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Alan tries to have a nice hotel getaway weekend with his girlfriend, Lyndsay; Charlie orders the girlfriend experience from a prostitute.
Alan is not a fan of Jake's new bad boy friend, but is definitely a fan of his hot mother; Charlie struggles to write a theme song.
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.