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Charlie and Jake compete over a waitress; Alan and his receptionist, Melissa, try to fight their attraction towards each other.
When one of Charlie's old wing men (Emilio Estevez) dies while talking to Charlie, he rethinks his life and ends up almost proposing to Rose.
Evelyn offers to pay for Jake's college education and Alan sees no reason to work anymore. Meanwhile, Jake ends up finding a hidden cooking ability that might let him skip college.
Charlie fears for his life when Jake begins dating his neighbor's daughter and Alan gets a date at the Mercedes dealership.
When Charlie's girlfriend, Chelsea, asks him to spend the night, he feels out of his comfort zone. Meanwhile, Alan tries to follow through with Judith's punishment for Jake.
Alan tries to escape Judith's grip as Charlie and Herb go out on the town. To cover for Alan, Charlie messes with Jake.
When Judith kicks Herb out of the house, Alan swings by to pick up Jake's school book and ends up sleeping with her. While Judith cools off, Jake is sent to live with the guys for three months.
Charlie and Alan run into Jake's former teacher, Ms. Pasternak, who's now a stripper after her one night stand with Charlie. Charlie tries to help her out.
With Alan's car in the shop, Charlie is stuck driving Alan to work where he meets Alan's receptionist, Melissa (Kelly Stables).
Charlie tries to expand his interested and improve his sex life by picking up cooking. Alan tries to emulate Charlie by dating two women and once, and Jake does the same by drinking.