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PODCAST

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

society & culture relationships

All Episodes

00:42:11

Dating After 35, First Dates at 62 & Grieving Love:...

Just Ask Her - Dating Advice for Single Men ·

2025/06/18

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 experienceThe challenges of dating in your 60s and getting past the first dateWhether it’s fair to pursue someone who’s still grievingWhy your dating history matters less than your emotional readinessHow to show

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00:52:00

When the Vibes Are There… But She Isn’t: Mixed...

Just Ask Her - Dating Advice for Single Men ·

2025/06/11

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 wellHow to read and respond to mixed signals from someone who says they want something casual but keeps acting

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00:34:03

Navigating Summer Sparks, Career Focused Dating, and...

Just Ask Her - Dating Advice for Single Men ·

2025/06/04

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 social life are unattractive to potential partners. Finally, they address

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00:33:54

Dating in Small Towns, Big Cities & Emotional Limbo:...

Just Ask Her - Dating Advice for Single Men ·

2025/05/28

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 possibleWhy big city dating often feels like one big performanceWhether moving for love is a smart idea—or a sneaky form of self-abandonmentWhat to do when your dating

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00:43:45

How to Stop Being the ‘Safe Guy’ and Start Being Seen...

Just Ask Her - Dating Advice for Single Men ·

2025/05/21

EP 26 — Timing, Betrayal, and the Friend Zone: Real Advice for Modern DatingIn 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 seen as a romantic option.🚩 A man reconnects with a woman from his

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00:37:54

Dating Advice for Men Who Feel Out of Practice, Out...

Just Ask Her - Dating Advice for Single Men ·

2025/05/14

Episode 25 – Dating Advice for Men Feeling Out of Practice, Out of Options, or Unsure Where They StandIn 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 right—and she still chooses someone else✅ Dating after divorce with zero

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00:38:30

Feeling Like You’re Behind in Dating? Here’s What to...

Just Ask Her - Dating Advice for Single Men ·

2025/05/07

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 down this week’s polls:🔸 Do you ever feel like you’re behind in your

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00:37:08

Is Being Too Nice Costing You Dates? (Ep #23)

Just Ask Her - Dating Advice for Single Men ·

2025/04/30

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 at texting”🔸 Whether guys still want to meet someone through apps,

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00:51:03

Ep 22: Nice Guys, Situationships & Starting Over

Just Ask Her - Dating Advice for Single Men ·

2025/04/23

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 who's done being the “nice guy,” but isn’t sure how to date with

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00:46:04

Ep 21: When You’re Doing Everything Right—But Still...

Just Ask Her - Dating Advice for Single Men ·

2025/04/16

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 who doesn’t believe in labels.If you want help with your dating life,

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01:04:14

Ep 20: Is It Even Worth Dating Right Now?

Just Ask Her - Dating Advice for Single Men ·

2025/04/09

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, if a birthday text is a bad idea, and what to do when that “I miss

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01:11:54

Ep 19: She’s Grabbing Dinner with Her Ex… What Do I Do?

Just Ask Her - Dating Advice for Single Men ·

2025/04/02

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 secretly don’t love. 👀If you’ve ever struggled with feeling behind

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00:46:41

Ep 18: Why It Keeps Ending After 3 Dates (And How to...

Just Ask Her - Dating Advice for Single Men ·

2025/03/26

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:⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.skool.com/dating/about⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠If you'd like a

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01:07:20

Ep 17: She Checks All the Boxes—So Why Don’t I Feel It?

Just Ask Her - Dating Advice for Single Men ·

2025/03/19

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/about⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠If you'd like a chance to be featured on the pod, fill out a

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01:08:08

Ep 16: Does She Like You Or Just Want a Free Drink?

Just Ask Her - Dating Advice for Single Men ·

2025/03/12

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/about⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠If you'd like a chance to be featured on the pod, fill out a

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00:59:54

Ep 15: Is There Such a Thing as 'The Right Person,...

Just Ask Her - Dating Advice for Single Men ·

2025/03/05

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 Dating With Gracie Membership for single

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00:43:49

Ep 14: How to Have a Shot With Younger Women

Just Ask Her - Dating Advice for Single Men ·

2025/02/26

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/about⁠⁠⁠⁠⁠⁠⁠⁠⁠If you'd like a chance to be featured on the pod, fill out a submission

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01:04:14

Ep 13: Dating Multiple Women at Once

Just Ask Her - Dating Advice for Single Men ·

2025/02/19

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/about⁠⁠⁠⁠⁠⁠⁠⁠If you'd like a chance to be featured on the pod, fill out a submission below:⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Submit here⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Follow For

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00:51:31

Ep 12: How to Leverage Being Single on Valentine's Day

Just Ask Her - Dating Advice for Single Men ·

2025/02/11

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/masterclass⁠If you want help with your dating life, join the exclusive Dating With Gracie Membership for single

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00:56:17

Ep 11: Work Crushes, Exes, and Valentine’s Day...

Just Ask Her - Dating Advice for Single Men ·

2025/02/05

In this episode of 'Just Ask Her,' dating experts Gracie and Tracy Pleschourt discuss navigating feelings for a close friend at work and reconnecting with an ex. Gracie announces a special free live Valentine's Day masterclass on attracting your dream girl. They analyze listener submissions, offering advice on expressing feelings to a recently single friend and the complexities of rekindling past relationships. The episode concludes with engaging polls about dating profiles and first

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