Episode
51

The 4 Dating Mistakes Keeping Smart Women Stuck (And How to Break Them)

with
Tamsen Fadal
New episodes every week

Episode Description

Tamsen Fadal sits down and teaches you what she’s learned about dating, from running a matchmaking business in New York City, to dating through her 20s and 30s, to divorce, and starting over in midlife.

In this episode, she walks you through the 4 biggest dating mistakes women make. The ones that keep smart, self-aware women repeating the same patterns, settling, or wondering why they keep dating the wrong men.

This is about understanding why these mistakes happen and walking away with tools to stop repeating them.

What you’ll learn

  • Why dating for validation feels tempting and how to shift toward real connection
  • How timelines and panic dating push you to ignore red flags
  • Why dating someone’s potential keeps you stuck and what to look for instead
  • How women slowly disappear in relationships and how to stay fully yourself

By the end of this episode you’ll see dating with more clarity, more self-trust, and more emotional safety. You’ll have a clearer sense of what’s been holding you back and how to start choosing relationships that actually support who you are.

Timestamps

0:00 Intro

01:16 Tamsen's Dating History and the Patterns She Had to Face

03:11 Mistake #1: Dating for Validation Instead of Connection

04:29 Non-Negotiables, Checking In, and Flipping the Question

6:10 Mistake #2: Dating With a Timeline Instead of Trust

7:50 Replacing the Dating Timeline With a Compass

12:23 Mistake #4: Dating Someone’s Potential Instead of Reality

14:20 Breaking the Pattern with the Forever Question

17:34 Mistake #4: Losing Yourself in a Relationship

18:45 3 Ways to Maintain Your Identity in a Relationship

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guest appearing in this episode

Tamsen Fadal

Tamsen Fadal sits down and teaches you what she’s learned about dating, from running a matchmaking business in New York City, to dating through her 20s and 30s, to divorce, and starting over in midlife.

Other related resources

Your 2026 Dating Profile Cheat Sheet free guide by Tamsen Fadal with dating expert Bela Gandhi

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Get the FREE 2026 Dating Profile Cheat Sheet I made with dating expert Bela Gandhi, with the mindset, photos and bio tips to help you show up as you.

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medical disclaimer:

The information provided in this podcast is for educational and informational purposes only and is not intended as medical advice. Always consult with a qualified healthcare professional regarding any medical concerns or treatment options. The views expressed by guests are their own and do not necessarily reflect those of The Tamsen Show.