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Mike (Steve Zahn), works at his parent's motel as the night manager. One day he sees Sue (Jennifer Aniston), who's staying at the motel for the weekend. He develops a crush on her and surprises her at her door with a bottle of wine. She's initially flabbergasted by his advances, and rushes to get him out of her room. He returns the next day, trying the same trick with champagne, and this time she allows him to touch her butt momentarily. As she heads back home the next day she decides to go back and have sex with Mike.
Mike becomes obsessed with Sue and flies to her home. She's shocked to see him there, but out of courtesy allows him to stay with her until morning when he can go back home. After spending some time together they get to know each other better as friends, and soon after Mike returns home, Sue stays at the motel again. They decide to go out and have fun. Mike's mother (Margo Martindale) is very sick, and the two stop by her home to see her. She approves of Sue, and tells Mike that he needs to find happiness in his life. Soon after Sue leaves, Mike's mother passes away. Mike decides to make a change in his life and go after Sue once again.
Mike learns that Sue has gotten back together with her old boyfriend, Jango (Woody Harrelson). Mike settles in to the new town by taking a job at a restaurant. One of the restaurant workers, Al (James Hiroyuki Liao), befriends him and allows Mike to stay in his basement. Mike skydives into Sue and Jango's pool to surprise her, but Jango responds by attacking him with a BB Gun. Feeling bad about what he did, Jango invites Mike and Al over for dinner. Nevertheless, Jango knows Mike has feelings towards Sue and threatens him. Regardless of the threat, Mike, with help from Al, sings a song for Sue outside her window later that night. Sue meets up with Mike the next day, informing him that she and Jango are getting married. Sue is also pregnant, and she wants to be with someone that's in control of his life. In anger, Mike tells Sue to leave.
Mike returns to the motel, now being run solely by his father, (Fred Ward). After talking about moving on with their lives, Mike's father hands him over the deed to the motel. Mike decides to turn the motel into a homeless shelter, something Sue had mentioned always wanting to do. Mike calls her at home to tell her, but Jango answers the phone. He reveals that Sue left him and is living with her mother. Mike makes his way to Sue's home to tell her and ask her for her help. She's happy to see him and tells him that she loves him. Mike tells her he loves her and only wants to take care of her and her baby. The story ends as they embrace.
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