Trama

Tank faces the ultimate test of friendship when his best friend hires him to take his ex-girlfriend out on a lousy date in order to make her realize how great her former boyfriend is.

Dustin, an amiable guy, is in love with Alexis, a coworker. When she tells him she just wants to be friends, he hires his roommate Tank, a fast-talking, amoral scoundrel who has a side business: men whose women have dumped them hire Tank to take their ex-girlfriends out on the date from Hell, to drive the women back into their old boyfriends' arms. He takes out Alexis who, against her better judgment, decides she needs some randy fun, so Tank is in a quandary: take Alexis up on her offer, or stay true to his friend. More complications ensue as the wedding of Alexis's sister approaches. Tank seeks advice from his father, Dustin pursues Alexis, and questions of self-worth need answers.—<jhailey@hotmail.com>

Sherman 'Tank' Turner (Dane Cook) is a help line operator and a ladies' man with a hobby: If a guy loses a girl and wants her back, he gets in touch with Tank and pays him to take the girl on a bad date. Throughout the evening Tank inevitably behaves in the most moronic fashion (bad driving, bad parking, bad back stories (sleeping with an ex's pregnant sister), bad restaurant, bad service) causing the girl to realize that her ex was not really such a bad guy after all and get back to their ex.

He shares an apartment with his step cousin Dustin (Jason Biggs) who has fallen for his colleague Alexis (Kate Hudson). Dustin takes Alexis on a date and confesses his love, but she insists they remain friends (they have been dating for 5 weeks and they haven't even had sex yet). Alexis is training for the marathon.

After the date Dustin explains his situation to Tank who volunteers his services as a good friend (instead of having to pay for his services as usual). Dustin initially turns him down, not wanting Tank to be close to Alexis, but the next day sees Alexis flirting with another co-worker and begs Tank to take Alexis out. He accepts.

Tank bumps into Alexis (he joins her training run for the marathon) and they arrange to go out. He behaves badly all night, but Alexis is too drunk to care (he takes her to a strip club and still she won't care. He asks her for sex on the first date. Alexis checks with Ami (Lizzy Caplan) who tells her to go for it and get Dustin out of her system). When he drops her off, she expects him to come in but he resists the temptation out of loyalty to Dustin.

Alexis calls Dustin, but when they meet, she explains that her date with Tank has motivated her to see other men. So, now Dustin wants Tank to take her out again for a even worse date. Tank refuses, but Dustin sends Alexis roses and an apology poem in Tank's name. Alexis calls Tank at work and berates him for leaving early the previous night. Tank goes to see Alexis and they end up having casual sex on a regular basis while Dustin begins a series of desperate attempts to stay friends with her after all.

Dustin prepares to go on a date with a single mother but when he arrives to pick her up, she is breast-feeding her child. Dustin, in an effort to be funny, awkwardly remarks that he would like to have what the baby is having. The woman, now freaked out and furious, yells at Dustin and throws him out, canceling their date. Distraught, Dustin goes to Alexis's home to see her, but is told by her roommate that Alexis was busy upstairs with the guys she has been having sex with regularly. Dustin, even more upset and refusing to leave, starts to walk up the stairs only to discover that the man Alexis has been sleeping with is actually Tank. Tank and Dustin get into a fight and go separate ways.

Tank's feelings for Alexis have now grown and he decides to consult with his father Professor William Turner (Alec Baldwin). After meeting with his father, he has doubts that he is deserving of a serious relationship with her. William has a casual attitude towards women in general and says Tank is just going through a phase and his base instinct is to treat women like commodities. "Is he the best that is ever going to get for her?"

Tank goes on another bad date with a deeply orthodox Christian girl Hilary (Riki Lindhome). She cries when Tank treats her badly and Tank feels bad, so takes her out for a real date. Hilary tells Tank that he loves Alexis and to tell her about his feelings. Tank asks Alexis out on a date and takes her to prom. Alexis has a wonderful time and Tank asks Alexis to sort things out with Dustin.

Alexis meets Dustin while shopping for bridesmaid dresses for her sister's wedding and Dustin is again offended. Alexis also tells him that she is going with tank to the wedding. While attending the wedding of Alexis' sister Rachel (Diora Baird), he realizes that she is one of his previous bad dates. The groom, Josh (Taran Killam), asks Tank to keep quiet about his use of his services. After overhearing Alexis telling Rachel that she has fallen for him, Tank's guilt causes him to sabotage their relationship (by deploying his usual asshole routine during the entire wedding. He destroys the wedding cake, hits on Alexis's mother, vomits on the bride's dress and so on) and call Dustin to apologize to him.

Dustin arrives at the wedding reception and reveals Tank's schemes to Alexis. Tank points out his clients, including the groom, and is punched and thrown out. Alexis, distraught from the fact that Tank used her, and that Dustin paid to cheaply win her, never wants to see either of them again. Later, while talking with Dustin and his father, Tank realizes that he loves Alexis, and they encourage him to reconcile with her. He finds her and jogs with her for a few miles, in the attempt to make amends, but Alexis is unmoved.

Three months later, Tank is on a date when Alexis sees him and spontaneously decides to sabotage the date by embarrassing him. She walks up to him and throws wine in his face, then continues to try embarrass him by stating to the whole room that he left her pregnant. He soon catches on to her "joke", and they continue to throw insults at each other (some of which shadow previous insults they threw at each other at their second meeting), each trying to best the other in a "play argument" of insults and bantering, after which they reconcile with a kiss.

The film ends suggesting their relationship is back on. As the film's titles roll up, it is suggested that Dustin and Alexis' roommate Ami (Lizzy Caplan) hook up (or at very least have a sexual encounter if not actually a relationship).