Gary (Vince Vaughn) spots Brooke (Jennifer Anniston) at a ball game and is instantly attracted to her, so in effort to charm her he buys her a hotdog and persuades her to go on a date with him. The two hit it off and soon enough are a couple and move into a luxurious condo together.

After a big argument about Gary not helping her enough Brooke breaks up with Gary in hope he will change his ways. But the break-up only pushes him even further away. Things start to worsen instead of improving when neither of the two will move out of the condo. But do they really want to break-up or have things just gone way too far?