Jerry (Cuba Gooding Jr.) and Nick (Horatio Sanz) are two best buddies whose love lives have hit rock bottom. For Jerry, he vomited all over his uptight, pretentious girlfriend Felicia on a hot air balloon trip prior to proposing to her. For Nick, he has trouble meeting women because he may do (or say) something weird that scares them away.
After running into a friend who has married a beautiful girl way above him, the pair tries to escape their troubles and do the same by booking a trip on board a cruise ship, after learning that the friend had met his wife on a singles' cruise, with a female-to-male ratio favoring men. On the way to the travel agency, they have an encounter in the parking lot with a straight-acting gay man. Nick and Jerry walk into the agency, realizing that the man works at the agency, and resume the argument from outside. The manager (Will Ferrell) apologizes for the exchange and books their cruise personally. However, Nick and Jerry are unaware that the travel agency manager has just played a horrid trick on them in retaliation for Nick offending what appears to be his lover after they leave.
Though the cruise ship they're to board has a large banner on the gangplank proudly proclaiming its service to the gay community, Nick and Jerry somehow miss it. After the ship leaves the dock, it becomes apparent that the ship is full of homosexual men. They both find a new best friend in Hector (Maurice Godin), who is a proud gay man that later teaches them that gay people aren't what they think. In an attempt to leave the ship, Nick fires a flare gun into the air, hoping to flag down a passing helicopter. The flare ends up hitting the chopper, causing it to crash into the sea. The next day, the passengers of the helicopter, a Swedish bikini model team and their blonde, misogynistic, sex-crazed coach Sonya (Lin Shaye), are rescued from their lifeboat by the cruise ship. Sonya catches Nick rubbing sun tan lotion one of her girls, Inga (Victoria Sylvesdt) and she attacks Nick, immediately letting him know that she does not like him. Sonya's hatred towards Nick changes after an accidential affair, Sonya falls desperately in love with Nick and wants to have sex with him again. She confronts him trying to convince him to let her perform oral sex on him. She demonstrates with a baseball bat.
Jerry tries to make the best of the situation by pursuing Gabriella (Roselyn Sanchez), the lovely straight dance instructor after she saves him from drowning in the pool until trouble boards ship in the shape of his spoiled ex-girlfriend Felicia who wants him back.
Though Nick is making progress with one of the bikini teammates, he also learns more about himself on the trip. He finds that he enjoys being in the company of the gay men who are becoming his friends, after learning that they're not much different from straight men. After waking up with one of them in the same bed, Nick, believing he may have had sex with him, thinks maybe he could be a latent homosexual. Nick says goodbye to Inga. Inga is last seen riding off on donkies with her team and horny coach gaining sexual pleasure from the animal. Nick's theory is dismissed when the man tells him nothing happened and he continues in his pursuits of the Swedish blonde.
Then, Jerry's former girlfriend finds his cruise ship and intends to reunite. She sees him performing in drag. He tries to convince her he's straight, but, at the same time, betrays Gabriella. Felicia and Jerry then go to get married and Nick kisses Jerry at the "forever hold your peace" moment and they run off to find Gabriella with Hector. Lloyd and Jerry then parachute down to the ship that Gabriella is on and they reunite and admit their love for each other and they kiss. Then Nick goes to Gettzemüllersteigen, Sweden, to find Inga, however she is in Italy for a three month modelling assignment. However, Inga has a little sister who also aspires to be a bikini model. The movie ends when Inga's mother informs Nick that the little sister's coach will be over for dinner, who turns out to be Sonya and she is delighted to see him.