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Charlie runs into Chelsea's friend, Gail (Tricia Helfer); Alan starts doing in home care for an older red head (Frances Fisher).
Charlie and Alan run into Chelsea at the movie theater, prompting Chelsea to visit Charlie for a one night stand.
After Chelsea moves the rest of her things out of the house, Charlie goes on a bender that ends with him marrying another woman in Vegas.
Chelsea returns from her night with Brad and Charlie's jealousy sends her packing.
Alan gets arrested and Chelsea becomes friendly with his lawyer, Brad (Steven Eckholdt).
Charlie ends up getting a colonoscopy to avoid seeing Chelsea's parents when they come to visit.
Charlie tries to talk to Jake as he misses Celeste; Alan and Herb bond over what they have in common.
Charlie helps teach Jake about infidelity while Celeste is out of town; Evelyn invites legendary tv producer Marty Pepper (Carl Reiner) to their Christmas dinner.
Charlie goes for ball room dancing with Chelsea and when he asks for a prenup discovers Chelsea has money to protect.
Charlie fails to please Chelsea in the bedroom and plans an elaborate night out to make up for it; Alan uses spray-on hair to prepare for an online date.