Life is anything but perfect for Kate (Jennifer Aniston). For reasons she initially can't quite fathom, the attractive and talented advertising director is having trouble advancing her career. Kate's boss, Mr. Mercer (Kevin Dunn), won't even consider her for a promotion because she is unattached, without responsibilities and, he fears, could subsequently leave the firm at any time.
Then there is Kate's meddlesome mother (Olympia Dukakis), who wants nothing more than to see her daughter married. Despite her mother's pleadings, Kate, frustrated by a seemingly endless series of dates from hell, sets her sights on co-worker Sam (Kevin Bacon). Unfortunately for Kate, Sam is only interested in women who are unavailable -- i.e. already spoken for.
How can Kate fulfill both her boss's requirements and her own romantic needs? Well, her best friend and colleague, Darcy (Illeana Douglas), has a plan. Darcy decides to take matters into her own hands by inventing a fictional fiancé for Kate. She even provides pictures of Kate with an attractive young man named Nick (Jay Mohr) as proof. Yet the truth is that Kate only just met Nick the previous week at the wedding of a mutual friend, where the fateful pictures were taken.
Kate reluctantly goes along with the idea and, as a result of Darcy's scheming fabrication, she gets her promotion -- and her man: the previously unavailable Sam suddenly finds he is attracted to the now officially unavailable Kate.
When circumstances force Kate into producing her "picture perfect" fiancé, she hunts Nick down and hires him for one evening to pose as her beloved. He agrees, and together they begin a crash course in each other's lives, creating a past history for their "relationship" -- and planning a convenient break-up to take place during a business dinner with her boss. But as Nick gets to know Kate, he becomes less happy with the situation -- he has truly fallen in love and realizes that Kate is the woman for him. Kate, though, is determined to stick with the original plan. A series of comic misunderstandings and mixed signals culminate with a crestfallen Nick deciding to head back home.
With Nick preparing to leave her life as quickly as he was hurtled into it, Kate is about to learn what truly makes the perfect mate ... and that a picture is worth much more than a thousand words.
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