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.

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.

Source: E

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