Kate (Jennifer Aniston) is struggling in the advertising business in New York City: she cannot move forward despite her talent. Her boss, Mr. Mercer (Kevin Dunn), passes her up for a promotion because she is "not stable enough". Her co-worker, Darcy (Illeana Douglas), invents a story claiming Kate is engaged to Nick (Jay Mohr), a freelance videographer who lives in Massachusetts, with whom Kate had her picture taken during a friend's wedding