Friends Bob and Max realize Bob's neighbor Zach along with his friend Stansfield are as paranoid as they are. Therapist Claire help the men when they all join her group therapy sessions. They also help her realize that her boyfriend doesn't deserve her.
In group Claire learns that Bob has a blind date. She encourages the men to follow his example. Later they convince Claire to tag along to the bar where they are all meeting their dates. Max, Zack and Stansfield have varied successes with the women they met. However Bob's date never arrives. He does help Claire lie to a competitive colleague that they run into. The next morning the men let themselves into Claire's apartment and together they assess how things went.
Claire's group catch her yawning at their sessions. Defending herself from accusations that they were boring her, she reveals that her neighbour has been having really loud sex and stopping her from sleeping. The group, talking to her neighbour, make things worse, and overhear her own sex being loudly described. As a result, Claire tries to set personal boundaries.
Stansfield becomes Claire's mailman which makes her uncomfortable. She gets him transferred which leads him to encounter a teen bully. Zack and Stansfield deal with the bully while Max bonds with an old lady that they think is responsible for the transfer. Claire's guilt forces her to come clean which makes Stansfield respect her more.
Claire declines to talk about herself so this leads the men to dig into her private life. They discover she has written an article about her patients. She informs them that it's not about them but another group that she works with. The men are convinced she likes the other group more and will abandon them. They hatch a plot to infiltrate the other group so they leave Claire. Things do not go as planned.
A corporation buys Zack and Bob's apartment building and places a video camera in the lobby. To settle the men down Claire helps them lodge a complaint. However the corporation also owns her building as well. Claire becomes paranoid when things start to go wrong with her apartment just as the men predicted.
Stansfield realizes that he has no interests that are not Zack's. Claire joins him when he decides to take up ballroom dancing. Bob enjoys a book about owls and his passion attracts a woman from work. Max rescues an owl and gives it to Bob who quickly learns that he is terrified of it.
The men go to a conspiracy theory convention to meet women. Claire goes to do research only to run into her new boyfriend. She discovers he believes in aliens. Bob is the only one who feels the need to tell Max that his marriage was too impulsive.
The men attempt to raise Claire's professional profile which leads to her getting a speaking engagement. They quickly learn she has a fear of public speaking. In their own way they help her to overcome her fear.
Zack gets a temp job at Bob's work and abuses his power to order office supplies. Bob goes along so that he can impress his coworker Kristen. Max continues his friendship with the elderly woman he met earlier. Stansfield tries to befriend a former TV magician who keeps trying to take advantage of him.
Claire's wild sister Lindsey comes to town and takes the men to a rave. She begins a relationship with Stansfield who decides to move out of his mom's place and get his own apartment. Bob ends up after the rave with a nipple ring. He meets a nurse who likes his bad boy image.
Zack, Stansfield and Max enjoy distracting Kristen's new boyfriend a little too much. Bob waits to run into Kristen at a restaurant but runs into Claire instead. They have a moment which makes Kristen jealous and wants Bob back. Later Claire denies that anything happened between her and Bob.