Emmy® winner Jon Cryer stars alongside the multitalented Ashton Kutcher in the Emmy®-nominated Two and a Half Men as the hit comedy series returns for its 11th season. Another year of bachelorhood brought many new adventures for roommates Walden Schmidt (Kutcher) and Alan Harper (Cryer), living in the Malibu beach house now owned by Walden, an Internet billionaire. After his girlfriend turned down his marriage proposal, Walden was thrown back into the dating world in a serious way. He even got invited to a threesome with Alan and his girlfriend, Lindsey (guest star Courtney Thorne-Smith), and created a false identity to find a girl who wasn’t after his money. The guys may have thought things were going to slow down once Alan’s son, Jake, got transferred by the Army to Japan, but they’re about to be proven wrong when a niece of Alan’s, who shares more than a few characteristics with her father, shows up at the beach house.
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.
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.”
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.
Walden starts partying with Jenny and her hot friends. Meanwhile, Alan and Lyndsey’s illicit affair is jeopardized.
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.
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.
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 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’s date with a gorgeous, accident-prone underwear model (guest star KATE MINER) goes on much longer than he 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 (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 joins his beautiful former employee, Nicole (guest star ODETTE ANABLE) on a brilliant new project. Meanwhile, Alan advises Jenny to open up to her girlfriend Brooke (guest star ALY MICHALKA) or risk losing her.
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.
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.
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.
Alan gives Lyndsey the option of choosing between him and Larry. Meanwhile, Jenny fears that she and Brooke are growing apart.
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 (guest star KIMBERLY WILLIAMS-PAISLEY).
Lyndsey discovers that Alan is sleeping with Larry’s sister, Gretchen. Meanwhile, Walden struggles with telling Barry (guest star CLARK DUKE) 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 (aka Jeff Strongman) house. BROOKE D’ORSAY returns as Walden’s ex-girlfriend Kate.
Walden reconnects with Kate and is sure she’s “The One” – that is, until he meets Vivian (guest star MILA KUNIS – That ‘70s Show, Black Swan), a beautiful, free-spirited world traveler who shows up on his doorstep. Feeling an instant connection with Vivian, he soon becomes convinced that she’s “The One.” Meanwhile, Alan and Gretchen grow closer.
Alan stumbles upon an opportunity to make money. Meanwhile, Walden has to address his co-dependency issues.
Alan’s girlfriend, Gretchen, insists that he confess his true identity to Larry. Meanwhile, Walden goes on a road trip with Jenny and Barry to see his first car.
Alan confesses his true identity to Larry and has to face the consequences on the Season Eleven Finale. Guest star Kimberly Williams-Paisley returns as Alan’s fiancée Gretchen, alongside her real-life husband BRAD PAISLEY who makes a cameo appearance.