A new family member arrives to surprise everyone as Charlie's daughter arrives to meet her family. It turns out she has more in common with her father than expected.
Walden finally gets fed up and kicks Jenny out, so she moves in with her grandmother Evelyn and her 91 year old boyfriend, Marty. Alan is surprised when Lyndsey wants him back in her life, partially.
When Berta hurts her back, Walden and Alan start looking for another housekeeper.
Walden joins Jenny and her girl friends on the town while Alan dates another woman to protect his affair with Lyndsey.
Alan's curiosity about Lyndsey's boyfriend overwhelms him, and he secretly becomes his friend. Walden makes a concerted effort to help Jenny pursue her acting career.
Alan's obsession with Lynda Carter explodes when he meets her while attending a charity event with Walden.
Alan and Walden's date with two hot young ladies is interrupted by a very jealous Lyndsey, leading to an ultimatum.
Lyndsey's boyfriend finds out she is having an affair but Walden ends up paying the price when Rose enters the picture.
Walden's date turns out to be a fixer upper while Alan dates a beautiful woman with an unusual background.
Jenny is distressed when a girl she likes treats her like a one night stand, so Walden decides to intervene. Meanwhile, Alan gets hit on by his new girlfriend's ex-wife.
Walden starts working with a former employee on one of her ideas but has trouble not being the boss. Jenny is having a difficult time with being vulnerable to Brooke.
Alan accepts an offer by Lyndsey's boyfriend to set him up on a blind date, much to Lyndsey's annoyance. Walden pursues Nicole, and offers to help her finish her project to free up time for him.
Marty Pepper asks Alan's mother Evelyn to marry him, and Alan and Walden throw Marty a bachelor party.
When Alan learns that Lyndsey is no longer with Larry, he tries to move back in but she wants a commitment. Walden tries to prove to Jenny and Brooke that he can be a manly man.
Alan decides to try to win Lyndsey back, while Jenny tries to do the same with Brooke when she feels Brooke pulling away.
Alan can't seem to help himself as he becomes more and more involved with Lyndsey and Larry, to the point of dating Larry's sister. Walden is concerned when Nicole starts canceling dates with him.
Co-Guest Stars: Kimberly Moss
as Computer Voice (as Kimberly D. Brooks)
Lyndsey discovers that Alan is sleeping with Larry's sister, Gretchen. Meanwhile, Walden struggles with telling Barry to find his own place.