Just Ask Her - Dating Advice for Single Men

Just Ask Her - Dating Advice for Single 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
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Episode's summary

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 relationships that left him questioning his confidence and self-worth. Now that he's done the work to heal and figure out what he actually wants in a partner, there's a new problem: he freezes around women he's genuinely attracted to. Then things get... weird. Another listener has been dating a woman for FIVE MONTHS. They spend hours together. They go to dinner. They exchange gifts. He's bought her roses. Sounds promising, right? Well... he doesn't know her last name. He doesn't know exactly where she lives. They haven't kissed, held hands, or even really hugged. Oh, and he's afraid asking about any of this might push…

Episodes

98-

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

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 relationships that left him questioning his confidence and self-worth. Now that he's done the work to heal and figure out what he actually wants in a partner, there's a new problem: he freezes around women he's genuinely attracted to. Then things get... weird. Another listener has been dating a woman for FIVE MONTHS. They spend hours together. They go to dinner. They exchange gifts. He's bought her roses. Sounds promising, right? Well... he doesn't know her last name. He doesn't know exactly where she lives. They haven't kissed, held hands, or even really hugged. Oh, and he's afraid asking about any of this might push…

07 Oct 2026
97-

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

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 to figure out whether he actually wants his ex back or just wants the heartbreak to stop. After years of changing himself, chasing connection, and trying to be "enough" for his partner, how does he rebuild his confidence without turning healing into another performance? Then, Jacob is dating a woman who had just gotten out of a relationship days before their first date. The chemistry started strong, but now the texting has slowed down and the energy feels different. Is she emotionally unavailable? Is he becoming the rebound? Should he give her space, walk away, or let her set the pace? Finally, our returning submitter…

30 Sep 2026
96-

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…

23 Sep 2026
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…

16 Sep 2026
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TRUTH or TRASH? We React to Men’s Dating Hot Takes (Ep.1)

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

15 Sep 2026