CIA agents and close friends FDR Foster and Tuck Hansen are sent on a vital mission to Hong Kong to stop the international criminal Karl Heinrich from obtaining a dangerous weapon of mass destruction. However, things take a turn for the worse when an unexpected incident leads to the death of Heinrich's brother, Jonas, which prompts Heinrich to vow revenge against them. Upon their return to America, their superior, [Collins](Angela Bassett), pulls them from fieldwork and places them on desk duty for their safety.
FDR, who cleverly disguises himself as a cruise ship captain, is a notorious womanizer, while Tuck, posing as a travel agent, struggles with his own past, including an ex-wife named [Katie](Abigail Spencer) and a son named [Joe](John Paul Ruttan). After seeing an advertisement for online dating, Tuck takes the plunge and matches with Lauren Scott, a product testing executive portrayed by [Reese Witherspoon]. Lauren is grappling with the engagement of her ex-boyfriend, and her friend Trish has signed her up on the same dating site. FDR, with his usual bravado, insists on being Tuck’s wingman during the date, lurking nearby.
As fate would have it, FDR unexpectedly encounters Lauren at a video store and attempts to charm her, oblivious to the fact that she is actually Tuck’s date. Though Lauren quickly dismisses FDR, intrigued by his reputation as a ladies' man, he is not deterred. In a bold move, FDR crashes one of Lauren's product testing sessions, leading her to agree to a date with him. While enjoying their time together, Lauren can't shake the guilt of dating two men simultaneously, but with Trish's encouragement, she decides to embrace the situation.
As FDR and Tuck both realize they are dating the same woman, they make a pact not to reveal their friendship, but temptation gets the better of them. They employ CIA technology to spy on Lauren, trying to learn her preferences and sabotage each other’s romantic endeavors. FDR and Lauren eventually spend the night together, while Tuck comes dangerously close to the same fate with her, only for Lauren to pull back, feeling conflicted. Unbeknownst to them, Tuck has tampered with FDR's spying equipment, leading him to believe that he and Lauren have already slept together.
The plot thickens when Lauren invites Tuck to lunch, just as FDR uncovers that Heinrich has arrived in America to settle the score. In a frantic attempt to warn Tuck, he crashes their lunch date, but Tuck dismisses FDR's concerns, leading to an explosive fistfight. It is in this heated moment that Lauren learns the truth about their friendship and, feeling betrayed, storms off with Trish. Tragically, they are captured by Heinrich and his henchmen, setting off a dangerous chain of events.
In a thrilling rescue, FDR and Tuck team up to save Lauren and Trish, showcasing their CIA skills during a dramatic car chase. When they finally reveal their true identities, they cleverly follow Lauren's advice and shoot out the headlights of Heinrich's vehicle, causing chaos and eventually leading to Heinrich’s demise when his car crashes off a bridge. In the end, Lauren chooses to be with FDR, while Tuck reconciles with Katie, leading to their remarriage.
In a humorous twist, the story doesn't end there. Shortly after, FDR and Tuck find themselves on a daring mission, preparing to parachute from a Chinook helicopter. In this moment, FDR surprises Tuck by announcing his intention to marry Lauren and revealing that he had an intimate encounter with Katie prior to their reunion, which no longer haunts him. Tuck, outraged that FDR believes he went all the way with Lauren, tackles him right out of the helicopter.
