Charlie's friends and family put a crimp in his plan for a romantic Christmas Eve date. When Evelyn sees who the date is, she goes to great lengths to force a wedge between them.

Jake shares that he has heard his mother having sex with her fiancée, Herb; this revelation brings up a repressed memory for Charlie. This leads Charlie to seek help from Rose.

Charlie takes a liking to Myra, the witty sister of Judith's fiancé, Herb.

Alan looks forward to Judith's wedding, while Charlie and Myra continue their romance.

Alan finds out some surprising information about Judith's sex life when he decides to go on a date with one of her friends.

Charlie borrowed money from Alan and on the day he is supposed to pay him back, Alan goes to ask Charlie for the money. He again finds Charlie in bed with a beautiful woman. After Charlie shoos him out and assures him he'll get the money for him later that day, the woman asks if Charlie is really out of cash and Charlie tells her not to worry, that he has plenty of hooker money.

When Judith kicks Herb to the curb, Alan comes knocking; Jake is sent to stay with a less-than-willing Charlie for three months during Judith's meltdown.

Alan tries to escape Judith's grasp as Charlie and Herb go on the prowl to pick up women. They later end up going back to Herb's hotel room with two prostitutes, where Herb declares his love for Judith and races over to win her back.

Judith is pregnant with a baby girl and Alan is convinced he is the father.

After Chelsea discovers a nude picture of another woman on Charlie's cell phone, he blows off steam by going out for a night of drinking with Alan, Herb and his neighbor.

Charlie starts to question his relationship with Chelsea when he hears that Mia is back in town. Meanwhile, Judith goes into labor and Charlie, Alan and Herb rush her to the hospital, on the sixth season finale.

Alan ends up playing maid to Judith's new baby as well as his former mother-in-law. Meanwhile, Jake uses an incriminating photo to blackmail Charlie.

Jake hopes to win back Celeste by writing her love songs. Alan and Herb hope to keep Judith from finding out they've become friends.

When Jake finds out that Alan has been dating Eldridge's mom, he packs up and heads to Judith and Herb's. Meanwhile, Charlie decides it's time to cut back on boozing.

Lyndsey and Eldridge move into Charlie's house after their home burns down.

Alan goes to great lengths to be able to get Lyndsey a nice birthday present.

Alan feels paranoid when Lyndsey becomes friendly with Charlie.

While Charlie and Rose carry on their "affair," Alan's chiropractic business turns into a Ponzi scheme.

Alan and Jake meet Walden Schmidt, a broken-hearted billionaire.

Alan prepares Walden for a date with Bridget, while Jake decides to emulate Walden and drop out of school.

Upon his release from the hospital, Alan is met with a slew of challenges that test his ability to cope.

Jake is pressured to make a decision about his future.

Alan is faced with relationship trouble when he does not give Lyndsey a key to the beach house; Walden, Alan, Herb and Billy commiserate about relationships.

After a fight with Walden, Alan decides to move in with Herb.

Alan and Walden end up partying too hard as they try to cheer up Herb.

Alan has a difficult time coping when Lyndsey breaks up with him.

A birth mother considers having Walden and Alan adopt her baby.

Walden discovers how challenging it is to be intimate with women when his foster son, Louis, is in the house. Also, Herb asks Alan if he can go on a date with Lyndsey.