Best friends FDR and Tuck are CIA agents working together. They are assigned to prevent an international criminal, Heinrich, from acquiring a weapon of mass destruction. But the mission goes wrong when Heinrich's brother is killed - making the agents a target for Heinrich. As a consequence, the agents are assigned to desk duty.
FDR and Tuck have very different attitudes when it comes to women. FDR is a womanizer, whereas Tuck is looking for love. Tuck has been unable to get back together with his son's mother, Katie, who is dating someone new. So he decides it's to get back in the game and signs up for online dating. He ends up on a date with Lauren, who has been registered on the dating site by her friend after a failed engagement. They meet at a bar for a drink and it goes well. At the end of the date, Lauren goes to the DVD store where she encounters FDR, who is looking to hook-up. FDR attempts to flirt with her, not knowing she was Tuck's date. When she rejects him, he begins to pursue her by turning up to a product testing session at her work. In an effort to get rid of him, she agrees to go on a date. The date doesn't go well, until Lauren bumps into her ex-fiance with his new girlfriend. She proceeds to pretend that FDR is her new boyfriend and that they are very much in love. She is impressed that he goes along with it. As a result, Lauren ends up dating both men - unable to decide which one she likes better.
FDR and Tuck discover that they are dating the same girl - but neither one is willing to back down. They make an agreement to carry on dating her (without her knowing that they know each other) but neither must sleep with her - it is then up to her to decide who she wants to date. However, they soon begin underhand tactics to scupper the other, using all the resources of the CIA surveillance at their disposal.
As Heinrich catches up with the agents. They are in a car chase, which Lauren is caught up in having gone to lunch with Tuck. On Lauren's advice, they shoot the headlights on Heinrich's car, deploying the airbags and sending Heinrich's car spiraling out of control. Lauren must suddenly choose which side of the road to jump to for protection - Tucks or FDRs. She chooses FDR. Tuck is gracious and declares that he is happy for them both as Lauren confesses that she wants to be with FDR. Later, Tuck reconciles with Katie.
When FDR and Tuck are about out to jump out of a Chinook helicopter, FDR tells Tuck that he is going to marry Lauren. He also reveals that he had sex with Katie before she met Tuck, and no longer feels guilty about it because Tuck had sex with Lauren. Tuck, however, reveals that they didn't go all the way and angrily tackles FDR out of the plane.