Richard Longman (Sarsgaard) is a dotcom millionaire who has amassed his fortune on the web, but is genuinely lonely and looking for companionship. A chance encounter with a woman named Florence (Parker) leads her to reveal that she's a stripper at a nearby club called Pandora's Box. After Richard visits her there, he offers to give her $10,000 in order to spend several days in Las Vegas with him. She agrees, under the condition that they avoid talking about personal feelings, don't kiss each other on the lips, and that there will be no intercourse.
Naturally, this all gets thrown out the door soon after. Complicating matters is Florence's friend, Jerri (Carla Gugino), who throws a wrench into the mix by showing up unannounced and making life difficult for both of them. Richard and Florence soon find themselves developing feelings for each other, but the matter of their prior arrangement leads to an emotionally-charged ending to their weekend.
- A Date with Rosie Palms:
- Richard begins the film in this way, as he's seeking someone to get him out of the rut of watching internet porn.
- Florence. On the third day, after she fakes an orgasm having sex with Richard (who feels frustrated and disappointed), she has a 'real' orgasm by masturbating to herself while he watches.
- Anywhere but Their Lips: Part of Florence's agreement with Richard is that he can't kiss her on the lips, though she ends up breaking this rule by the end of the film.
- Armor-Piercing Question: After Richard consummates his love for Florence, he's surprised and shocked when she doesn't react at all. He then asks her, "Didn't you feel anything?", to which she simply stares in dumbfounded silence.
- Bi the Way: Florence has shades of this, as she begins to passionately kiss Jerri before catching herself and saying that she doesn't want to continue.
- Fan Disservice: Occurs several times, though (in-universe) Richard isn't nearly as freaked out by it. During one notable instance, Florence dances for him in a white dress, and they begin to get intimate. It isn't until Richard puts his fingers in a very private place that he realizes that Florence is on her period, and she justifiably freaks out despite his insistence otherwise.
- The Grunting Orgasm: Richard gets one on the third day when having sex with Florence.
- Hooker with a Heart of Gold: Florence. Despite her act, it's made clear that there's much more to her than meets the eye, and Richard finds himself being attracted to her. However, this is eventually subverted by the end when she coldly tells him that he was just an agreement and nothing more. In the final scene, it's left ambiguous whether they get back together or the relationship is done for good.
- Money Is Not Power: Richard acts like he can get anything he wants due to his newfound fortune, and treats Florence this way (to the point of practically throwing money at her to continue spending time with him). It isn't until she tells him that she has no romantic interest in him near the end of the film that he finally snaps and realizes he's lost control of the situation. Whether he's moved past this or not in the "What Now?" Ending isn't made clear.
- Panty Shot
- Platonic Prostitution: Richard and Florence's agreement begins as this — she makes it clear that she only has 3 rules. One, no kissing on the lips. Two, no talking about feelings. Three, no actual sex. By the end of the film, they've broken all three of these rules, causing her to launch into a diatribe about how she doesn't care about him and was simply using him for an arrangement. The "What Now?" Ending is unclear whether they get back together or not.
- Questionable Consent: Richard and Florence's final sexual encounter at the end of the weekend. Although she doesn't resist his advances, it's made clear that she's not happy at all about the situation.
- Rape as Drama: Jerri explaining to Florence and Richard about her experience with her boyfriend. Also, by the end of the film, Richard violently rapes Florence after realizing the sex he had with her wasn't as satisfying as he thought.
- Unreliable Narrator:
- Despite her claims that she'd just been sexually assaulted by her boyfriend, Jerri immediately attempts to seduce Richard and Florence. The latter eventually catches onto what's happening and forces Jerri out.
- Florence herself has shades of this, as the story she tells about the dog in the locked car may have been a fake story she told just for Richard's benefit.
- "What Now?" Ending: The film ends with Richard going back to the club to see Florence, who was just seen beforehand playing drums and looking conflicted about what she's done. When she sees him at the club, they sit down at the table again and she smiles fondly. However, this scene may or may not be a Flashback, and whether Richard and Florence will actually pursue a real relationship this time is left unclear.