Imagine being 17, renting your tux, getting a haircut, shaving your weird little mustache, and then getting punked out by Shaun freaking White.

Kylie Jenner CRACKED.COM In 2017, this dude put up flyers looking for a date after his elaborate promposal was rejected. Jenner's staff saw one, got her in touch, and made him the most popular guy in school.

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Brandy CRACKED.COM Kobe was already on the cusp of being rich and famous when he met Brandy at the Essence Awards. But he was still a shy 17-year-old just trying to survive finals, SO naturally, he waited a few weeks and had a friend ask her to prom.

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