Congrats to this month’s winner, Zak. What a disaster.

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


Winning Reader Email

Dear Pres,

Our friend Zak needs Milton’s help badly. Zak is well renowned throughout the Bryant University community as being one of the most disgusting and vile creatures to ever roam our beautiful campus. While he has never really been considered a functional member of society, his habits as well as his wardrobe have only gone downhill since attending college. He used toattempt to don the occasional wrinkled polo or beer stained dress shirts but has since resorted to wearing a combination of moldy half-zips and cut-off t-shirts to display the lack of definition in his arms that he believes gets all the bitches wet. And finally to make things work Zak’s family is already known on the Stool as his sister is the one and only Cate from URI who was featured the other day on Smokesmash Matchup from Hell. His other sister Molly attends UMass and is a future smokeshow candidate as well as being a romantic interest of the one and only #19 for our hometown Bruins. Has there ever been a family of such polar opposites on the Stool? Two with bright futures ahead while Zak’s future is in doubt without the help of you and Milton’s.

Sincerely,

The DAWG Pound