Walden gets a new toy, but soon finds his future at Nicole's startup may be limited. Meanwhile, Alan can't stay away from Lyndsey and Larry and begins dating Larry's sister.
Alan proposes to Lyndsey but ends up engaged to Judith. Meanwhile Jenny is afraid Brooke is breaking up with her.
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.
Walden and Alan throw a bachelor party for Marty once he proposes to Evelyn.
Walden is feeling frustrated because Nicole has no time for him due to a software project, so he offers to help her with it. Larry convinces Alan to go on a blind date, which Larry arranges.
Alan gives Jenny relationship advice and Walden enters into a new project with a former employee.
Jenny needs Walden’s help in getting a second date and Alan finds trouble with his girlfriend’s ex-wife.
Walden ends up on a date with a clumsy woman which extends his time with her. Alan finds himself involved with a woman who shares too much information with him.
Walden finds himself in danger and must turn to Rose for help as a result if the affair between Alan and Lindsey.
Walden and Alan plan a double date with two attractive women, but Lyndsey gets jealous and ruins the evening.
Alan persuades Walden into inviting Lynda Carter over to dinner.
Alan spends time with Lyndsey’s boyfriend in hopes of discovery why Lyndsey likes him so much. Walden encourages Jenny to take her acting career more seriously.
Walden starts partying with Jenny and her friends, eventually culminating in a massive orgy with them, Berta, and several people from the beach. Alan and Lyndsey's affair encounters some problems.
Walden finds Berta lying on his bed after injuring her and back suggests that it may be time for her to retire. Berta quits working and the guys begin the search for a new housekeeper.
Jenny moves into Evelyn’s home because of Walden’s feelings. Alan hooks up with Lyndsey even though she is seeing another man.
Charlie’s illegitimate daughter suddenly appears and Alan is surprised not only by her existence but by how much she is resembles Charlie.