Submitted by Tornado Dragon
While Mike (Jon Favreau) is having a night out on the town with Trent (Vince Vaughn), Sue (Patrick Van Horn), Rob (Ron Livingston), and Charles (Alex Désert), he meets a woman at a bar named Nikki (Brooke Langton). They get to talking, and they get along well enough that Mike gets her phone number, which she writes down on a napkin. After showing her number to his friends, they ultimately advise him to wait two days to call her because if he calls sooner than that, he might scare her away. When Mike returns to his apartment at around 2:30 a.m., he decides to call her, but he only gets her answering machine. After leaving a message, he proceeds to call her five more times in a row, and each subsequent message that he leaves sounds more desperate than the one before it. On the fifth attempt, she answers the phone before he can finish leaving his message and tells him never to call her again.
Depressed, Mike spends the next two days hiding in his apartment, and Trent calls him on the second day and leaves a message on his machine asking him to join him and their friends tonight for another night on the town. We then see an unshaven Mike sitting on the floor and going through a bunch of paraphernalia from his and Michelle’s relationship that he keeps stored in a box. Rob then pays him a surprise visit, and after Rob finds out that things didn’t pan out between Mike and Nikki, Mike tells him that he is thinking about moving back to New York City. When Rob replies that that is a dumb decision, Mike tells him that he thinks that his life in Los Angeles sucks because he has had very little success as an actor and comedian and because he has an agent that specializes in magicians. Rob then informs him about how he was recently turned down for a job playing Goofy at Disney Land, and he goes on to explain that the quality of your life all depends on how you look at it; if he (Mike) thinks that his life sucks, then that means that his life is absolutely terrible. He then tells Mike that part of the reason he moved out here was that he saw how well that he was doing out here, and he figured that, if Mike could make it, so could he. Mike replies that he hasn’t made it, but Rob counters that he has because he has an agent and he got into the unions. He then points out to Mike that he always looks at the stuff that he doesn’t have instead of the stuff that he has, and their friends are right about him when they tell him that he is “money.” Fighting back tears, Mike asks Rob why Michelle won’t call him, and Rob replies that it is because he left, plus she has her own life to deal with in New York. He tells Mike that he needs to let go of the past and get on with his life because, when he does, he will find that the future is beautiful, and he assures Mike that he WILL get over his pain eventually. He and Rob then leave to get something to eat.
That night, Mike cleans himself up, and after meeting up with Trent and Sue at the latter’s house, they all go out for another night of clubbing. They go down to the Derby for Swing Night, and after spending some time drinking and chatting, Mike goes up to the bar to order another drink. While waiting for his chance to give his order to the bartender, he spots a lovely blonde woman sitting at the other end of the bar, and after their eyes meet and they exchange smiles, he goes over to her and makes his introductions. She introduces herself as Lorraine (Heather Graham), and as they converse, he finds out that she is dealing with the same problems as he is in the romance department; she, too, broke up with a significant other months ago before moving to Los Angeles and is still having some difficulty moving past it. Soon after, she asks him to dance with her, and they proceed to have a very enjoyable swing dance together. Afterward, Mike escorts Lorraine to her car, and after they tell each other that they had a good time tonight, he tells her that he wants to see her again, so she writes her phone number on the back of one of his business cards while keeping another card for herself. When he returns home later, it looks like he might make the same mistake of calling her too soon after meeting her as he did with Nikki, but in the end, he sticks Lorraine’s number on top of the answering machine and goes to bed.
After waking up in the afternoon, Mike is almost tempted to call Lorraine, but then he suddenly gets a call from Michelle. She tells him that she has been thinking about him every day and that she misses him, and when he asks her why she never called him until now, she replies that she repeatedly tried to but couldn’t bring herself to punch in his number. After she tells him that she is calling him because she had heard that he might be moving back to New York City, he suddenly gets another call on the other line, so he puts Michelle on hold and answers it. To his surprise, he finds out that the caller is Lorraine, and he tells her that he wants to talk to her but asks her to stay on the line until he finishes the other call that he is having, after which he puts Michelle back on and tells her that he has decided against moving back. He then asks her if he can call her back, and she replies that he can’t because she is about to go out of town for a week, so he tells her that they will have to talk when she gets back because he needs to take this other call. He then says goodbye to her, but when she tries to tell him that she loves him, he hangs up on her before she finishes, a clear sign that he is finally moving on from her. He resumes his call with Lorraine, and after she tells him about how her own friends advised her to wait two days before calling him, she asks him to go out with her to a club tonight.
Mike later meets with Trent and tells him all about how he is moving on from Michelle at last and is focusing on nurturing something romantic with Lorraine.