In the sixth-season opener, Charlie runs into an ex-girlfriend (Rena Sofer) whose son bears a striking resemblance to him. Russell: Martin Mull. Chuck: Aaron Refvem. Brenda: Meeghan Holaway. Clive: Brendan Patrick Connor.
Alan loans Charlie money, but takes things a step too far when he tries to get the cash back. Herb: Ryan Stiles. Ginger: Lisa Jay.
It's a series of firsts for the guys as Charlie attempts cooking, Alan tries dating two women at the same time, and Jake takes a swig of beer. Katie: Bridget Flanery. Angela: Helena Mattsson. Stephanie: Nikita Ager.
Charlie romances Alan's receptionist, and Alan has a bad feeling about the outcome. Melissa: Kelly Stables.
Charlie tries to help Jake's former teacher, who became a stripper after dating him, but things go from bad to worse when she has a religious conversion.
Alan jumps at another chance with Judith after she sends Herb (Ryan Stiles) packing.
Alan tries to dodge Judith, who has become a little too needy, while Charlie and Herb go out in search of women.
Charlie's new flame wants him to spend the night at her place. Meanwhile, Alan attempts to impose a punishment on Jake.
Jake disappears with the daughter of Charlie's new neighbor, a former NFL player (Michael Clarke Duncan), and Charlie scrambles---and fumbles---to cover for him. Meanwhile, Charlie's Mercedes helps Alan get a hot date.
Alan considers early retirement when Evelyn offers to foot the bill for Jake's college education.
When Charlie's old friend and fellow womanizer (Emilio Estevez) dies, Charlie takes a hard look at his own lifestyle. James Earl Jones has a cameo.
Charlie and Jake compete to win the affection of a waitress; Alan senses sexual tension between him and his receptionist. Shelly: Carol Kane.
Judith is pregnant, and Alan suspects he's the father. Meanwhile, Jake is in a foul mood.
Melissa (Kelly Stables) doesn't think Alan's family appreciates him, so she asks him to move in with her and her mom.
Charlie ends up in couples counseling. Dr. Linda Freeman: Jane Lynch. Chelsea: Jennifer Taylor.
A flustered Charlie tries to get a half-naked woman out of his bed when he learns Chelsea is coming to see him.
Charlie declares his love to Chelsea (Jennifer Taylor), but he isn't prepared for the response he receives.
When Chelsea gets sick, Charlie takes care of her---but he also tries to resist the urge to flee.
Charlie blows off steam by sharing a drunken night with Alan, Herb and his neighbor (Michael Clarke Duncan) after Chelsea discovers nude photos of another woman on his cell phone.
Evelyn meets Chelsea for the first time, and Charlie tries to keep them from becoming friends.
Alan lets Chelsea arrange a blind date for him and her new friend, not knowing the friend is Rose (Melanie Lynskey).
Chelsea moves into the house, and Alan feels like he's being pushed out.
Alan and Chelsea bond, and their time together gives Charlie a needed break to do the things he loves doing on his own.
In the sixth-season finale, Mia comes back to town, and her return makes Charlie reconsider his feelings for Chelsea; and Alan, Charlie and Herb take Judith to the hospital when she goes into labor. Mia: Emmanuelle Vaugier.