All Episodes

May 14, 2025 37 mins

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

Want to be featured on the podcast?
Submit your story & question:
👉 [Submit here]

Follow for more honest, no-fluff dating advice:
📲 Instagram | TikTok | YouTube


Mark as Played

Advertise With Us

Popular Podcasts

Bookmarked by Reese's Book Club

Bookmarked by Reese's Book Club

Welcome to Bookmarked by Reese’s Book Club — the podcast where great stories, bold women, and irresistible conversations collide! Hosted by award-winning journalist Danielle Robay, each week new episodes balance thoughtful literary insight with the fervor of buzzy book trends, pop culture and more. Bookmarked brings together celebrities, tastemakers, influencers and authors from Reese's Book Club and beyond to share stories that transcend the page. Pull up a chair. You’re not just listening — you’re part of the conversation.

On Purpose with Jay Shetty

On Purpose with Jay Shetty

I’m Jay Shetty host of On Purpose the worlds #1 Mental Health podcast and I’m so grateful you found us. I started this podcast 5 years ago to invite you into conversations and workshops that are designed to help make you happier, healthier and more healed. I believe that when you (yes you) feel seen, heard and understood you’re able to deal with relationship struggles, work challenges and life’s ups and downs with more ease and grace. I interview experts, celebrities, thought leaders and athletes so that we can grow our mindset, build better habits and uncover a side of them we’ve never seen before. New episodes every Monday and Friday. Your support means the world to me and I don’t take it for granted — click the follow button and leave a review to help us spread the love with On Purpose. I can’t wait for you to listen to your first or 500th episode!

Dateline NBC

Dateline NBC

Current and classic episodes, featuring compelling true-crime mysteries, powerful documentaries and in-depth investigations. Follow now to get the latest episodes of Dateline NBC completely free, or subscribe to Dateline Premium for ad-free listening and exclusive bonus content: DatelinePremium.com

Music, radio and podcasts, all free. Listen online or download the iHeart App.

Connect

© 2025 iHeartMedia, Inc.