Submitted by Tornado Dragon
Some days after Henry (Joseph Cross) uses his medical knowledge to save the life of her boyfriend Buck (Samuel Page) when he overdoses on cocaine at her birthday party, Scarlett (Sarah Roemer) has a chat with Henry and tells him that she wants to thank him by taking him somewhere. He replies that that isn’t a good idea because the superintendent George (Joe Pantoliano) will fire him for fraternizing with a resident and he can’t afford that right now, so she tells him to just think of their get-together as a “meeting”. She then tells him that it takes place tomorrow before giving him the time and address of the place he is to meet her at, and she promises to keep silent about it. Their “meeting” sees them taking a ferry ride around the Hudson River that goes on into the night, and they spend the whole ride getting to know each other better until they end up sharing a kiss, and they kiss again outside her apartment building before they part ways. Off-screen, Scarlett decides to break up with Buck, having had enough of dealing with his intoxicant abuse.
The next morning, Scarlett’s mother Meredith (Mimi Rogers) is busy chatting with someone on the phone when she comes across Scarlett’s purse and notices that her digital camera is sticking out of it. She decides to check out the photos on it, and she discovers that a couple of the photos are ones that Henry took of himself with Scarlett while they were on the ferry. Feeling that her daughter should not be associating herself with people below their station and worrying about how her own image will be affected if everybody saw Scarlett dating “the help”, she contacts George and fills him in on what Henry did. He calls Henry in and confronts him with this information, and though Henry tries to explain himself, George fires him. Afterwards, Henry attempts to call Scarlett on the lobby’s phone without George knowing in order to tell her that he has been let go, but George catches him before he can talk to her, leaving him no choice but to flee the building. He meets up with his sister Cate (Rachael Leigh Cook) in Central Park after telling her over the phone that he got fired, and when she asks why this happened to him, he tells her that it is because he went on a date with Scarlett and the superintendent found out about it. He expresses his worry over how he is going to obtain another job, but Cate replies that he shouldn’t be worrying about that because jobs grow on trees; the real question is what he intends to do about Scarlett. Henry replies that he isn’t going to do anything about her because her family got him fired, and he feels that he will always be seen as a doorman to her class of people.
Scarlett later comes down to the front desk with a note for Henry, but Raul (Snoop Dogg) tells her that she ought to speak with George about him. She does so and learns about Henry’s termination, and after she returns to her apartment, she finds out through a note she randomly takes notice of that Meredith had something to do with it. She confronts her mother and demands to know what she did to Henry, so Meredith tells her that she had him fired and then gives her the aforementioned reasons why she did it. Scarlett reacts to this by calling her an elitist snob and telling her that she will date whomever she wants to date, and she will date them not because of what kind of job they hold, but because of who they are as a person. She then goes down to George’s office and demands that he hire Henry back, but he refuses, and when she then asks him to give her Henry’s phone number, he won’t provide that, either. She thus resolves to call every number registered to a Henry O’Shea until she finds him.
Cate then suddenly shows up in the lobby, and she first meets Raul before telling him to fetch Scarlett for her because she wants to have a chat with her. He does as she asks, and Scarlett comes down and takes a walk with her. She tells Cate that she blames herself for what happened to Henry because she insisted that they go out despite his reluctance, but Cate replies that it was his own fault that he got fired. Scarlett then tells her that maybe she can help him get his job back, but Cate replies that maybe she shouldn’t because she feels that Henry needs to go back to nursing school. Scarlett then gets to thinking that maybe she should help him out that way.
Meanwhile, Henry discovers that his mother, Grace (Annette O’Toole), has taken up a job working in a porn shop and is shocked and sickened by it, but Grace tells him that she enjoys working there. As they are arguing about it, Scarlett comes in, and after she and Grace make their introductions, Scarlett tells Henry that she talked to Cate and she said that he might be here. She first apologizes for him getting fired before telling him that she really wants to fix it. They take their conversation outside, and she explains that she wants to help him find another job and will even get help from her father Phillip (Jim Piddock) to make it happen, but he refuses this, saying that he can take care of himself and his family. When he then asks her what they are doing here, she replies that she really likes him and really wants to see him again, but he basically tells her that he feels overwhelmed by her wealthy, high-class status and doesn’t know what a guy like him could ever possibly hope to offer someone like her. Dejected, she tells Henry to have a nice life and then leaves. As Henry starts to regret what he just said, Cate shows up, and when she asks Henry if Scarlett found him, he replies that she just left. Grace then comes out and asks Henry about Scarlett, and after he tells her and Cate that he doesn’t want to talk about it, Cate fills Grace in on who Scarlett is and how Henry got fired for going on a date with her. Henry explains that he feels that dating a rich girl like her is a pipe dream and that her parents would never allow her to date a guy like him, and then he proceeds to devalue his own self-worth and the worth of his family because of the jobs they hold (or aspire to hold, in Henry’s case), saying that this shows that they and Scarlett’s world don’t mix. Grace criticizes her son for insulting himself and his family and labelling the entire world, telling him that the quality of one’s character is what defines who they are, and no girl is too good for him and Scarlett would be lucky to be loved by a man like him. Henry then walks off, taking a long trek through the city that goes into the night.
Henry eventually realizes how stupid he was to let Scarlett go, so he runs over to her apartment building to talk to her. He finds Raul manning the front desk and begs him to call Scarlett, but he informs him that she is down at the Gotham Club with her family right now. After getting the address from Raul, Henry immediately heads over there, but he is denied access by the doorman because his attire doesn’t meet the club’s dress code. Henry therefore sneaks in through a back entrance and goes into the kitchen, where he dons a chef’s uniform and then makes his way out to the table that Scarlett and her parents are sitting at. Though Phillip is impressed and amused with Henry for dressing up like this just to get into the club and remembers how he was the one who saved Buck’s life, Meredith doesn’t care for his presence at all and asks for a staff member to kick him out. Henry tells Scarlett that what he said to her before was a bunch of nonsense and that he doesn’t really care about their different social and economic statuses, and he hasn’t stopped thinking about her since the first time he saw her on the day he got hired. The staff member then grabs hold of Henry, but Scarlett orders him to let Henry go and then tells her mother that she is leaving with him. When Meredith protests, Scarlett announces to everyone that Meredith Dowling’s daughter is leaving with the doorman – or ex-doorman, since Meredith had him fired. As they go, Meredith orders Scarlett to come back to the table, but Phillip tells her to be quiet and to leave Scarlett and Henry alone. During their departure, they run into Buck walking in with his arm around Scarlett’s friend Gretchen (Frankie Shaw). Buck shows that he is struggling with sobriety, and Scarlett then calls Gretchen a hooker since she evidently wanted Buck for a long time and moved in on him like a hawk the second he became available. Henry and Scarlett then go outside and kiss.
The movie closes with Henry and Scarlett out on a double date with Cate and Raul (Raul had shown an attraction to Cate back when they first met).