What happens when Don Lemon gets truly unfiltered?

In this heartfelt, funny, and deeply honest conversation, Don opens up about aging with confidence, coming out in midlife, letting go of old shame, and the freedom that comes from no longer needing anyone’s approval. We talk about identity, love, sex, wisdom, and why his mantra “old people be knowing” captures the real gift of growing older.

Don also reflects on the state of media, the “prime” controversy, and how stepping away from traditional news helped him reclaim his voice and his joy. If you’re ready for truth, evolution, and a warm reminder that life after 50 can get better, tune in. Watch now.

Timestamps:

00:00 Chip’s episode opening

00:57 Don on aging and happiness

02:34 Don’s childhood and early years

03:38 Politics, Reagan, and identity

06:52 Dating while closeted

09:52 College years and social life

12:17 First gay bar experiences

16:20 Don’s coming-out story

19:47 Coming out publically in a book

21:41 Midlife chrysalis and confidence

25:10 What gets better with age

28:28 The “prime” controversy explained

34:07 State of media and independence

36:30 Politics, division, and future outlook

37:26 Don on never retiring

38:49 Possible regret 10 years from now

40:24 Don’s wisdom bumper sticker

43:54 3 Judy Garland and music icons

46:50 Chip’s reflections

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