On the 10th season finale, Walden dates a hot 22-year-old (HILARY DUFF), but finds himself more interested in her worldly grandmother (MARILU HENNER). Alan & Jake take a road trip.
Alan gets a "breakover" (i.e. post-breakup makeover)! When Walden encourages a depressed Alan to update his look and start dating again, Alan faces a moral dilemma when he attracts a married woman.
Alan is devastated when Lyndsey breaks up with him, leaving Walden struggling to find a way to help him get back on his feet.
When Jake cheats on his girlfriend Tammy (JAMIE PRESSLY) with her 18-year-old daughter, Ashley (guest star EMILY OSMENT) Alan and Walden get caught in the crossfire. SCOTT BAKULA guest stars as Ashley's ex-boyfriend Jerry.
Boys Gone Wild! Walden and Alan try to cheer up a lonely Herb, but end up living it up a little too large.
Alan moves out after he and Walden get into a fight over a broken toaster. After Alan moves in with Herb, Walden feels bad and tries to apologize. But Herb gets in the way… because he doesn't want to lose his new roommate.
When Walden runs into his ex-wife Bridget at a high-end singles mixer, they talk about getting back together. But Alan feels that she might not be good for Walden.
Depressed about being single on Valentine's Day, Walden tries to convince Kate to give him another chance. Meanwhile, Alan's all-out Valentine's Day plans for Lyndsey take a turn for the worse.
Alan has concerns when Jake returns home with Tammy (guest star JAIME PRESSLY), his 36-year-old girlfriend that he's madly in love with. Meanwhile, Walden struggles to keep a secret from Alan.
Alan and Lyndsey's relationship is strained when he won't give her a key to the beach house. Meanwhile, Walden, Billy and Herb(recurring guest star RYAN STILES) commiserate about women and relationships. WILLIE GARSON guest stars as Dr. Steven Staven, Lyndsey's gynecologist who takes her on a date.
Walden and Alan visit Kate's fashion show in New York so Walden can reveal the truth about his identity. What revealed, however, is a Broadway-style song and dance performance.
Using Walden's money, Alan invests in Kate's fashion line. Meanwhile, leading a double life starts to take its toll on Walden.
Walden juggles having two identities – rich man and poor man – and "Sam Wilson" gets a new job during the holiday season, while Alan finds himself alone at Christmas.
When Alan helps Walden create a new identity in order to find a woman who isn't just after his money, he encounters a new love interest (guest star BROOKE D'ORSAY).
Alan’s “smokin’ hot,” famous ex-wife Kandi (guest star APRIL BOWLBY) wants him back. Meanwhile, Berta isn’t interested in celebrating her birthday… until Walden helps make it special.
Alan is hesitant to make a serious commitment to Lyndsey (recurring guest star COURTNEY THORNE-SMITH), but gets inspiration from an unlikely source. Meanwhile, Walden enjoys being a boy-toy for a rich older woman.