Logline

When a man addicted to relationships bets his best friend that he can stay away from commitment for six months, he risks losing the woman of his dreams when he can't confess his true feelings for her.

Demetri just can't stay away from relationships. He moves from one woman to the next, and these women aren't any real prize. Dismayed by his actions, Demetri's roommate Jake bets him that he can't stay away from commitment for six months. The winning prize for Jake is Demetri’s prized Super Bowl football signed by the team. If Demetri wins, he gets to take over the bigger bedroom.

At first, it’s smooth sailing for Demetri. He manages to stay away from relationships with little effort. Then a wrench is thrown into his plans when a wholesome co-worker, Corinne, becomes friendly with him. Not wanting to alienate her, Demetri agrees to take her on a date but that’s all. Before he knows it, they’re in bed together.

That isn’t against the relationship parameters set up by Jake as long as there’s no regular dating or some of the things done in a relationship, like telling each other “I love you”. Corinne wants Demetri to spend the night, but he makes up a bad excuse for why he needs to leave.

At work, things become awkward. Corinne feels like she has become a one-night stand. Demetri must tread carefully to convince her that’s not the case without spilling the real reason. Tired of the games Demetri seems to be playing, Corinne quits her job and breaks up.

Jake starts to feel badly when he sees how miserable Demetri is. He has found the woman of his dreams but can’t seriously date her or he will lose the bet. While this troubles Jake, he isn’t quite ready to throw in the towel.

Demetri makes up with Corinne again. His former girlfriend, Marilyn, a c0-worker, is not happy that he wants to see someone else. In her mind, he should be pleading for the rights to see her. She threatens to harm him if she catches him with Corinne so Demetri now feels like he is trapped.

Corinne spills the beans to Mr. Worthington about what Marilyn is up to. After chastising Demetri for not handling her on his own, he kind of understands why his employee has been so timid and fires Marilyn after he finds out she has been stealing designs, mainly from Demetri. Marilyn isn’t finished yet.

She concocts a plan to punish both Demetri and Corinne at a T-shirt convention that is coming up. There, one of Demetri’s designs sells like hotcakes while another that the couple planted ends up being the final nail for Johnson. The innocent-looking shirt morphs into one with an offensive message and gesture. The man thinking about hiring Johnson decides he is far better off not to.

Throughout the adventure, Demetri has seen himself as the hero and Marilyn as the monster. Now his vision has come true.