Podcast Episode

Does She Like You? You’re Asking the Wrong Question. (Ep.93)

Just Ask Her - Dating Advice for Single Men··19 September 2026·47 min

About this episode

What if uncertainty isn’t the problem with dating? What if learning how to handle it is the skill that changes everything? In this episode of Just Ask Her, Gracie and Tracy tackle three dating dilemmas from men at very different stages of life, all struggling with the same thing: trying to know the outcome before taking the next step. First, a great first date turns into mixed signals, canceled plans, Instagram comments, and silence. Is she genuinely interested or stringing him along? Next, a 49-year-old listener struggling with social anxiety asks how to become more attractive to women. But his real challenge might not be attraction at all. Finally, a 23-year-old wants to turn a college friendship into something more without making things awkward. Should he tell her he’s interested? How much should they text first?  Plus, Gracie shares an incredible dating story involving a bachelorette party, country dancing, a Pitbull costume, a bald cap, a wrong phone number, and some impressive LinkedIn detective work. Whether you’re dealing with mixed signals, dating anxiety, rejection, overthinking, texting, approaching women, asking someone out, building confidence, or figuring out if she likes you, this episode is about getting comfortable with not knowing what happens next. Because dating confidence isn’t knowing she’ll say yes. It’s knowing you’ll be okay with the answer either way. Have a dating dilemma? Submit yours for a chance to be featured on a future episode. Self-Made Man Dating Journal -  https://self-made-u.myshopify.com/products/self-made-man-dating-journal?utm_source=copyToPasteBoard&utm_medium=product-links&utm_content=web Submission Form: https://forms.gle/e7LTvCkT1fhkFQEF8 Join the 30 Day Rizz Challenge at https://www.skool.com/rizz-challenge/about Chapters:00:00 Stop Chasing Certainty01:00 Welcome to Just Ask Her01:31 Baseball & Concerts05:53 The Pitbull Love Story14:30 Submission #1: Mixed Signals16:22 Did He Mess Up?17:41 Is She Stringing Him Along?20:52 Why Mixed Signals Hook You21:50 Are You Missing Her?24:15 Should He Give Her Another Chance?25:24 The Self-Made Man Dating Journal26:34 Submission #2: Fear of Rejection27:35 Attraction vs. Avoidance29:18 Why Asking Women Out Feels Terrifying30:28 Building Social Confidence32:01 Redefining Dating Success33:18 How to Handle Rejection36:25 Stop Waiting for Certainty37:00 Submission #3: Friends to Dating38:52 Should He Ask Her Out?40:25 You’re Not Supposed to Know42:18 Can Friendship Become Romance?43:47 Stop Overthinking Texting45:25 How Much Should You Text?46:34 Final Thoughts #DatingAdvice #DatingAdviceForMen #RelationshipAdvice #DatingConfidence