- Directors: Ken Kwapis
- Producers: Drew Barrymore, Nancy Juvonen
- Writers: Greg Behrendt, Liz Tuccillo, Abby Kohn, Marc Silverstein
- Genres: Comedy, Drama, Romance
- Actors: Ben Affleck, Jennifer Aniston, Drew Barrymore, Scarlett Johansson, Justin Long, Jennifer Connelly, Ginnifer Goodwin, Kevin Connolly, Bradley Cooper, Kris Kristofferson
The plot chronicles the romantic misadventures of nine individuals in their twenties and thirties. Set in Baltimore, the common thread of the story is that one person in each relationship is more enamored with the other person than vice versa. At the core of these multiple stories is Gigi (Ginnifer Goodwin), a young woman who repeatedly misinterprets the signs that men give her about their level of interest in her.
After a rejection from Conor (Kevin Connolly), Gigi begins getting dating advice from the romantic and promiscuous Alex (Justin Long), the manager of a bar and Conor’s best friend. Alex tells Gigi that Conor simply wasn’t interested in her since he hasn’t called, otherwise he would have definitely made a move. He also tells her that she should stop thinking that she is an exception to this rule, and to stop obsessing over every “sign” that she might pick up on during a date. Gigi proceeds to go on several unsuccessful dates, often calling Alex during dates for advice. Gigi starts believing that Alex is interested in her because he is so willing to take a call from her (even when he’s busy at work, or is with a girl), and because she thinks Alex intentionally botched a blind date he organized for Gigi and one of his friends. Alex then invites Gigi to a party he’s having at his apartment. Interpreting this invitation as an opportunity to “co-host” the party, Gigi helps make food for guests, and stays behind to clean up. When all the guests are gone, Gigi kisses Alex. Alex, surprised and very frustrated, tells her he wasn’t interested in her romantically, and if he was he would’ve pursued her. Gigi tells him that even though she obsesses over everything and has embarrassed herself many times, she is closer to finding love than he is. Gigi and Alex stop speaking to each other, but Alex feels continuously troubled at work. After being confronted by one of his employees he realizes he’s obsessing and over-analyzing his situation with Gigi, in the same way Gigi was at the beginning. Meanwhile, Gigi goes on a date with Bill (Alex’s friend who was meant to go on the blind date with her). After she returns home, Alex goes to see her at her apartment. He apologizes to Gigi and kisses her, telling her that she is his exception.
Gigi’s other co-worker, Beth (Jennifer Aniston), is living with her boyfriend Neil (Ben Affleck), who is also friends with Ben, and who she has been with for seven years. Although Beth wants to get married, Neil does not believe in signing a piece of paper to say you love someone. After listening to a rant about relationships from Gigi, Beth becomes upset and starts thinking about her relationship with Neil. When she arrives home after work she asks Neil if he’ll ever marry her; when he doesn’t respond, Beth breaks up with him. Neil moves out to live in his boat while Beth goes home to see her family and to be a bridesmaid at her younger sister’s wedding. During the reception, Beth’s father has a heart attack. Beth constantly looks after her father: she brings him food and keeps him company, and cleans the house. Meanwhile all the other sisters’ husbands do is watch football, make a mess, and are not concerned at all about their father in-law. Beth is constantly frustrated and worried, but Neil suddenly appears in the kitchen helping her wash dishes. Beth goes to see Neil on his boat and they get back together, telling him that he is more of a husband than her sister’s husbands will ever be. Back at their apartment, Beth scolds Neil for bringing back a pair of pants she told him to leave on the boat. Neil insists that if she’s going to throw them out then to check the pockets for any valuables. Beth complies and discovers a box with a diamond ring, and turns around to find Neil kneeling down behind her. Neil proposes to her, telling her that for him to be happy then Beth needs to be happy. Beth accepts his proposal.