Alan is shocked when Charlie's 25-year-old daughter shows up at Walden's beach house to connect with what's left of her family, and who happens to like everything her dad liked - including women.
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 starts partying with Jenny and her hot friends. Meanwhile, Alan and Lyndsey's illicit affair is jeopardized.
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 wants to set up a date with Lynda Carter once he learns Walden knows her; Walden begrudgingly agrees to invite Lynda over for dinner.
Walden and Alan find themselves on dates with two ideal women until Lyndsey's jealousy throws a wrench in their evening.
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 with an accident-prone model goes longer than expected. Meanwhile, Alan dates a woman who shares some surprising personal information with him.
Walden helps Jenny get a second date with a one-night stand and Alan's transgender girlfriend's ex-wife hits on him. Meanwhile, in the spirit of the holidays, Alan receives a Japanese delicacy from Jake for Christmas, and Walden's Malibu house is alive with questionable Christmas carol lyrics.
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.
Alan is upset when he discovers that Lyndsey broke up with Larry and kept this information from him. When Walden's masculinity is questioned he decides to prove he is a real man.
Alan decides to try to win Lyndsey back, while Jenny tries to do the same with Brooke when she feels Brooke pulling away.
Walden suspects his new girlfriend is cheating on him. Meanwhile, Alan gets even more intertwined in Lyndsey and Larry's relationship when he starts dating Larry's sister, Gretchen.
Lyndsey discovers that Alan is sleeping with Larry's sister, Gretchen. Meanwhile, Walden struggles with telling Barry to find his own place.
Walden gets an invitation to his ex-girlfriend's boutique opening. Meanwhile, Gretchen wants to spend more time at Alan's (a.k.a. Jeff Strongman) house.
Walden's past day or so with Kate has him convinced she is the one he will spend the rest of his life with, until a stranger knocks on his door. Alan asks Gretchen for a big commitment, but something happens that threatens their relationship.
Alan stumbles upon an opportunity to make money. Meanwhile, Walden has to address his co-dependency issues.
Alan's girlfriend, Gretchen, insists he confess his true identity to Larry. Meanwhile, Walden goes on a road trip with Jenny and Barry to see his first car.
Alan finally comes clean with Larry about he and Lyndsey. The fallout has ramifications for both weddings, with a twist no one saw coming.