you? In this episode of Just Ask Her, dating expert Gracie Pleschourt and certified life coach Tracy Pleschourt tackle real listener submissions about ghosting, blocking, and the emotional rollercoaster of modern dating.From decoding sudden disappearances to reframing rejection and building emotional resilience, Gracie and Tracy offer no-nonsense advice straight from a woman’s perspective. They break down the “self-made man” mindset, share practical tips for handling heartbreak, and answer tough questions about honesty, closure, and moving forward.Plus, enjoy a fun behind-the-scenes recap of their recent trip to Ireland, complete with cultural takeaways and travel mishaps!Show Notes:0:00 – Welcome & Introduction: Why dating feels so confusing today2:30 – Listener Submission #1: Why did she ghost and block me after a great date? 18:00 – The “Self-Made Man” Mindset 25:00 – Listener Submission #2: “Why do I feel like I’m preparing women for other men?” 38:00 – Listener Submission #3: “Should I tell women my ex-wife is a lesbian?” 48:00 – Product Spotlight: The Self-Made Man Dating Journal 52:00 – Ireland Recap: Banter, culture shocks, and travel lessons 1:05:00 – Final Thoughts & How to Work with Gracie and Tracy Resources Mentioned:The Self-Made Man Dating Journal (available on Amazon)Application link for coaching https://form.typeform.com/to/zJkel6VK?utm_source=xxxxxFollow Gracie on Instagram & TikTok: @datingwithgracieSubscribe for new episodes every Wednesday!
Dating After Divorce – Confidence, Apps & Real Connections for Men Over 40 Ep. 48Hosts: Gracie Pleschourt & Tracy PleschourtIn This Episode:[00:00] Welcome & Introduction[01:30] Listener Question: Starting Over After Divorce at 45 Breaking old routines and building new momentumIs there a “market” for divorced men over 40?How to meet new women and rebuild your social circleThe fastest-growing demographic on dating appsThe importance of self-awareness: knowing what you want and what you bring to the tableTips for getting comfortable with dating appsHow to treat dating as research, not a performance[18:00] The Self-Made Man Dating Journal Launch How journaling can help you track progress and avoid repeating old patternsBuilding confidence and clarity through reflectionWhere to get the journal (Amazon link in show notes)[22:00] Listener Question: Revealing a Physical Difference (Amputee Experience) How to talk about insecurities and physical differences with confidenceWhy your story and self-acceptance matter more than “the reveal”The power of vulnerability and authenticity in dating[30:00] Listener Question: Competing for Women’s Attention Why confidence and self-value matter more than “winning” attentionShifting from scarcity to abundance mindsetPractical tips to stand out: eye contact, conversation, and authenticityHow to become unforgettable by making women feel seen and at ease[40:00] Final Thoughts & Where to Find Gracie Follow Gracie on Instagram & TikTok: @datingwithgracieApply for 1:1 coaching (link in show notes)Rate & review the podcast on Spotify or Apple PodcastsResources Mentioned:Self-Made Man Dating Journal https://www.amazon.com/dp/B0F9B7M5B3?th=11:1 Coaching Application https://gracie.clickfunnels.com/optin1758810316648Follow Gracie: Instagram & TikTok @datingwithgracieSubscribe for new episodes every Wednesday!
Are you tired of feeling like someone’s backup plan in your dating life? In this episode of Just Ask Her, dating expert Gracie Pleschourt and certified life coach Tracy Pleschourt tackle real listener questions about complicated romantic situations, building self-confidence, and setting healthy boundaries.From navigating “work spouse” dynamics and emotional gray areas to overcoming social anxiety with women and learning to trust yourself after heartbreak, Gracie and Tracy offer no-nonsense advice to help you take control of your love life. Whether you’re struggling to move on from a relationship, worried about making social mistakes, or wondering if you should pursue someone who’s already taken, this episode is packed with actionable insights and tough love.Show Notes:[00:00] Welcome & Updates: Gracie and Tracy share personal updates, including an upcoming trip to Ireland and behind-the-scenes podcast planning.[04:00] Listener Submission #1: “Am I the Second Option?” — Advice for men caught in complicated relationships, why pursuing someone who’s unavailable is a losing game, and how to protect your self-respect.[18:00] The Self-Made Man Dating Journal Launch: Introducing a new tool for single men to track, reflect, and improve their dating experiences.[20:00] Listener Submission #2: “Social Mistakes with Women” — How to handle awkwardness, why confidence is really about self-trust, and why women care less about your blunders than you think.[35:00] Listener Submission #3: “Trust Issues After a Breakup” — Rebuilding trust in yourself, letting go of relationships that no longer serve you, and why your future happiness depends on your own decisions.[50:00] Key Takeaways: Why boundaries, self-awareness, and emotional resilience are the real keys to dating success.[52:00] Call to Action: Rate, review, and share the podcast; follow Gracie on Instagram and TikTok @datingwithgracie.Resources Mentioned:The Self-Made Man Dating Journal: Follow Gracie on Instagram and TikTok: @datingwithgracieIf you enjoyed this episode, please rate us on Spotify or Apple Podcasts and share with your friends! Got a question for Gracie and Tracy? Submit it for a chance to be featured in a future episode.
Are you tired of feeling stuck in your dating life, striking out on dating apps, or wondering why nothing seems to work? In this episode, dating expert Gracie Pleschourt and certified life coach Tracy Pleschourt answer real listener questions and share no-nonsense advice to help men attract the women they want and build lasting confidence.What You’ll Learn:Why dating apps might not be working for you—and what to do insteadThe mindset shifts that turn “invisible” guys into irresistible partnersHow to break free from self-sabotaging beliefs and rewrite your dating storyPractical tips for meeting women in real life (and why it’s often more effective than apps)How to stand out at speed dating events and make a memorable first impressionThe truth about confidence, self-worth, and why women are drawn to men who trust themselvesHow to handle rejection, scarcity mindset, and the pressure to “have it all figured out”Listener Questions Answered:“I’ve been on dating apps for 20 years with no luck. What am I doing wrong?”“How do I prep for a speed dating event and avoid the friend zone?”“Why do I feel like every woman is already taken, and how do I stop feeling average?”Special Segment:Introducing the Self-Made Man Dating Journal—your new tool for tracking dates, building self-awareness, and making real progress in your love life. Limited batch available on Amazon—grab yours before they’re gone!Join the Conversation:Take our poll on Spotify and let us know: Do you love the personal banter, or do you prefer us to get straight to the dating advice?Share your thoughts and questions for future episodes!Connect with Gracie:Instagram & TikTok: @‌datingwithgracieCheck out Gracie’s membership for hands-on coaching and support https://form.typeform.com/to/zJkel6VK?utm_source=xxxxxIf you enjoyed this episode, please rate us on Spotify or Apple Podcasts and share with a friend!No matter where you are or what your situation is—just ask her.Timestamps:00:00 – Welcome & Listener Feedback06:00 – Why Dating Apps Aren’t Working18:00 – Mindset Shifts for Dating Success30:00 – Real-Life Dating Tips & Speed Dating Advice45:00 – Overcoming Scarcity and Building Confidence55:00 – Introducing the Self-Made Man Dating Journal60:00 – Final Thoughts & Calls to ActionResources Mentioned:Self-Made Man Dating Journal https://www.amazon.com/dp/B0F9B7M5B3?th=1Gracie’s Membership https://form.typeform.com/to/zJkel6VK?utm_source=xxxxx
Break the Cycle: Real Advice for Dating Confidence, Moving On, and Finding LoveEpisode 45 – Just Ask Her PodcastEpisode Summary:In this episode, Gracie and Tracy tackle some of the most common and challenging dating dilemmas sent in by listeners. From navigating on-again, off-again relationships to overcoming self-doubt and building confidence, this episode is packed with real talk and actionable advice for anyone looking to level up their love life.What You’ll Learn:How to recognize and break free from unhealthy relationship cyclesWhy you can’t “save” someone else—and how to set healthy boundariesThe truth about attraction, self-image, and why confidence matters more than looksHow to handle rejection, negative comments, and the pressure of dating appsPractical tips for moving on after heartbreak and getting back into the dating sceneWhen to follow up (and when to move on) in online dating conversationsWhy chemistry on the first date isn’t everything—and what to focus on insteadListener Submissions Featured:Todd: Struggling with an on-again, off-again relationship and wondering if he should wait or move onDrew: Battling self-confidence issues and negative feedback while re-entering the dating worldAnonymous: Unsure about next steps after a breakup and facing challenges with dating apps and first datesSpecial Segment:Gracie and Tracy announce the launch of the Self-Made Man Dating Journal—designed to help single men track their dating experiences, reflect, and grow. Limited quantities available on Amazon!Resources & Links:Self-Made Man Dating Journal on AmazonConnect with Gracie on Instagram and TikTok: @‌datingwithgracieSupport the Show:If you enjoyed this episode, please rate and review us on Spotify or Apple Podcasts, and share with your friends!New episodes every Wednesday. No matter where you are or what your situation is—just ask her.
Episode 44: Living at Home, Gym Love, and Mixed SignalsHosts: Gracie Pleschourt & Tracy PleschourtStruggling with dating while living at home? Unsure if you should make a move at the gym? Confused by mixed signals from someone you like? In this episode of Just Ask Her, dating expert Gracie Pleschourt and certified life coach Tracy Pleschourt tackle your toughest questions with no-nonsense, real-world advice.We answer listener submissions about:How to date confidently when you’re not financially independent or still living with your parentsNavigating the tricky world of gym romance and whether you should look for love outside your workout routineWhat to do when someone gives you mixed signals after turning you downKey Takeaways:Confidence and clarity about your life path are more attractive than financial status.Don’t apologize for your situation—own your story and values.Mixed signals usually mean “no”—don’t wait around for someone to change their mind.The gym isn’t the only place to meet active partners; try apps, clubs, and social events.Focus on what you can control and keep your dating mindset positive.Connect with Gracie:Instagram & TikTok: @datingwithgracieSupport the Show:Rate and review on Spotify or Apple PodcastsShare this episode with friendsPurchase the Self-Made Man Dating Journal:https://www.amazon.com/dp/B0F9B7M5B3?th=1New episodes every Wednesday!
Episode 43: Stood Up Again? Real Talk on Dating Disappointments, Blind Dates & Building ConfidenceShow Notes:Why do people keep getting stood up on dates? Gracie and Tracy break down the stats, share real listener stories, and offer practical advice for handling rejection and disappointment in the dating world.Blind dates in 2025: Are they still a thing? The hosts discuss the anxiety of not knowing what your date looks like, how to handle awkward first impressions, and why short, low-pressure first dates are the way to go.Special segment: Navigating dating with ADHD and social anxiety. Listener Jack from England shares his experience, and Gracie and Tracy provide mindset shifts and actionable tips for building confidence and social skills.Launch announcement: The Self-Made Man Dating Journal is now available! Learn how this tool can help you track your dating experiences, reflect, and grow.Listener Q&A: How to avoid getting cynical, set healthy standards, and know when to walk away.Plus: The importance of self-awareness, communication, and not taking rejection personally.Links Mentioned:Self-Made Man Dating Journal - https://www.amazon.com/dp/B0F9B7M5B3?th=1Follow Gracie on Instagram and TikTok: @datingwithgracieEpisode Description:Ever been stood up and wondered, “Is it me, or is this just modern dating?” In this episode, Gracie and Tracy get real about dating disappointments, blind dates, and the mindset shifts that can help you bounce back stronger. They answer listener questions about being stood up, navigating first-date nerves, and dating with ADHD or social anxiety. Plus, they announce the launch of the Self-Made Man Dating Journal—a must-have for anyone serious about improving their dating life.Tune in for honest advice, practical tips, and a reminder that you’re not alone in the dating game. Whether you’re tired of ghosting, anxious about blind dates, or just want to build more confidence, this episode is for you!New episodes every Wednesday. Don’t forget to rate, review, and share!
Episode 42 – Real Stories, Real Advice: Overcoming Dating StrugglesIn this episode of Just Ask Her, dating expert Gracie Pleschourt and certified life coach Tracy Pleschourt tackle real listener questions about the challenges men face in modern dating.You’ll hear three honest stories:Jacob, a dedicated teacher who feels invisible in the dating world, gets advice on shifting his mindset, leveraging his network, and building confidence through daily habits.Nick, a single dad and school administrator, opens up about the struggle to find lasting love and the impact of first-date hookups. Gracie and Tracy break down the importance of pacing, setting standards, and running a “dating experiment” to find deeper connections.Anonymous shares the pain of being friend-zoned and dealing with height insecurity. The hosts offer practical tips for setting boundaries, moving forward, and reframing self-doubt.Plus, discover the new Self-Made Man Dating Journal—designed to help you track your progress, reflect on your experiences, and become more intentional in your dating life.If you’re ready to take control of your dating journey, this episode is packed with actionable advice, mindset shifts, and encouragement. Don’t forget to rate the show, share it with friends, and follow Gracie on Instagram and TikTok @datingwithgracie for daily tips!Resources mentioned:[Self-Made Man Dating Journal – Available on Amazon]Free guide to optimizing your dating profile at datingwithgracie.comNew episodes every Wednesday. No matter where you are or what your situation is—just ask her!
Episode 41 – Flirting, Ghosting, and Setting Standards: Real Dating Advice for MenIn this episode of Just Ask Her, dating expert Gracie Pleschourt and certified life coach Tracy Pleschourt tackle some of the most vulnerable and confusing moments in modern dating. They answer real listener questions about:How to show romantic interest without falling back into toxic masculinity or getting stuck in the “friend zone”What to do when you’re ghosted after a promising connection—and how to separate facts from painful stories your mind createsWhy chemistry isn’t always enough, and how to set and hold your dating standards even when things don’t work outGracie and Tracy share research-backed flirting tips, advice for building confidence, and practical strategies for moving on after rejection. They also discuss the launch of the Self-Made Man Dating Journal, designed to help single men reflect, grow, and date with intention.Whether you’re struggling to make the leap from friendship to romance, reeling from a sudden ghosting, or just want to date with more clarity and confidence, this episode is packed with honest insights and actionable advice.Mentioned in this episode:The Self-Made Man Dating Journal (now available on Amazon)How to use self-compassion to recover from rejectionThe importance of being direct, setting boundaries, and choosing yourself firstIf you enjoy the show, please rate us on Spotify or Apple Podcasts and share this episode with your friends!Follow Gracie on Instagram and TikTok @datingwithgracie for more tips and updates.New episodes every Wednesday. No matter where you are or what your situation is—just ask her.
Episode 40: How to deal, think about and learn from rejection, and what to do nowWelcome back to Just Ask Her, the no-BS podcast for real dating advice straight from a woman’s point of view! In this milestone 40th episode, dating expert Gracie Pleschourt and certified life coach Tracy Pleschourt tackle your toughest questions about moving on, healing, and dating with confidence after heartbreak.In this episode:Submission 1 (Chris, 32, UK Firefighter):Chris finds himself repeatedly attracting women who are fresh out of relationships and struggling emotionally. Gracie and Tracy break down the “rescuer” dynamic, discuss the difference between chemistry and true connection, and offer practical steps for setting dating standards, recognizing patterns, and staying in the “chooser” role.Submission 2 (Anonymous, 27, Med Student):After a nine-year relationship, Anonymous is back in the dating world and wonders if a recent date didn’t work out due to timing or lack of interest. The hosts share how to separate facts from stories, process rejection, and keep moving forward without waiting for a “maybe.”Submission 3 (Matthew, 28, Law Student):Matthew is healing from a recent breakup and wants advice on both moving on and planning a new date. Gracie and Tracy discuss the importance of not waiting until you “feel ready,” making decisions ahead of time, and taking small, confident steps forward.Special Segment:The Self-Made Man Dating Journal is now available on Amazon! Gracie and Tracy introduce their new journal designed to help single men track their dating experiences, reflect, and grow with intention. Limited first run—grab yours before they’re gone! (Link in show notes)Key Takeaways:Don’t let past experiences define your worth or what you deserve.Set clear dating standards and stay in the chooser role.Rejection is a normal part of dating—use it as a learning opportunity.Healing is an active process; don’t wait for closure to move forward.Take small, actionable steps to rebuild confidence and momentum.Resources & Links:Self-Made Man Dating Journal on Amazon https://www.amazon.com/dp/B0F9B7M5B3?th=1Follow Gracie on Instagram and TikTok: @datingwithgracieIf you enjoyed this episode, please rate us on Spotify or Apple Podcasts and share with your friends! New episodes drop every Wednesday.No matter where you are or what your situation is—just ask her.
Episode 39: Dating After Divorce, Overcoming Insecurities & Navigating Workplace RomanceIn this episode of Just Ask Her, dating expert Gracie Pleschourt and certified life coach Tracy Pleschourt answer real listener questions about the challenges men face in modern dating.Topics Covered:Dating After Divorce: Daniel, a recently divorced dad living in the Caribbean, asks how to navigate dating with kids, a limited dating pool, and emotional healing. Gracie and Tracy discuss emotional availability, redefining relationship goals, and the importance of self-awareness.Overcoming Insecurities (Height): Lucas from Canada shares his struggles with dating as a shorter man and feeling stuck in the friend zone. The hosts offer practical tips for building confidence, expressing romantic interest, and leveraging your unique strengths.Workplace Romance: Shane wants to know how to tell if a coworker is interested or just being friendly, and whether it’s appropriate to ask her out again. The conversation covers reading signals, respecting boundaries, and balancing professionalism with personal interest.Bonus: Gracie introduces the Self-Made Man Dating Journal, designed to help men track their dating experiences and grow in self-awareness.Key Takeaways:Emotional readiness and bandwidth are different—define what you want in this season of life.Confidence comes from action and self-acceptance, not just external validation.Flirting and expressing interest can be learned skills—start with small, bold steps.Workplace relationships require extra care and respect for boundaries.Resources Mentioned:Self-Made Man Dating Journal on AmazonFree guides on dating apps, starting conversations, and building chemistry at www.datingwithgracie.comConnect with Gracie:Instagram & TikTok: @datingwithgracieIf you enjoyed this episode, please rate and review on Spotify or Apple Podcasts, and share with friends!
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 – IntroductionGracie and Tracy welcome listeners and celebrate 38 weeks of the podcast.Quick banter about pregnancy timelines and podcast milestones.02:00 – Listener Submission #1: Anthony’s StoryAnthony shares his experience of being publicly shamed in a women’s Facebook group after a breakup.Gracie and Tracy discuss the origins and current state of “Are We Dating the Same Guy?” groups.Advice on handling online defamation, reclaiming self-trust, and whether to pursue legal action.Key takeaway: Let your integrity and self-awareness guide you, and don’t let drama-filled groups define your dating future.25:00 – Announcement: Self-Made Man Dating JournalGracie and Tracy introduce their new journal for single men, available on Amazon.The journal helps track dates, reflect on experiences, and build self-awareness.28:00 – Listener Submission #2: Alex’s StoryAlex, new to dating, wonders if he missed his chance with a neighbor after helping her through a tough time.The hosts discuss the importance of momentum, meaningful interactions, and not overthinking timing.Advice: Focus on genuine conversations, set healthy boundaries, and don’t attach expectations to every interaction.40:00 – Listener Submission #3: Jake’s StoryJake describes a fast-moving, long-distance romance that ended suddenly after a deep connection.Gracie and Tracy explain “emotional fast-tracking” and the risks of future-tripping in new relationships.Advice: Let relationships unfold at a natural pace, integrate emotional lessons, and practice patience as you move forward.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 JournalGet Gracie’s Free Guides at: 👉https://datingwithgracie.com/Check out the Dating With Gracie Community at: 👉⁠https://www.skool.com/dating/about⁠Want to be featured on the podcast? Submit your story & question: 👉  "Just Ask Her" Podcast SubmissionFollow 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: @‌datingwithgracieNew 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 JournalGet Gracie’s Free Guides at: 👉https://datingwithgracie.com/Check out the Dating With Gracie Community at: 👉⁠https://www.skool.com/dating/about⁠Want to be featured on the podcast? Submit your story & question: 👉  "Just Ask Her" Podcast SubmissionFollow 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 availabilityHow to start conversations that actually connectThe over-functioning pattern that leaves good men feeling unseenBuilding confidence without performingWhen to try again—and when to walk away for goodWhether 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 JournalGet Gracie’s Free Guides at: 👉https://datingwithgracie.com/Check out the Dating With Gracie Community at: 👉⁠https://www.skool.com/dating/about⁠Want to be featured on the podcast? Submit your story & question: 👉  "Just Ask Her" Podcast SubmissionFollow for more honest, no-fluff dating advice: 📲 ⁠Instagram⁠ | ⁠TikTok⁠ | ⁠YouTube⁠If 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 contactThe truth about mixed signals and sudden disappearancesWhy “perfect dates” don’t always lead to commitmentHow to rebuild your confidence after being ghostedWhen (and how) to reach out again—or let go completelyWhether 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=1Get Gracie’s Free Guides at: 👉https://datingwithgracie.com/Check out the Dating With Gracie Community at: 👉⁠https://www.skool.com/dating/about⁠Want to be featured on the podcast? Submit your story & question: 👉  "Just Ask Her" Podcast SubmissionFollow for more honest, no-fluff dating advice: 📲 ⁠Instagram⁠ | ⁠TikTok⁠ | ⁠YouTube⁠
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