Rent Picture Perfect (1997)

As 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 snare Sam, the agency's ultra-suave Romeo who prefers illicit affairs with attached women. She achieves both goals by pretending she's getting married to Nick, 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.