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Strictly Anonymous Confessions

1493 - John Lost His Virginity at 23 and Hasn't Had Sex Again in 14 Years?!

6/19/20261 hr 15 min

John  lost his virginity at 23 and hasn't had sex again in fourteen years and he called in to talk all about it. Tune in to hear how he lost his virginity to a woman nearly 20 years older than him, why their brief relationship ended and why he hasn't had sex with anyone else since, ow his upbringing may have contributed to his commitment issues, why he's convinced the worst-case scenario will always happen, how his overthinking and avoidance have held him back for over a decade, the women he's dated since and why none of those relationships ever progressed, why he's terrified of rejection, the coworker he likes now but has never made a move on, what he really wants from a relationship,  advice he can use to finally get out of his own way and start dating again plus a whole lot more.

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Clips

You're A 40-Year-Old Virgin
Watch Real-Time Oral Sex Lessons
Nobody Actually Cares That Much
Life's Too Short—Start Living
Love Outweighs Loss, Even Dogs

Transcript preview

First 90 seconds

  1. Speaker 10:00

    On June 26th, Supergirl arrives in theaters Let's go.

  2. Kathy· Host0:03

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  3. Speaker 40:06

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  6. Speaker 20:13

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  7. Speaker 10:16

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  8. Speaker 50:20

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  9. Speaker 20:21

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  10. Speaker 50:22

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  11. Speaker 10:23

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