» Milton’s Pimp My Look Barstool Sports: Boston

Milton’s Pimp My Look

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

Prez,

Let me start by saying Tom is THAT friend, the guy that will wear sweat pants to a party, go weeks without shaving his red pube beard, and also wears the same three shirts: Hogworks Offensive lineman camp shirt, SHS Colonials shirt, and our Football spring combine shirt that we got our Junior year of high school. The kid goes to Emmanuel, so the large percentage of women there have forced him to learn what a button-down shirt is at least. But he still needs some work, when he gets weirded out he tends to chew Redman awkwardly in the corner. That is when we call him “Awkward Tom”. He is a great guy though who is also notably Canadian and a die hard Senators fan, and is also randomly a Packers fan without ever living anywhere close to Wisconsin, but hey, you gotta love his passion.

Please help out our friend, we’re hoping this will offically turn Tom from “Awkward Tom” into “Classy Tom”.

Viva la Stool,

Dylan & Mike

(325 votes, average: 8.02 out of 10)

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By elpresidente posted October 19th, 2012 at 5:13 PM

Top 2 Comments

13 comments Sort by Popularity Sort by Date

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by Evil One on October 19, 2012 at 5:17 pm
I can't in good faith trash a fellow Canadian on a US website, however difficult that may be.pretty sweet Cosco vest though
- Up: 0
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by 4guys1barstool on October 19, 2012 at 5:19 pm
That nametag is the closest this kid's ever gonna get to any BJs
- Up: 8
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by bababooey7 on October 19, 2012 at 5:38 pm
yeah that pube-beard has gotta go corky
- Up: 1
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by Evil One on October 19, 2012 at 5:45 pm
ps, you should probably get that thing on your back looked at..........EP didn't
- Up: 1
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by otwisted on October 19, 2012 at 5:47 pm
This kid hasn't seen pussy since he came out of one.
- Up: 1
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by revnathanhortonheat on October 19, 2012 at 5:49 pm
This kids looks like every other fucker that enters this contest. They all look the same.
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by Schwet T. Balls on October 19, 2012 at 5:51 pm
By the looks of his hair in the first picture it looks like he goes weeks without showering too. All the miltons clothes in the world isn't going to get stank off this slouch.
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by CertifiedBA on October 19, 2012 at 6:40 pm
This dill-weed just needs a haircut and a shave.
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by Jeters Giftbaskets on October 19, 2012 at 6:50 pm
I can and WILL in good faith trash a fellow Canadian on a US website. The fact that this guy has a rotation of 3 t-shirts that he wears all the time is enough to explain just how disgusting he is. His friends could have emailed the pictures with that statement and this guy would have won the Miltons contest for the rest of the year.
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by dana bibles midget penis on October 19, 2012 at 9:12 pm
If I put my face close enough to my monitor I can smell cheese popcorn, but not in a good way.
- Up: 1
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by darthquider on October 19, 2012 at 9:14 pm
why do I have the feeling that this cat has dried up load on his hairy stomach everyday all day. A true modern day fabio.
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by slutnuts4 on October 19, 2012 at 9:51 pm
definitely still thinks his dick is for pissing
- Up: 0
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by Eric Cartman on October 20, 2012 at 2:53 am
Jack Osbourne?
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