开篇用倒叙的手法讲述了汤克(戴恩•库克 Dane Cook 饰)搞砸一次约会的全过程。原来他的工作是帮助被女友甩掉的男人,替他约会前女友并恶心对方。这样女友感念前男友好,容易重归于好。不过,汤克最新接到的任务竟然来自好友达斯汀(贾森•比格斯 Jason Biggs 饰)。后者追女友亚丽克西斯(凯特•哈德森 Kate Hudson 饰)始终不得法,在公司里眼睁睁看着小白脸亲近她,却无计可施。所以,才来找汤克出手。两人约法三章,随后汤克出手,从一起跑步开始,他就成为了亚丽克西斯如影相随的伴侣,两人关系迅速升温,以至于汤克都不敢相信,自己已经离不开这个女友。他觉得困扰,于是向经验丰富的老爸(亚历克•鲍德温 Alec Baldwin 饰)求教,但是后者却鼓励他鸠占鹊巢,这让他感到左右为难……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.