289: How To Overcome Your Biggest Dating Insecurities

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

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

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