Gary (Vince Vaughn), an affable tour guide in Chicago, is at a Cubs game with his buddy Johnny (Jon Favreau) when he spots Brooke (Jennifer Aniston) a few seats down. She's with a dorky, plaid-shorted date and doesn't look like she's having a lot of fun. Gary thinks she's cute, so he buy's her a hot dog and convinces her to leave her lame date and come out with him.
The next sequence is a series of still photos of Gary and Brooke's courtship. We find out that they go to football games, barbecue with friends, join a couples bowling league, buy a condo together—and look pretty happy together doing it.
Flash forward two years. Brooke and Gary are living together. Gary’s still a popular tour guide for a company he owns with his two brothers; Brooke works at an art gallery. On this particular day, Brooke is assisting a very attractive male customer who ultimately decides not to buy anything. She tells him to wait until he sees something he just has to own. The day ends and Brooke rushes home, seeming stressed out.
We find out that Brooke is stressed because she and Gary are having both of their families over for dinner. The families haven’t spent a lot of time together, so Brooke really wants this to go well. Gary wanders in the door and hands Brooke a small bag of three lemons. She’d asked him to pick some up on his way home and he’s proud that he remembered. But it turns out that Brooke needed 12 lemons for dinner, and Gary’s forgetfulness feels like a slap in the face. Brooke tries to get Gary to take a shower and then help her in the kitchen, but Gary says he’s tired after a long day and just needs to relax. Brooke says that she’s had a long day at work too, but she still came home, cleaned the apartment, and cooked dinner. They argue for a bit and then the doorbell rings. Brooke asks Gary to answer it, but at that moment he decides he needs to take a shower, so he leaves Brooke to deal with the arriving guests.
Dinner