Shy awkward young Mercer Advertising Agency executive Kate Mosley's life becomes increasingly complicated when she attempts to impress her boss by pretending to be engaged to wedding photographer Nick, whom she has just met.
Kate is working on a career at Mercer Advertising but is passed up for promotion because she's 'not stable enough', still being single and having no ties to the company. A story is made up about her being engaged to Nick, a guy whom she just met at a friend's wedding, and all seems to work out well for Kate. She even gets the attention of a colleague she had always wanted, but events soon take a dramatic turn, forcing her to 'present' her alleged fiance to her boss.—Malthus <[email protected]>
Kate (Jennifer Aniston) is struggling in the advertising business in New York City: she cannot move forward despite her talent. She comes up with innovative tag lines and campaign ideas and has the ability to think out of the box. She is ambitious (she wants a billboard in the middle of times square). Her boss, Mr. Mercer (Kevin Dunn), passes her up for a promotion because she is "not stable enough". She doesn't have a husband, or a house or a mortgage. She is still living like she was in college.
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 (Susan (Amelia Campbell)) wedding (which she attended due to pressure from her mom Rita Mosley (Olympia Dukakis) to meet more eligible bachelors. Kate was the only single woman at the wedding).
All seems to work out well for Kate and she gets her promotion. Dary tells everyone that Nick lives in Boston and comes in every Friday on the shuttle, to help Kate with house hunting. They are planning to get married next march, which is about 9 months away. Kate gets invited to the launch party for the big ad account she helped to land and is introduced to the client Jim Davenport (John Rothman). Sela (Anne Twomey) is Kate's team leader.
Rita also falls for Kate's story and believes that she is dating Nick. Kate sends herself flowers at the office and makes it look like they came from Nick.Meanwhile, Sam (Kevin Bacon), a colleague that Kate had always wanted, takes notice of her as she climbs the ladder of success. They have sex twice. Sam is turned on by the idea of having sex with Kate now that she is in a steady relationship with Nick.
After Nick saves a little girl from a fire and winds up in the news, Kate is forced to bring her alleged fiance to dinner with Mercer, Mrs. Mercer (Faith Prince), Jim and his wife Mrs. Davenport (Meg Gibson). Kate meets Nick, explains the situation, and asks him to "break up" with her. Nick, who already likes Kate, complies to please Kate.
As Kate and Nick get to know each other (she gives him a whole dossier of all the lies she had told people about their relationship. how they met, where they studied, likes, dislikes etc.), she starts to like him. Kate shares a story of how her father divorced her mother when Kate was 6, and then disappeared for 10 years. He came back in her life and then gifted her a beautiful watch, which Kate subsequently lost.
The night of the dinner arrives, and Kate and Nick are prepared for their "big fight". Nick charms the audience with his simplicity. He is a wedding Videographer and says it's an honor to be a part of other people's special moments. Nick tries to suppress the "fight" by complimenting her and expressing the desire for a future with Kate. However, Kate just wants the "fight" to happen. After unsuccessfully trying to drive Nick into a fight (No babies, she can't attend his parent's 35th marriage anniversary) at the dinner table, she pays a restaurant employee to call her number and tries to make it seem like Nick is having an affair with an ex-girlfriend. At first Nick is a bit lost but figures it out and finally plays along.Everyone leaves in disgust and Nick has to pay for everyone's dinner.
Sam breaks up with Kate, when he learns that she is no longer with Nick. Despite the breakup, Nick is incredibly supportive and takes the blame in front of Kate's mom and everyone else.At work, Mercer offers to remove Sela from the account and make Kate the creative director. The campaign is scheduled to go national, which means making an ad for Super Bowl. Mercer also says that nobody wants to see Nick again with her. Kate is thrown headlong into late night work and Nick continues to be super supportive to her. Kate decides to pay Nick for his time. Before leaving Nick gifts her the watch that was gifted to Kate by her father.
After a week, feeling guilty, Kate admits to Mercer (and several co-workers) her cover-up, stating that she was dressing for the job she wanted, repeating a line that Mercer had used on her earlier regarding her instability. When she tells him she is quitting, Mercer counters by admitting to her how he exaggerated his own past at one point in his life. While he lets Kate keep her job as an ad exec, he also suggests she take a few days off to go to Massachusetts and patch things up with Nick.
Kate walks in while Nick is recording a wedding and he rebuffs her attempts to patch things up until she humiliates herself in front of the soon-to-be-married couple, as Nick did in front of her boss earlier. Satisfied that the playing field has been leveled, he makes up with Kate and invites her to the wedding reception as his guest.
