The Baxter
Eliot is a dependable and reliable—though thoroughly average—young man with a streak of bad luck, terminally typecast as a nice guy in a life that mimics the clichés of typical romantic comedies. In high school he was stood up by his date on Prom night when her ex-boyfriend, the most popular kid in school, swept her off her feet while Eliot was getting drinks. In college, his next serious girlfriend's ex-boyfriend wooed her during a pep rally by announcing that he would abandon Lacrosse in favor of attending her audition to Juilliard. During business school, he and his then-girlfriend are intercepted by one of her ex-boyfriends with a puppy. Losing three girlfriends to their ex-boyfriends has made Eliot defensive at the proposition of being abandoned (yet again) and having his heart broken.
About a week before his wedding to his girlfriend, Caroline Swann, he discovers that she had a long-lost love in high school, Bradley, from whom she was inseparable. Eliot tries to keep himself composed, but even Caroline's reassurances do not convince him that her feelings for Bradley are buried. Though he makes a last-ditch effort to convince her to elope, she refuses, and Eliot starts bracing himself for the worst when Bradley drops by and begins trying to win Caroline's affections again. In frustration, Eliot has a chance encounter with an office temp, Cecil (Michelle Williams), who shares the same elevator with him while he blurts out his unfortunate past. As he resigns himself to losing Caroline to Bradley, Cecil offers him a ray of hope: she does not believe in "Baxters" and thinks that his predicament is avoidable.
The two meet up again later that night at a small club where Cecil likes to perform her original songs to finish their conversation, and Cecil states her theory: Eliot needs to take more risks. His problems began in High School when he didn't ask his first girlfriend to dance because she was on crutches, and this provided the opportunity for her ex-boyfriend to reignite her passion. Eliot decides to take more risks, though he is unsure on when and how to do so due to his reserved habits. When Cecil has a fight with her boyfriend later that night, Eliot offers to put her up for the night.
The next morning, Caroline and their wedding planner (Peter Dinklage), show up early to finalize their plans. Cecil wakes up Eliot, and he rushes to get ready in time for their arrival, and even though the night before had been completely innocent, he panics while getting ready and accidentally puts on Cecil's underwear instead of his own. After an accidental spill, the wedding planner spots the panties on Eliot, which completely breaks down Eliot's calm. During the meeting, Eliot makes a string of awkward suggestions, ranging from asking for a "funk" music theme and "baja cuisine" for their dinner plans. Caroline, visibly upset, begins to doubt their relationship and almost runs into the hiding Cecil a few times, though Eliot manages to cover.
After the meeting with the wedding planner, Caroline calls off the wedding. Eliot, having been stood up for a dinner with his parents, goes out to a bar with his friends from work where he accidentally runs into Cecil's boyfriend, Dan (Paul Rudd), and Bradley with his current girlfriend. Though awkward at first, Dan dismisses any conflict when he realizes that Eliot is "the Baxter" that Cecil mentioned and actually thanks him for letting her stay at his house when they fought. Dan and Bradley (now revealed that Bradley's girlfriend is an old friend of Dan) insist that the groups spend some time together and chat, much to Eliot's chagrin. Both Dan and Bradley laugh and joke with Eliot's friends, until one of them mentions that Caroline left him. Depressed and upset, Eliot leaves and contemplates suicide until he is interrupted by his friend, Louis (David Wain), who gives him a pep talk on behalf of Caroline, who was worried about him.
On Louis' advice, he buys flowers, candies, and plans to take Caroline wherever it will take to make things right. When he arrives, he finds Bradley already at Caroline's apartment, swooning over Caroline and upset about breaking up with his girlfriend. They cancel his reservations to an expensive restaurant and go instead to a burger place that Bradley knows well. Eliot feels awkward because of Bradley's personal connections to the owner and patrons, while Eliot's refined tastes clash with the blue-collar atmosphere. Even with the owner's help, Eliot continues to feel out-of-place and eventually calls Cecil from the back of the restaurant, confessing that he feels that his marriage will be over before it begins.
The next day, Eliot arrives at work to find that Cecil is his temp again due to a flu going around the office. When she proposes that they both go out and have a drink to celebrate their mutual misery, Eliot explains that after his phone call, the night actually got better for him. After their somewhat disastrous dinner, Bradley and Caroline demanded to go dancing and accused Eliot of being neither spontaneous nor romantic; he stands up for himself and defends his actions and firmly states that he is trying his best to change for her. At the end of his speech, he also reveals that he has changed his mind and now wants to go dancing with them, having convinced himself to try even harder to change for her—and reminding himself that his problems began when he didn't ask his first girlfriend to dance when he had the chance. Though embarrassed, the throws caution to the wind and accepts a lighthearted dance-off against Bradley, a former break-dancer. By accident, Bradley's final move, a spinning windmill, bumps Eliot in the face, both knocking him to the floor and bloodying his nose. Bradley apologizes and reveals, to everyone's surprise, that he will leave the next day with his science team.
Though happy for him, Cecil is saddened by the news because, like Eliot, she has always seen herself as a "Baxter" and hoped that the two could commiserate together. When Eliot asks what she'll do next, she mentions that Dan has a new job in Cincinnati, and she'll probably follow him there to resume her singing there.
At Caroline and Eliot's wedding, Bradley crashes the ceremony and declares his love for Caroline—a split second after Eliot has started his own objection—and Bradley and Caroline live happily ever after, according to Eliot. He takes off immediately to catch Cecil before she leaves town, and after a near-miss, finds her at her apartment. The two talk for a moment and Eliot declares his love, when the sudden appearance of one of Cecil's old boyfriends interrupts them. Eliot, refusing to let history repeat itself, simply chases him off rather than let him get started with another speech. The film closes with the pair performing in the same club where they had their first date, with Cecil singing one of her songs and Eliot playing the piano to back her up.
In a mid-credits scene, the film returns to Eliot catching Cecil about to leave with Dan for Cincinnati. Narration begins, mirroring the narration done by Eliot in the beginning of the film, with Dan revealing himself to be a Baxter as well, describing his lament at losing the girl (Cecil) to the leading man (Eliot).
whimsical, romantic, psychedelic, satire, flashback