Kate (Jennifer Aniston) works for an ad agency but, oddly enough, has a publicity problem of her own. She is seen as too unsettled for the ad agency to consider her for a promotion because she might move on with her life as a single woman without a boyfriend. Kate's friend Darcy (Illeana Douglas) comes up with a plan to enlist Nick (Jay Mohr) to play Kate's boyfriend. Kate offers him $1,000 to come from Boston to New York for an important dinner with her boss in which she can publicly break her fake engagement to him and thus have a reason for being single. Kate would have liked a real relationship with co-worker Sam (Kevin Bacon) but it becomes apparent he is only interested in her as long as she is engaged and unavailable. Kate must learn what she values most and how to treat people who care about her over the task of pleasing her boss for a promotion.