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

Episodes

November 5, 2025 26 mins

Episode 50: Real Dating Questions Answered – Confidence, Signals & Starting Over

Description:
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 strai...

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Episode 49: Ghosted, Blocked, and Bouncing Back — Real Dating Dilemmas & Self-Made Man Advice

Episode 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...

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Dating After Divorce – Confidence, Apps & Real Connections for Men Over 40 Ep. 48

Hosts: Gracie Pleschourt & Tracy Pleschourt

In This Episode:

  • [00:00] Welcome & Introduction

  • [01:30] Listener Question: Starting Over After Divorce at 45

    • Breaking old routines and building new momentum

    • Is there a “market” for divorced men over 40?

    • How to meet new women and rebuild your social circle

    • The fastest-growing demographic on dati...

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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 yo...

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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 instead

  • The m...

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Break the Cycle: Real Advice for Dating Confidence, Moving On, and Finding Love
Episode 45 – Just Ask Her Podcast

Episode 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 t...

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Episode 44: Living at Home, Gym Love, and Mixed Signals

Hosts: Gracie Pleschourt & Tracy Pleschourt

Struggling 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 s...

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Episode 43: Stood Up Again? Real Talk on Dating Disappointments, Blind Dates & Building Confidence

Show 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...
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Episode 42 – Real Stories, Real Advice: Overcoming Dating Struggles

In 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 conf...
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Episode 41 – Flirting, Ghosting, and Setting Standards: Real Dating Advice for Men

In 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 whe...
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Episode 40: How to deal, think about and learn from rejection, and what to do now

Welcome 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 (C...

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Episode 39: Dating After Divorce, Overcoming Insecurities & Navigating Workplace Romance

In 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...
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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 a...

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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:

  1. Dakota’s Dilemma:
    A 31-year-old en...

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  • 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...

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    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 cla...

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    She said she only wanted something casual… but your heart didn’t get the memo.

    In this episode of Just Ask Her, we’re diving into three real stories that hit home for a lot of men:

    • A 36-year-old man rekindles something with the woman who once ghosted him—only to find himself falling all over again. Is she just bored… or is there still a chance?

    • Another listener goes from intimate and honest connection to total silence after dating...

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    This week on Just Ask Her, we’re tackling three very real (and wildly different) dating dilemmas from our listeners:

    • Carlos wants to know if there’s any hope for a conservative guy dating in a liberal city—or if he should hold out for a future move.

    • Mark has rekindled things with his high school sweetheart… but there’s one big problem: she’s still best friends with his ex-wife.

    • And an anonymous bachelor is wondering how to strike ...

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    In today’s episode, we’re diving into three powerful stories from men navigating the messy middle of modern dating:

    💔 Luke thought he was one step away from proposing—until she blindsided him with a breakup.
    😓 Josh is tired of being the one who always initiates, and he’s starting to feel the desperation creeping in.
    🥲 Jerome had the best first date of his life… but now she’s gone quiet, and he’s left wondering if he should ...

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    In Episode 31 of Just Ask Her, we dive into one of the most confusing dating experiences: when everything starts fast, feels promising… and then suddenly falls apart. From whirlwind reconnections to mixed signals after first dates, these listener stories are full of emotional highs, unexpected letdowns, and hard-earned lessons.

    Evan shares what it’s like to be pulled in deeply—then pushed away after one perfect weekend. AL wonders i...

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