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June 17, 2025 65 mins

Today's podcast episode is a coaching session with Michelle. She's in her 50s, divorced after a 24-year marriage, and getting back into dating after being with one person her whole adult life.

In this raw and powerful coaching session, we unpack the overwhelm of dating apps, the anxiety of being “naive,” and the pressure late bloomers feel to already know how dating is supposed to work.

Michelle shares how:

→ Dating apps make her feel panicked in 3 minutes or less

→ She’s afraid she missed the memo on how to flirt or date

→ All she really wants is a partner to laugh with at a family campsite, but dating feels like an IMPOSSIBLE way to get there.

We talk about self-compassion, letting go of judgment, and what it means to stop settling—not just for the wrong relationship, but for a miserable dating life.

 

📺 Or watch the video version on YouTube! (@datebrazen)

 

Work with Lily:

🔗 Free Live Training on June 17th: datebrazen.com/lets-go

🔗 Learn about Main Character Dating: datebrazen.com/waitlist

🔗 Book: Thank You More Please

🔗 YouTube Channel

🔗 TikTok

🔗 Instagram

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