Dustin (Jason Biggs) is a good guy who has gotten "hottie" Alexis (Kate Hudson) to go out a few times with him. She's all that Dustin has ever hoped for and he wants to take their so called relationship to the next level. But as he constantly pushes Alexis to get closer, he in turn pushes her away. She realizes she really has not been out there dating much and puts the brakes on Dustin in order to pursue going out with other men.
Sherman "Tank" Turner (Dane Cook), is best friends with Dustin and has no problem getting the chicks. His style is smooth, his lines work their magic but basically he is an uncaring, arrogant, insenstive jerk, trying to score with the ladies, following in his dad's, Professor Turner (Alec Baldwin), footsteps.
Dustin gets a hair brain idea that if he sicks Sherman on Alexis, she will see what a jerk the other men out there are, and come running back to him with open arms. Alexis takes the bait and as Sherman feeds the lines he knows should work, Alexis takes him in a different direction until he starts having feelings for her. But where does that leave Dustin? Now Sherman must decide which is the right thing to do - dump the true love he has finally found, or dump the friendship he's had with Dustin for years.
Director: Howard Deutch
Writer: Jordan B. Cahan
Producers: Adam Herz, Josh Shader, Barry Katz