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 right—and she still chooses someone else
✅ Dating after divorce with zero experience: how to rebuild confidence with women
✅ How to talk to women you’re into (especially when you're not sure if you're moving too fast)
✅ Whether it's ever okay to reach back out after you’ve been rejected
✅ Why defining the relationship early on doesn’t have to be awkward or needy

We also offer specific, judgment-free dating advice for men navigating emotional setbacks, rebuilding after heartbreak, or figuring out how to connect with women authentically in today’s dating world.

If you’ve been wondering where to meet quality women, how to approach someone new, or when to speak up about your feelings—this episode is for you.

Want support in your dating life?
Join the exclusive Dating With Gracie Membership for single men:
👉 https://www.skool.com/dating/about

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Submit your story & question:
👉 [Submit here]

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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 dating life?
🔸 Does dating really get harder the older you get?

If you’ve ever felt overlooked, used, or unsure how to start again—this one’s for you.

If you want help with your dating life, join the exclusive Dating With Gracie Membership for single men:
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If you'd like a chance to be featured on the pod, fill out a submission below:
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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, friends, or a random real-life moment

If you’re tired of wasting your energy on women who aren’t putting in effort—or sick of being the nice guy who never gets the girl—this one’s for you.

If you'd like help optimizing your dating profile, grab Gracie's FREE guide here:

Free Dating Profile Guide

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, fill out a submission below:⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Submit here

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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 confidence or what to do after the first few dates.

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, fill out a submission below:⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Submit here

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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, 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, fill out a submission below:⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Submit here

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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 you” message hits your phone.

If you want to see the Sea Nymph 3.0, check it out here:

https://youtu.be/aOOHDYXBeOU?si=Iq8L8qZK9siaaQPG

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, fill out a submission below:⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Submit here

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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 in love, questioning your place in a woman’s life, or dealing with mixed emotions around trust and independence—this is your episode.

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, fill out a submission below:⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Submit here

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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/about

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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

If you'd like a chance to be featured on the pod, fill out a submission below:

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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

If you'd like a chance to be featured on the pod, fill out a submission below:

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