Narcissistic gigolo Nikki (Ashton Kutcher) lives in Los Angeles, drifting from one relationship to another without a steady job or even a place to live. He preys on women who can provide for him. After meeting Samantha (Anne Heche) at a club (where he seduces her with a cute and gutsy approach) he moves in with her, using his looks (and the morning after sleepy smile to let them leave for work, without letting them ask him to leave the house) and sexual prowess (Satisfy her, but leave room for the relationship to grow) to keep her happy (You need 26 points for them to trust you, 1 for dinner, 2 for flowers, 3 for an orgasm and so on). Once you have 26 points, you can go back to watching football. The 2nd night of sex has to be better than the first.30K people arrive in LA each month, with dreams in them to make it big. Nikki wants an easy life, get rich by lying around., live in the hills and drive a noisy sports car. He treats women as commodities and doesn't have any respect for them as persons or individuals. Before long, however, Nikki starts cheating on Samantha, first with his friend Emily (Rachel Blanchard), then with Christina (Sonia Rockwell), whom he met at another party (Nikki had thrown a party at Samantha's house when she was away to NYC on business). Emily disapproves of Nikki's free-wheeling lifestyle and has expressed a desire for a relationship, but Nikki has no real interest in her except for her wealth. Samantha catches Nikki with Christina, but they come to an uneasy arrangement where she will ignore his infidelity.While Samantha is out of town, Nikki meets a waitress named Heather (Margarita Levieva). He enlists his friend Harry (Sebastian Stan) to help him get Heather interested (He plays a big shot director taking the phone of an LA actor, but his phone rings and the Heather finds the ruse), but she does not fall for his charms. Although he eventually gets a date with her, she abandons him midway through the date. Soon after, Heather unexpectedly shows up in Samantha's pool and they end up having sex. The next morning Nikki is moving Heather's car and realizes it does not belong to her but to her "boyfriend", after she told him she was single. Nikki throws her out in anger. However, he cannot stop thinking about her, and his obsession frustrates Samantha (who just had vaginal rejuvenation surgery and cannot have sex for 5 days) to the point that she gets fed up and throws him out, quickly taking him back. Nikki, however, leaves on his own accord, still enchanted by Heather.Nikki searches for a place to stay but has a falling out with Harry (Nikki hits Harry's friend at a strip club after he talks dirty to some strippers dancing onstage), is rejected by Emily (who says she finds Nikki vain, who sleeps with women for stuff, and calls him a whore), and cannot get into the parties he once did. Harry throws Nikki out of his house and even Nikki's family rejects him. He runs into Heather at a swanky hotel, and she admits that she was only interested in him as she believed he was rich. It transpires that she is the same as Nikki, scamming rich men for money in the same way he does with women. She lets him move in with her and her stoner roommate Eva (Ashley Johnson) and they begin dating, though Heather continues to scam and hustle, with some reluctant assistance from Nikki.One day, an upset Heather reveals to Nikki that she just broke up with her fiance because she is in love with Nikki. She further tells him her fiance's family owns the New York Rangers and that he is who has been paying her bills and living expenses. Nikki, who has also fallen in love with her, is nonetheless angry that she kept her engagement from him and leaves in a huff. When he returns, he only finds a note that says she has left for New York City. At Eva's urging and with Harry paying for the airfare, Nikki follows her.He finds her at a plush penthouse and begs her to come back to LA with him. She refuses, telling him she cannot afford to let him chase his fantasies while she gets the funds they would need to live. He then proposes to her, but she tells him that she is already married, breaking his heart. Heather says that she cannot get a divorce because she needs a marriage with stability and financial security. Her husband returns home and Heather passes Nikki off as a grocery boy, dismissing him. Nikki returns to LA, finally seeing that life is worth the struggle, getting an honest job delivering groceries and living with Harry. He delivers groceries to Samantha's house, where they are picked up by the kept man who has replaced Nikki. The ending credits show Nikki feeding a mouse to Harry's African bullfrog.