As Walden prepares to surprise Zoey by bringing Michael Bolton to help him propose to her on her birthday, his plan goes south when she turns him down. Jake tries to adapt to life in the military.
As Walden becomes depressed following his breakup with Zoey, he finally manages to recover and sets out to get back at her.
When Alan and Lyndsey decide to have a threesome, they ask Walden to join them, only for him to have a breakdown because he's still not over Zoey.
When Missi, an attractive family friend, comes for a visit, Walden starts to think that she's flirting with him, but he soon discovers that he was wrong. Jake comes home for the weekend and develops a crush on Missi.
As Lyndsey decides to set Walden up with one of her friends to make him get over Zoey, her plan doesn't go as expected. As Walden decides to take some time off, he meets Rose, Charlie's ex, and they hit it off, much to Alan's shock.
As Walden and Rose's relationship develops, he gets a surprise call from Zoey who asks him to get back together. As Walden tells Rose the news, she sets out to sabotage his relationship with Zoey using various methods including ferrets.
Alan freaks out when he learns that Jake went AWOL from the army to have a date with Missi. As Walden hires an actress named Whitney to pretend to be his girlfriend, he ends up having feelings for her.
As Lyndsey breaks up with Alan after he shows that he's not ready for a long-term commitment, he has a change of heart and they get engaged. Walden hooks up with an older rich lady who thinks that he's poor and he goes along with it.
Alan finds himself in a tough spot when his popular second ex-wife, Kandi, comes for a visit and asks him to get back together. Walden brings Berta an expensive gift on her birthday.
As Walden gets tired of being liked only for his money, he pretends to be a regular guy and calls himself Sam. He meets an aspiring fashion designer named Kate and they get closer to each other, while Alan takes Walden's place and pretends to be a wealthy jerk.
As Walden is still pretending to be the poverty-stricken Sam, he works as a Christmas tree salesman upon Kate's urging. Walden and his internet business partner are offered a billion dollar business proposal. Alan feels sad after he has to spend Christmas by himself.
In order to help Kate out, Walden gives Alan money to invest in her fashion line. Walden's life goes downhill as he suffers from leading a double life, so he decides to devise a plan to tell Kate the truth.
Walden decides to follow Kate to New York City with Alan and confess the truth about who he is, while Alan is looking forward to watching a Broadway musical.
After breaking up with Kate, Walden hangs out with Herb, Billy and Alan who also have been dumped, as they bond over their failed relationships. The guys convince Alan to reconcile with Lyndsey.
When Jake brings over his new girlfriend, Tammy, Alan freaks out when he learns that she's a much older single mother who is a tattoo artist. Alan and Jake clash over Jake's decision to marry Tammy in Las Vegas.
As Valentine's Day arrives, Alan is preparing the perfect surprise for Lyndsey, but his plan goes south. Walden reaches out to Kate, as he asks her to give their relationship another chance.
After going to a mixer to meet someone new, Walden runs into his ex-wife Bridget, who starts taking over his life.
After Alan and Walden have a fight over a toaster, Alan moves out and stays with Herb. When Walden starts missing Alan, he ends up fighting with Herb over him.
When Walden gives Herb advice on breakups, things get out of control when Herb starts acting wild and partying non-stop. Walden and Alan try to find a way to get Herb back to normal.
After Tammy and Jake breakup, Tammy clashes with him when she finds out that he's seeing her daughter, Ashley. Things get more complicated when Ashley's much older ex-boyfriend asks her to get back together.
As Alan becomes devastated after Lyndsey breaks up with him, he ends up injuring himself while spying on her and her new boyfriend, Nick. Walden tries to lift the spirits of the despondent Alan who ends up meeting Nick's ex-wife.
In order to cheer Alan up, Walden treats him to a makeover which gets him the attention of a married woman who takes him home, while her comatose husband is there.
Jake and Alan go on a bonding trip together, where they have a heart-to-heart talk before Jake leaves for Japan. As Walden dates a hot young woman, he ends up getting attracted to her grandmother.