289: How To Overcome Your Biggest Dating Insecurities

Love Life with Matthew Hussey

Matthew Hussey

Relationships, Society & Culture

4.8 • 2.9K Ratings

🗓️ 26 March 2025

⏱️ 77 minutes

🔗️ Recording | iTunes | RSS

🧾️ Download transcript

Summary

In this episode, we dive deep into the biggest challenges people face in dating — from rejection and insecurity to feeling like the odds are stacked against you.

Whether you feel stuck due to age, lack of experience, body image, or financial worries, this episode is packed with reframes, real-life listener questions, and practical mindset shifts to help you get out of your own way and start moving forward with confidence.

PLUS: A special interview with Lewis Howes on handling overwhelm, emotional regulation, and why taking imperfect action is the key to growth in both life and love.

✨ Main topics covered:

How to reframe limiting stories that are holding you back in dating
Dating with insecurities around age, experience, weight, or finances
Listener questions answered with real advice for building confidence
How to stop pre-rejecting yourself and “take yes for an answer”
Lewis Howes on emotional regulation, handling pressure, and showing up without perfection
Fun “Instant Reframe” segment to turn common dating obstacles into positives

👉 Want help reframing what’s holding you back? Ask Matthew AI here: Askmh.com

🎟️ Grab your early bird tickets for the MH Retreat here: MHRetreat.com

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📩 Got a question or feedback? Email us at: [email protected]

🎧 Subscribe for more weekly episodes and practical dating advice!

Transcript

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0:00.0	Matthew.
0:05.0	Stephen.
0:06.0	We've been very quiet this year, I would say, so far.
0:09.0	Haven't left the house much.
0:10.0	We've been very much bunkered.
0:12.0	Not a word.
0:13.0	Bunkered?
0:14.0	Bunkered and hunkered.
0:16.0	Very strange phrase, but go on.
0:18.0	We've been bunkered and hunkered at home because we've been our heads down working,
0:21.2	staying in L.A. I'm wondering if we have any fun trips coming up, Matthew. Could you be talking
0:26.3	about a little trip we're doing in October? Oh, is it October? Where's that? Oh, it's in Miami, Stephen.
0:32.2	Have you forgotten? I think you're talking about the Matthew Hussie Retreat. Now the two-day version of the Matthew-Hassie
0:38.4	Retrie. First time ever, Stephen. Used to be six days. Now it's too. Much easier to come to
0:43.2	than ever. More affordable. Travels easier. Less time off work. You can come. You can change
0:49.6	your life in two days and get the hell out. Okay. And am I going to work on my core confidence of that retreat?
0:54.6	You will have a better relationship with yourself by the end of it, yes.
0:57.4	Am I going to deal with my unhealthy patterns and habits?
1:00.3	There will be patterns that you've had your whole life that you've struggled to overcome.
1:04.2	Fatal flaws, dare I say, that you will be able to finally shift, yes.
1:09.6	Okay.
1:10.1	And I'm a man.
	...

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