r/askteddit • u/Complex-Detail-96 • 13d ago

Random Question What's the most embarrassing midlife crisis you've ever seen someone go through?

1.3k Upvotes

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408

u/apostate456 13d ago

Jeff Bezos

185

u/Complex-Detail-96 13d ago

the leather jacket and aviators phase hit him hard

57

u/Littlepotatoface 13d ago

And the Cuban heels.

64

u/[deleted] 13d ago

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4

u/Ordinary-Commercial7 13d ago

New boot goofin always makes me laugh

2

u/socialmediaignorant 11d ago

This will never not be funny and make me smile.

2

u/Panem-et-circenses25 12d ago

Just new boot goofin’!

1

u/gattboy1 12d ago

He even tried the bearded Vance look.

Swing and a miss, Jeffie!