A woman improves her life with a photo that makes the boss think she has a fiancee. As her career takes off, she pretends to enjoy a fling with the office lothario until the man in the photo agrees to play her fiance for an evening and they fall in love.
Adorable as she is ambitious, Kate (Jennifer Aniston) is determined to turn her mid-level advertising job into an executive position - and equally determined to tries snare Sam (Kevin Bacon), the agency's ultra-suave Romeo who prefers illicit affairs with attached women. She achieves both goals by pretending to get married to Nick (Jay Mohr), a man she met at a wedding and barely knows. But her carefully constructed fictional life comes face to face with reality when her boss wants to meet Nick, sending Kate's personal and professional worlds spinning out of control.