Picture Perfect (1997)

Synopsis
Friends star Jennifer Aniston made her debut as the leading lady of a feature film in this romantic comedy. Kate (Aniston) is an art director with an advertising agency whose personal and professional life is stuck in neutral; while her work is good, her boss Mr. Mercer (Kevin Dunn) won't give her a promotion, and while Kate is attracted to co-worker Sam (Kevin Bacon), he's not interested in her. Kate learns that Mercer is loath to promote single people, because without permanent attachments they're free to leave whenever they wish. Kate's friend Darcy (Illeana Douglas) comes up with a possible solution: use a photo of Kate with handsome stranger Nick (Jay Mohr) to convince Mercer that she's engaged to be married. The ruse works -- Kate gets her promotion, and Sam, who's attracted to women who are already spoken for, starts showing her some attention. But soon Mercer wants to meet Kate's husband-to-be; Kate tracks down Nick and persuades him to pose as her intended for an evening, but Nick decides at the end of the night that he's in love with her. Picture Perfect was written and directed by Glenn Gordon Caron, who created the TV series Moonlighting. ~ Mark Deming, All Movie Guide