Walden suspects his new girlfriend is cheating on him. Meanwhile, Alan gets even more intertwined in Lyndsey & Larry's relationship when he starts dating Larry's sister, Gretchen.
Alan gives Lyndsey the option of choosing between him and Larry. Meanwhile, Jenny fears that she and Brooke are growing apart.
After Alan learns that Lyndsey broke up with Larry and didn't tell him, he makes a big decision. Meanwhile, Walden sets out to prove that he's a man's man.
After multimillionaire Marty Pepper proposes to Evelyn, Walden and Alan throw him a bachelor party with several of his old friends (comedy legends TIM CONWAY, STEVE LAWRENCE and GARRY MARSHALL guest star) who help him celebrate his last days of bachelorhood.
Alan lets Lyndsey's boyfriend Larry set him up on a date, while Walden offers to help Nicole with her software project, so that she will have the time to date him.
Walden joins his beautiful former employee, Nicole (guest star Odette Annable) on a brilliant new project. Meanwhile, Alan advises Jenny to open up to her girlfriend Brooke (guest star Aly Michalka) or risk losing her.
Walden helps Jenny get a second date with a one-night stand (guest star ALY MICHALKA) and Alan's transgender girlfriend's ex-wife (guest star DIANE FARR) 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. Paula Marshall returns as Alan's transgender girlfriend, Paula.
Walden’s date with an accident-prone model (Kate Miner) goes on much longer than expected. Meanwhile, Alan dates a woman who shares some surprising personal information with him.
When Larry hires a private investigator to follow Lyndsey, he tracks her to the beach house. But when Larry thinks that she's having an affair with Walden, Alan has to figure out how to clear Walden's name without outing himself. Recurring guest star MELANIE LYNSKEY returns as the neighborhood stalker Rose, who offers to help Walden out of his dilemma.
Walden and Alan find themselves on dates with two ideal women until Lyndsey's jealousy throws a wrench in their evening. Jeff Probst makes a guest appearance as himself.
When Alan learns Walden knows Wonder Woman's Lynda Carter (guest starring as herself), he asks him to set him up on a date with her. Against his better judgment, Walden agrees to invite her to the house for dinner. Mimi Rogers returns as Walden's mother, Robin.
Alan befriends Lyndsey's boyfriend Larry (guest star D.B. Sweeney) in an effort to find out what he has that Alan doesn't. Meanwhile, Walden helps Jenny be more proactive in pursuing her acting career.
Walden starts partying with Jenny and her hot friends. Meanwhile, Alan and Lyndsey's illicit affair is jeopardized.
Walden (series star Ashton Kutcher) and Alan think it may be time for Berta (series star Conchata Ferrell) to retire when she injures her back at work.
When Walden feels cramped in his own house, Jenny moves in with Evelyn (recurring star Holland Taylor) and her wealthy boyfriend, Marty (recurring guest star Carl Reiner). Meanwhile, Alan becomes Lyndsey's "other man."
On the eleventh season premiere, Alan and Berta (series star Conchata Ferrell) are shocked when Charlie's long-lost illegitimate daughter (Tamblyn) shows up at Walden's beach house to connect with what's left of her family. Having moved to LA to pursue acting, 25-year-old Jenny likes everything her dad liked... including women.
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