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Walden begins to date a poor but ambitious woman named Kate (Brooke D'Orsay) and changes his name to "Sam Wilson", pretending to be poor to find someone who wants him for him, not for his money.They later break up when he reveals who he really is, though Kate realizes that Walden's money helped her become a successful clothing designer.Alan leaves to live with his mother Evelyn (Holland Taylor) when the house is sold, but Walden invites both Alan and Jake back to live in the beach house.He needs friends and the three form a tightknit surrogate family.Jake announces he is being shipped to Japan for a year, so Alan and he go on a father-son bonding trip.Other than a cameo in the series finale, this is the last time Jake appears on the show, though verbal references are made to him.

The first five seasons find Charlie in casual sexual relationships with numerous women until the sixth season, when he becomes engaged to Chelsea (Jennifer Taylor), but the relationship does not last as Chelsea breaks off their engagement.

Afterwards, Charlie flies to Paris in the eighth-season finale with his stalker Rose.

In the ninth-season premiere, introducing a revamped show, it is revealed that Charlie died when he fell in front of a subway train in Paris.

Suggestions are made that Rose pushed him in the train's path after learning Charlie had cheated on her. Throughout the series, Alan continues to deal with his son Jake's growing up, and the aftermath of his divorce, when he has little success with women.

His marriage to Kandi (April Bowlby) at the end of the third season was short-lived.

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