Just Ask Her - Dating Advice for Single Men

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 conne...

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 b...

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’...

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 af...

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 pur...

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...

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 i...

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 performan...

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 f...

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 yo...

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...

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 reall...

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 o...

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 a...

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 ex...

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 an...

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 Me...

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: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠htt...

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://...

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 yo...

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.co...

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...

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 l...

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 reki...

In this episode of 'Just Ask Her,' Gracie and Tracy Pleschourt address how financial stability impacts dating, offer advice on first interactions and date conversations, and provide insight into processing sudden relationship shifts. They also explore effective ways to approach women and evaluate the importance of standards in dating. Join the discussion for practical guidance on improving your da...