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.
Sherman 'Tank' Turner (Dane Cook) is a help line operator 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 causing the girl to realize that her ex wasn't really such a bad guy after all.He shares an apartment with his step cousin Dustin (Jason Biggs) who has fallen for his work colleague Alexis (Kate Hudson). Dustin takes Alexis on a date and confesses his love but she insists they remain friends. After the date Dustin explains his situation to Tank who volunteers his services. Dustin initially turns him down but the next day sees Alexis flirting with another co-worker and begs Tank to take Alexis out.Tank bumps into Alexis and they arrange to go out. He behaves badly all night but Alexis is too drunk to care. 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. 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. Tank's feelings for Alexis start to grow but after consulting with his father (Alec Baldwin) he has doubts that he is deserving of a serious relationship with her. 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 and call Dustin to apologize.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. Later while talking with Dustin and his father he realizes that he loves Alexis and they encourage him to reconcile with her. He finds her and jogs with her for a few miles but Alexis is unmoved.Three months later Tank is on a date when Alexis and her roommate Ami (Lizzy Caplan) see him. Alexis walks up to him and throws wine in his face. After engaging in a play argument they kiss. Encouraged by Tank's father Dustin gets together with Ami.