John (John C. Reilly) is a sad sack who has been hoping to reconcile with his wife ever since she dumped him a half-dozen years ago. But Jamie’s (Catherine Keener) announcement that she’s about to marry Tim (Matt Walsh) sends the socially-awkward loser into a tailspin that leaves him as lonely and depressed as ever. So, half out of pity, half hoping he might meet finally someone new, Jamie invites John to a party where he proceeds to drive away ever woman he meets because of his transparent display of emotional neediness.
Then, while urinating into a plant instead of a toilet, he is approached by Molly (Marisa Tomei), a fellow reveler who doesn’t hide her admiration for his endowment. Nevertheless, John still has such low self-esteem he can’t believe this gorgeous gal would even want to talk to a guy whose face favors Shrek, let alone leave with him at the end of the evening.