Probably our best submission yet. And by that I mean our worst. Everyone is always sending in shots of their buddies in Halloween costumes and shit. That’s not how they really dress. This is Coop in all his normal day to day life, dressed like a homeless 7th grader.

Time to reload the Miltons machine. Send all sob stories to pimpmylook@barstoolsports.com or pimpmydate@barstoolsports.com and help us help you. And you need to send pictures! If you sent an email without a picture resend with one to be considered.

Today’s Contestant

Reader Email

Pres,

Our friend Coop has never talked to a girl in his life, one reason is his clothing. He owns three shirts and two of them are bruins shirts and the other one is Tommy Bahama. If you could help him out, he might actually be able to gain the confidence to talk to some girls, it’s up to you prez. Please help our clueless and lost friend out.Your his last hope!

Thanks,

TJ

1 Stars2 Stars3 Stars4 Stars5 Stars6 Stars7 Stars8 Stars9 Stars10 Stars (185 votes, average: 6.58 out of 10)
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