Just Ask Her - Dating Advice for Single Men

What does it really take to start over in dating—whether you’re 36, 62, or healing from deep emotional loss? In this episode of Just Ask Her, we respond to three powerful submissions from men navigating dating later in life.

We talk about:

• How to date after a bipolar diagnosis and little-to-no experience

• The challenges of dating in your 60s and getting past the first date

• Whether it’s fair to pursue someone who’s still grieving

• Why ...

Why do some of your best dates go absolutely nowhere? In Episode 29 of Just Ask Her, Gracie and Tracy break down the most frustrating moments in modern dating—from ghosting after great chemistry to navigating the mixed signals that leave you stuck in limbo.

We answer three listener questions that highlight common (but painful) scenarios:

• Why women disappear after everything seems to be going well

• How to read and respond to mixed s...

In this episode of 'Just Ask Her,' hosts Gracie Pleschourt, a dating expert, and her co-host Tracy Pleschourt, a certified life coach, tackle three insightful submissions from male listeners facing distinct dating challenges. They begin with JJ, a college student wondering how to keep a new spark alive over a three-month summer break. Next, they advise Mike, a 30-year-old trauma survivor worried if his career focus and limited soci...

In this episode of Just Ask Her, Gracie and Tracy tackle three powerful submissions from men feeling stuck—whether it’s bumping into your ex at the gym, navigating emotionally messy flings in big-city bars, or wondering if your small town is what’s keeping you single.

You'll hear:

• How to protect your peace when “no contact” isn’t possible

• Why big city dating often feels like one big performance

• Whether moving for love is a smar...

EP 26 — Timing, Betrayal, and the Friend Zone: Real Advice for Modern Dating

In this episode of Just Ask Her, Gracie and Tracy tackle three brutally honest listener submissions from men navigating complex, emotional dating challenges:

🩺 A cancer survivor steps into the dating world for the first time—only to kiss a woman who turns out to be married.
🧸 A self-described “safe guy” keeps getting friend-zoned and wants to know how to be...

Episode 25 – Dating Advice for Men Feeling Out of Practice, Out of Options, or Unsure Where They Stand

In this episode of Just Ask Her, Gracie and Tracy respond to three real and relatable listener stories that highlight what so many men are quietly struggling with—feeling behind in dating, unsure how to make a move, or completely lost on what women actually want.

Here’s what we cover:

✅ When you feel like you're doing everything righ...

This week, Gracie and Tracy respond to three real submissions from men who feel like they’re doing everything right—but still struggling in their dating lives.

They talk about what to do when you’re successful on paper but can’t seem to meet women your age, how to recover after giving too much to someone who took advantage of you, and how to date confidently when you feel like a “late bloomer” who’s already behind.

They also break do...

This week, Gracie and Tracy respond to two submissions that hit on a common frustration: putting in effort and still not getting the outcome you want.

They talk about what to do when you keep hearing you're “too sweet” or “a great guy” but still get rejected—and how to handle it when every conversation with a woman feels like a dead end.

They also break down this week’s polls:
🔸 What it really means when a girl says “I’m bad ...

This week, Gracie and Tracy cover everything from confusing situationships to rebuilding your confidence after divorce.

They unpack how to handle it when she says you're just friends but keeps hooking up with you, whether it's time to give an ultimatum to a girl who's still living with her boyfriend, and how to stop feeling lost when it seems like you don’t belong anywhere.

They also offer guidance to a newly divorced dad...

This week, Gracie and Tracy talk about what happens when focusing on self-growth starts to make dating feel… unnecessary, how to handle it when women change your date plans (and whether that’s a secret test), and the pros and cons of dating someone who’s connected to your family through past relationships.

Plus, they react to your votes on this week’s polls—like the most confusing part of dating and whether you'd be open to someone ...

This week, Gracie and Tracy dive into three listener submissions.

They talk about what dating feels like after divorce and years off the market, how to handle it when your proposal gets rejected and you're unsure where the relationship stands, and whether it’s worth putting yourself out there when you’re still working on your weight loss goals.

They also react to this week’s poll results on exes—like whether you should be friends...

This week, Gracie and Tracy dive into listener submissions that include: what to do when you feel stuck and scared you’ll never find someone, how to handle your girlfriend grabbing dinner with her ex, and adjusting to dating an ultra-independent woman when you’re used to being the caretaker in the relationship.

They also react to your responses to this week’s polls—including top fears in dating and a list of what women wear that men...

This week, Gracie and Tracy are back from Utah and diving into three relatable listener submissions: how to stop sabotaging early dating stages, why you’re not getting texts back after meeting women on a night out, and whether it’s ever a good idea to try and reach back out to a girl you ended things with in the past.

If you want help with your dating life, join the exclusive Dating With Gracie Membership for single men:⁠⁠⁠⁠⁠⁠⁠⁠...

In this episode of Just Ask Her, Gracie and Tracy tackle some of the toughest dating dilemmas men face—choosing between chemistry and compatibility, navigating feelings for a friend, and decoding mixed signals from a woman who “has love” for you but doesn’t want a relationship.

If you want help with your dating life, join the exclusive Dating With Gracie Membership for single men:

⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.skool.com/dating/about⁠⁠⁠...

This week Gracie and Tracy dive into the complexities of workplace romances, strategies for avoiding being used for free drinks, whether men should be honest about their height on dating profiles, and how to deal with an ex who moves on quickly but still remains in contact. 

If you want help with your dating life, join the exclusive Dating With Gracie Membership for single men:

⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.skool.com/dating/about⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

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In this episode of 'Just Ask Her,' Gracie and Tracy address how to handle feeling exhausted from past relationships, setting and maintaining boundaries when someone doesn't share your romantic interest, and the complexities of workplace crushes. They also discuss audience polls about 'right person, wrong time' and attitudes towards dating women who earn significantly more.

If you want help with your dating life, join the exclusive ...

This week Tracy and Gracie kick off the episode with their opposing opinions on the popular dating show, Love Is Blind. The topics covered include the chances of rekindling after being rejected, dating age gaps, and dating women who have complicated personal lives.

If you want help with your dating life, join the exclusive Dating With Gracie Membership for single men:

⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.skool.com/dating/about⁠⁠⁠⁠⁠⁠⁠⁠⁠

If yo...

This week Tracy and Gracie read the first ever update from a previous submission! They also touch on themes such as navigating long-distance connections, handling insecurities, and dating multiple people respectfully.

If you want help with your dating life, join the exclusive Dating With Gracie Membership for single men:

⁠⁠⁠⁠⁠⁠⁠⁠https://www.skool.com/dating/about⁠⁠⁠⁠⁠⁠⁠⁠

If you'd like a chance to be featured on the pod, fi...

In this week's episode Gracie and Tracy provide advice to single men on navigating Valentine's Day. The episode covers everything from leveraging the day to meet single women, planning special, yet not over-the-top dates, and avoiding common Valentine's Day pitfalls.

Valentine's Day Masterclass Sign up (Feb 14th, 2025):

⁠https://datingwithgracie.com/masterclass⁠

If you want help with your dating life, join the exclusive Dating With Gr...