Gigi (GINNIFER GOODWIN) is a young woman who's so focused on finding and holding onto love that she obsesses about why men don't ever call her after their first date. Her latest neurotic-tinged obsession is with Conor (KEVIN CONNOLLY), a real estate agent who's best friends with voluptuous yoga instructor Anna (SCARLETT JOHANSSON) but wants something more from their relationship.
Conor and Gigi were set up by the latter's friend and coworker, Janine (JENNIFER CONNELLY), who's currently remodeling her home with husband Ben (BRADLEY COOPER) who she essentially pressured into marriage after dating since college. That's unlike their other friend and coworker, Beth (JENNIFER ANISTON), who can't get her boyfriend, Neil (BEN AFFLECK), to get married despite them dating for seven years and currently living together.
Newspaper ad sales rep Mary (DREW BARRYMORE) would consider herself lucky to get just that far, as she's perplexed by the array of ever-expanding technology one must check and update to see where they stand in the dating world. And then there's bar manager Alex (JUSTIN LONG) who's seemingly content just playing the field without looking for any sort of long-term relationship. When Gigi comes into his place searching for his friend Conor, Alex sets out to inform her about how and why men act the way they do, matters that still perplex the other women regardless of the seriousness of their relationships.
As Gigi and Mary continue to try to find new love in the dating pool, Conor tries to get Anna to commit to something more with him. And that's despite her now being interested in Ben who's torn between her and Janine, all while Beth eventually gives Neil an ultimatum regarding their relationship.