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.moreless
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.