Anger Management

Kate starts feeling even more like she and Charlie are becoming a couple, when he takes her to his sister’s baby shower and the two start beating married couples at a version of the "Newlywed Game." Charlie then loses control of his anger when his sister becomes overly judgmental of both him and Kate. Meanwhile Patrick is convinced that Ed’s daughter is a lesbian, and tries to tell him.

Charlie grows concerned when his father begins to express signs of Alzheimer’s disease. Patrick tries to help Nolan dress for success.

Charlie worries about ethical boundaries when he begins dating a sexy former patient (Kate Reinders). But he soon learns that her other previous therapists, including his arch-enemy Dr. Lesley Moore (Steve Valentine), are after the same thing that he is.

Charlie thinks that his father has gotten mixed up with a bad crowd of rogue senior citizens, until he learns that Martin is the ringleader.

After a black mold outbreak, Jennifer and Sam temporarily move in with Charlie while their house gets fumigated. Kate is less than pleased to learn that Jen and Charlie will be living together.

Ed has been crankier than usual, so Charlie and the group persuade him to take a placebo pill that supposedly reduces anger. The plan seems to work out great and Ed claims that he no longer needs therapy, but it eventually backfires sending Ed back to Charlie’s group. Jennifer wants to know Kate better, so she insists that Charlie let her go out with them.

Charlie dates his daughter’s teacher after meeting with her to discuss Sam’s grades, and he soon starts to fear that Sam’s grades are related to how well he performs in bed.

Charlie takes on Cee Lo Green as an anger therapy patient. Cee Lo’s requests go way beyond anger management, but Charlie is reluctant to back out because it may jeopardize the dream job that Cee Lo helped Patrick land.

Nolan has become unusually quiet in group therapy, so Charlie gives him a weekend assignment to paint his feelings. Lacey takes a surprising liking to the macabre work of art.

Charlie gets into an argument with Martin after he finds out he had Sam baptized behind his back.

Lori (Denise Richards), the gorgeous yet eccentric woman who dated Charlie previously, returns and wants to start things anew. But Charlie realizes she can only enjoy sex with him when she’s angry. While out on the town with Jennifer, Kate gets ignored as all the men hit on Jen. Kate discovers she is giving off a "vibe" that she’s attached. Meanwhile, Patrick and Ed compete to find the ideal rich guy for Lacey.

To help keep her anger under control on the set of a commercial, Lindsay Lohan (playing herself) hires Charlie to be her anger management consultant. The two get romantic, leading to a series of mishaps that damage Lindsay’s already tarnished reputation.

When a neighbor gets wind that patients with anger issues are meeting at Charlie’s house, he organizes a protest to get the group relocated. Lacey encounters the neighbor and only makes the situation worse, Meanwhile Kate helps Jen pick a dress for Sam’s prom.

When Sam’s favorite horse from her riding stable is relocated to an "equine therapy" farm, Charlie decides a visit to the farm might be beneficial to his anger group. While the group bickers over dividing up the chores to care for the horse, Charlie and Kate sneak the horse out for a romantic evening ride, with disastrous results.

When Lacey has her driver license suspended again due to a fit of anger over her latest date, Charlie confronts her about the type of man she always seems to hook up with and inadvertently pushes her into a date with Nolan. Lacey returns to the next session and announces that she and Nolan are a couple, but it is clear she is just using him to drive her around and do her bidding. While on a "date" with Nolan at a 7–11, Lacey is caught shoplifting, thus violating her probation and sending her to jail.

Trying to help Nolan stand on his own, Charlie convinces Kate to give him a job as her receptionist. When Nolan leaks to Charlie that he found dirty pictures of Kate in an outgoing mail envelope, Charlie resolves to find out who is receiving the photos and why. Meanwhile, Charlie facilitates an anger therapy session in a women’s prison, and Lacey is one of the group members.

Charlie is asked to fill in as coach of a high school baseball team, and Martin convinces him to take him along as his assistant coach. It becomes clear that little has changed since Martin used to be Charlie’s manager. In Charlie’s absence, Kate fills in as his anger group’s therapist, but her methods sharply contrast with Charlie’s.

When Jen gives Patrick some good advice following a break-up and the two start hanging together, she announces to Charlie that she’s found her calling and is starting a career as a "life coach". Meanwhile, Lacey tries to introduce Martin to 21st century dating, and helps him set up a Facebook page.

As Martin tries to get Charlie and Jen back together, he inadvertently pushes Kate to make a decision that could solidify her and Charlie as a couple. Meanwhile, Ed is ecstatic to have the house to himself as his wife goes out of town for six days, but he has to call in his "anger buddy" Nolan when a situation arises on the homefront.

Sean (Brian Austin Green), Jennifer’s ne’er-do-well boyfriend from Season 1, is back in her life. Much to Charlie’s irritation, Sam starts to bond with Sean, even taking her first driving lesson with him. Charlie determines that his therapy group is too hung up on their petty problems, so for their next session he has them report to a soup kitchen to help the homeless. Meanwhile, Charlie finds he can’t go along with his and Kate’s new "just friends" status, so he doesn’t want her as a therapist, either.

Charlie becomes concerned when his new therapist (Marion Ross) only seems to dole out motherly advice. Meanwhile, anger leads Patrick to pull a lottery prank on Ed, which has unintended consequences.

Charlie reluctantly agrees to help Kate with a study that compares the relative sexual satisfaction of couples in committed, monogamous relationships with those in casual relationships, but their issues with each other cloud their judgment in selecting candidates. Meanwhile, Lacey has started a new job as a pharmaceutical rep that requires six weeks of training, and wants to get fired from her current job so she can collect unemployment. So she enlists both Nolan’s and Patrick’s help in getting her fired.

Sean gets arrested after decking a man who grabbed Jen’s rear end, and is required to join Charlie’s therapy group. After a rift in Sean’s first session, he reveals to Charlie that he used to be an escort. Charlie tries to figure out a way to let Jen know without breaking confidentiality. Meanwhile, Ed continues to stay in Patrick’s home, but has issues when Patrick gets rid of his TV.

Charlie is attracted to the sexy woman Tracey (Mircea Monroe) who is in his and Kate’s study with her boyfriend Matt. As they split up and she says she’s looking for a friend with benefits, Charlie is eager to help her. But he soon realizes she’s way too clingy and (without knowing) looking for a relationship. Charlie tells her, they split up, and she gets back together with her ex. Meanwhile, Patrick introduces a 73-year old friend of his, Carol (Carol Kane), to Nolan. Nolan and her get along great and even have sex after smoking pot. But in the end, Nolan realizes what she means to Patrick and breaks up with her.

Charlie arranges a trip to Lake Tahoe for his therapy group to celebrate their 30th consecutive day without an anger incident among them. While the group is stuck at San Francisco airport, Charlie receives a text from Kate which makes him think she has reconsidered and wants a relationship with him, but it turns out to be a mistake caused by her phone’s auto-correct feature. Meanwhile, Michael is put in charge of Charlie’s house while he is gone, and he learns that Jen has rented it out to a film crew.

Charlie dates a hot techie named Monica (Nicole Travolta) who wires all the electrical devices in his house so that they can be controlled via the internet. But the house goes crazy when Monica’s ex-boyfriend, another IT nerd, becomes jealous and vows to make Charlie’s life a living hell. Meanwhile, Lacey’s first sales call in her new job as a pharmaceutical rep doesn’t go as planned.

After his prison group therapy session, Charlie meets a hot woman named Wynona (LeAnn Rimes), who is on the way in to visit her brother. After they have been sleeping together for two weeks, he finds out she is Wayne’s sister and worries that she may have inherited the same tendencies as her brother. Meanwhile, Patrick learns that Nolan refused a date with an interested waitress because Lacey puts on a show for him every night from her bedroom window.

After seeing how Lacey and Sean are acting in a group session, Charlie becomes convinced that Sean is cheating on Jen with Lacey. When Sean confides that he has secretly been meeting Lacey for her help in getting a job at one of the local night clubs, Charlie realizes he was wrong about them...or is he? Jen breaks up with Sean and almost immediately hooks up with a nature-loving beach bum named Canvas (Greg Cipes). Meanwhile, Nolan is freaked out after his apartment is robbed, and Patrick and Ed stay over with him. Patrick is shocked to see the kind of poverty that Nolan is living in.

While driving with Ed, Martin hits a woman and takes off. Ed convinces him to empty his bank account and hide the money in case the woman’s family sues, so Martin gives $35,000 each to Charlie, Jen and Sam. When it turns out the woman’s family isn’t going to sue, as she is a former stuntwoman with dementia, Martin wants the money back. But Sam’s has been put into a college fund, and Jen spent hers on a food truck that specializes in year-round thanksgiving meals. Meanwhile, Lacey is bribed by Patrick into taking Nolan out on the town, then actually gets jealous when Nolan spends most of the night with her sister, Satine.

Kate tells Charlie that a 32-year old virgin patient of hers is looking for a "first experience" that won’t be traumatizing, and Kate thinks a "close friend" might be the ideal sex surrogate. Charlie assumes it’s him, approaches the woman, and they sleep together. But in the meantime Kate decided to go with a professional sex surrogate, and later tells Charlie that he was not the "friend" she had in mind. Meanwhile, Sam and Canvas get temporary tattoos to test Jen, but Jen thinks they are real and is sure that Charlie will freak out. So Jen gets a real tattoo in the same place as Sam’s, so she can tell Charlie it was a mother-daughter thing.

Charlie misinterprets Jen’s suggestion that Canvas feng shui his house and winds up throwing a barbecue. Canvas makes some unintended snarky comments about Charlie’s age, so Charlie challenges him to a one-on-one basketball match. After losing several games, Charlie finally wins by forfeit when Canvas twists his ankle. Later that night, Canvas passes away after having sex with Jen. Both Jen and Charlie think they killed him, but it turns out Canvas had a heart condition that he ignored. Meanwhile, Lacey announces that she has landed her first photo shoot as a model, but the clothing she has to model isn’t what she expected.

Michael accompanies Charlie to his prison group as part of a program to teach inmates the real estate business. Both get trapped when a prison riot breaks out. Kate worries about Charlie upon learning of the riot on the news, and her reaction after he returns to work safely has Charlie believing for sure that she has feelings for him.

After Charlie and Kate pitch an organization for additional funding on their project, Kate notices the coordinator, Lisa (Michaela Watkins), appears lonely and suggests Charlie sleep with her to "seal the deal." It turns out Lisa is gay and is attracted to Kate, which has Charlie laughing until Kate finds out that the woman’s male boss – Dr. Lesley Moore – really controls the purse strings. Meanwhile, Nolan meets a woman online that turns out to be a 10-year old girl who begins blackmailing him.

Charlie asks Jen to play a scientist looking for a research grant, so he can get Dr. Moore (the man Kate wants to sleep with) to admit that he sleeps with candidates then doesn’t give them any grant money. Although the sting eventually succeeds, Charlie finds a note from Kate stating she has left town, disgusted with herself that she was willing to have sex for a grant. Meanwhile, Lacey brings Martin along to her yoga class and asks him to pretend to be her father, so that her hot instructor will see her as a kindhearted woman.

To get over Kate moving away, Charlie has taken to drinking heavily. Sean agrees to help Charlie plan the ultimate party, but only if Charlie will convince Jen to give Sean another chance. Meanwhile, Ed is trying to win back his estranged wife, and he asks Lacey to hook him up with a prescription ointment for his manhood.

Charlie invites Ellie (Brea Grant), an attractive grad-student, to observe a therapy session only to have to compete with Nolan for her affection. Meanwhile, Ed and Martin come up with a plan to scam the government by hosting a disabled war veteran in their house.

Charlie interviews possible replacements for Kate to help with his sex study, but then learns that psychologist Dr. Jordan Denby (Laura Bell Bundy) has already been appointed by the grant foundation to take the spot. Meanwhile, Jen and Lacey plot their revenge against Sean.

Charlie is introduced to Blake (Gina La Piana), a recovering alcoholic and Jordan’s AA sponsor. Blake is later revealed to also be a recovering sex addict, and Charlie can’t help fueling her addiction. Meanwhile, Ed helps Patrick with a challenging full-figure dress design.

Charlie accepts a new patient, a pimp named Ray James II, into his therapy group. After Charlie sleeps with a young woman called Sasha (Anna Hutchison) who approached him at the bar, she reveals that she’s a hooker and that Ray sent her as payment for his sessions. Meanwhile, Lacey, Nolan and Ed are creeped out by Ray, and attempt to hold their own self-help session without Charlie present.

Charlie invites a new therapy patient named Bob (Bob Clendenin) into the group, who casually tells everyone that he is the devil. Nolan makes a deal with Bob to sell his soul in exchange for Lacey falling in love with him. When Lacey is all over Nolan at the next session, even the skeptical Charlie starts to wonder. Meanwhile, Jen falls for a new neighbor while Sam falls for a young man who appears to be the neighbor’s son, but the two are later revealed to be gay.

Charlie finally gives in and tries to help Sean reconnect with Jen, but after Jen reiterates how much she "hates, hates, hates" Sean, she sleeps with Charlie. Sean is angered, but appears to rebound when Jordan reveals the two are dating. When Jen wants to know more about the woman Sean is dating, Charlie realizes Sean is just using Jordan to make Jen jealous. Meanwhile, Patrick is convinced his good looks make it impossible for him to meet anyone other than shallow men, so he has Lacey and Nolan "ugly" him up for a night out.

Lacey’s parents cut her off, so Charlie agrees to help her out by talking to her parents at dinner. After Charlie says how mature and responsible Lacey has gotten, her parents decide it’s time for her to move to India for an arranged marriage. In an effort to prevent this from happening, Charlie says that Lacey is already in a serious relationship. Patrick agrees to pretend to be Lacey’s boyfriend for a night. At dinner, Lacey’s parents give their blessing and promise that if Lacey and Patrick were to marry, they would give them one million dollars as a gift. Patrick is struggling with money issues and immediately proposes to Lacey, who accepts just as quickly. Meanwhile, Sam keeps hitting animals with the car, and Ed and Martin become temporarily famous when a video of them goes viral.

Jennifer announces that the woman (Gina Gershon) to whom Charlie lost his virginity in high school (while Charlie and Jen were dating) is in town. Charlie goes to see her, and she remembers aloud that it was so quick, she’s "not even sure it counted." This makes Charlie determined to sleep with the woman again as a "do-over", but he must initiate a series of favors to make it happen. Meanwhile, Lacey’s parents have to stay at her and Patrick’s place for a few days, complicating their marriage ruse, especially when Patrick’s boyfriend shows up.

Charlie and Jordan are interviewed by a reporter named Vanessa (Kim Shaw), who is writing about their sex study. Jordan leaves early, and Vanessa convinces Charlie that she should ’test out’ the sex machine with him to be able to write an informed report. The test results show that Vanessa is in love with Charlie, which both Jordan and Charlie think is a mistake that would mean the machine is broken. Charlie tries to convince Vanessa that she really is in love with him, to keep her from writing a report saying that their research is faulty. But he soon discovers that Vanessa is actually the girl that gets him coffee at McDonald’s every morning (not a reporter), and that she is, in fact, madly in love with him. Meanwhile, Nolan gets a job at a lingerie store, which leads to Lacey and Jen taking advantage of his employee discount.

Lacey gets sentenced to house arrest and moves in with Charlie. After intentionally ruining two of Charlie’s dates, Lacey reveals she’s upset that Charlie never hit on her while she was there. Meanwhile, Sean plays wingman to help Michael get laid.

Sasha (Anna Hutchison), a hooker from Charlie’s past, returns with an offer for Charlie for the two of them to sail a yacht to Hawaii as a favor for her friend, but they have to leave on Christmas eve and he has already invited his therapy group for a get-together that evening. Elsewhere, Sean misinterprets Jordan’s intentions when she intentionally drives away his date and then invites him over to decorate her Christmas tree, while Ed steals a Mexican-looking baby Jesus from a local church’s Nativity scene.

While at his bank wearing only a T-shirt and pajama bottoms (sans underwear), Charlie becomes outraged over bank policies and fees and pulls his pants down. After spending a night in jail, he learns that the APA may suspend his license. Meanwhile, his patients have been trying to find another therapist after Charlie is frequently tardy and hung over, but they can’t find anyone that measures up. In the end, Charlie has Jordan, Sean and his patients all appear as character witnesses before an APA panel, but only Jordan’s wits (and strategic crying) can save Charlie’s license.

Jordan accompanies Charlie to counsel the prison group. While there, Wayne pulls Charlie aside and explains that he is about to be transferred to a Texas prison, where he has many enemies and is sure to be killed. He proposes that Jordan gets engaged to him, which the prison board will view as a reason to keep him in California. What’s in it for Charlie? If he can convince Jordan to go along with the idea, Wayne will offer him the chance to write his story, for which a publisher has already offered a seven-figure sum. Meanwhile, Lacey doesn’t feel the $100,000 her parents gave her for a wedding ceremony is enough to cover the event plus all her "accessories", so she and Patrick try to double the money in Las Vegas.

Jordan’s twin sister, identical in every way except hair color and the addition of fake boobs, is in town. Jordan tells Charlie that the two don’t get along ever since her sister slept with her former fiancee. She asks Charlie to help mend the damage between them, but he winds up sleeping with the twin. Elsewhere, Lacey’s sister blackmails her into buying her whatever she wants in exchange for not revealing to their parents that the marriage to Patrick is a sham.

When Patrick brings Molly (Masiela Lusha), his friend from Iowa, to Charlie’s house to meet the gang, Lacey and Nolan make a bet over who will sleep with Molly first -- Charlie or Sean. The two guys also make their own bet, then go to great lengths to please Molly and try to get her alone. She eventually says she likes them both and offers a three-way, but that goes by the wayside when she begins to think that Charlie and Sean are a gay couple. Meanwhile, Jordan asks Patrick to sing with her on an original song at her AA group’s annual talent show.

Eugene Alvarez (Eugenio Derbez), a drinking buddy from Charlie’s past, is now a novice priest performing the wedding ceremony for Lacey and Patrick. Charlie is convinced his friend made a mistake, and he tries to tempt him with booze and hookers before remembering Eugene always had the hots for Jennifer. Meanwhile, Lacey and Patrick are a day away from their wedding when "Fat Mahesh", the man from India Lacey was arranged to marry, shows up for the rehearsal dinner -- only he’s now slim, handsome and rich.

Ed and Martin ask Charlie to help them deal with their loud Latin neighbors, whom Ed assumes are Mexican but are actually from El Salvador. When Charlie arrives, he meets a hot Latina woman and sleeps with her, despite finding out she is leading the charge to get Ed and Martin evicted from their apartment.

Charlie has office sex with the receptionist while waiting to see his APA probation officer, then later finds out the woman is his probation officer’s daughter and that she obsesses over any man who sleeps with her. Acting on advice from his prison therapy group, Charlie uses Jennifer in a ruse to get the woman to leave him.

Charlie wants to date a beautiful woman named Holly, but she tells him she’ll only do so if he gets good ratings on "Lizzy", a internet site where women can rate the men they date. In order to get one, Charlie goes on a fake date with Jordan, whom he then leaves because Holly is there as well. Thus, Jordan gives him a bad rating. Charlie changes the review when Jordan is in the bathroom and gets a date with Holly, which is ruined when Jordan confronts him. Meanwhile, Ed dates Nolan’s mother and teaches him how to ride a bike.

When the sex study ends and a publisher is interested, Jordan finds that the publishing offer is from Maxim magazine. As she was hoping for the study to wind up in a respected medical journal, Jordan rejects Maxim’s offer, to the dismay of both Charlie and a rep from the university. Charlie later has an idea to use his skills helping prisoners re-enter society, but is told that adding a woman gives him a better chance to get funding. After not finding a suitable female partner, he turns to a now-drunk Jordan and receives a non-answer. Meanwhile, Lacey is homeless after her parents cut her off, and is tricked by Nolan into moving into the apartment next to his.

Charlie, not realizing the time of day, is caught by his therapy group having sex with his girlfriend Sasha (Anna Hutchison). When his continued relationship with Sasha makes him late for work, Jordan is left to attend a sexual harassment seminar at the prison alone. Jordan then decides to interfere with Charlie’s sex life with Sasha by convincing Sasha to refrain from having sex for six months as a "cleanse," telling her that she is doing the same. Upset by Jordan’s meddling, Charlie convinces Sasha that Jordan was lying and that what they were doing together is fine. Meanwhile, Ed, Patrick and Nolan decide to renovate Lacey’s apartment after earlier hearing her complain.

Charlie proclaims Jordan ready to handle a prisoner counseling session on her own, mainly because he wants to attend a "stripper bus" party for Sean’s birthday. While counseling a handsome prisoner named Tim, a nervous (and slightly drunk) Jordan makes out with him. Facing the prospect of losing their program, Charlie meets with Tim to ask for his silence, but is blackmailed. Charlie then asks Wayne if he can talk to Tim. Charlie and Jordan freak out the next day when they hear that Tim "fell" to his death from the roof of the administration building. Elsewhere, Sean offers to model clothing for Patrick to help the latter make a video audition for a fashion-themed reality show.

Lacey is determined to kill her ex-boyfriend, who she shot in the testicles, upon learning that he is getting married, so Charlie has to spend the night with her to try and keep her anger in check. Meanwhile, Jordan takes care of Sean when he catches a nasty flu, then catches the flu herself. The two later have cough syrup-induced sex.

After Charlie and Jordan counsel a prisoner who is close to being released, the prisoner gives Charlie a rat-tooth necklace that he made and asks him to deliver it to his girlfriend. Charlie does so, but the woman says she plans to leave her boyfriend and offers Charlie sex. Just before being released early, the prisoner finds out his girlfriend cheated and is leaving him, causing Charlie to find a scapegoat. Meanwhile, Charlie’s therapy group members all try to give up something they love for 24 hours, but all soon fail.

After a night of passion with a woman that turns out to be a cop, Charlie’s fear of authority figures resurfaces when he rides along with her on the job and sees her manhandle a perp. Meanwhile, Jordan and Sean reflect on their recent hookup, and spend the next few days trying to figure out if they can have a casual sex relationship.

A prisoner named Jack, doing time for B & E, theft and gun charges, is in his final counseling session with Charlie and Jordan before being released. Charlie expresses confidence that Jack will be able to successfully re-enter society, but is then reluctant to hire him to do some plumbing work. Though he does hire Jack, Charlie follows him everywhere, and later worries that Lacey is using him to break into her ex-boyfriend’s apartment. Elsewhere, Patrick schemes to use Nolan to reverse his fortunes on his fashion design reality show.

Following an argument with Martin, Charlie is convinced the root of his therapy group’s anger lies in their relationships with their parents. He secretly invites a parent of each member (Lacy’s mother, Ed’s surprisingly-still-alive mother, Nolan’s deadbeat father, and Patrick’s "father") to the next session, and tries to get each pair to discuss their issues. Elsewhere, Jordan is determined to have sex with Sean in a public place.

Sean’s sister, an artist named Lauren (Aly Michalka), arrives in town, and Sean strictly forbids Charlie from sleeping with her. Lauren tempts Charlie, but he refuses sex because of his promise to Sean. To get back at Sean for trying to run her life, Lauren paints a portrait of her and Charlie having sex, causing Charlie to try and buy the painting before Sean sees it. Elsewhere, Patrick and Lacey are convinced they picked up the same bisexual guy in a club and they compete for his affections, until they realize he has a twin.

Charlie and Sasha are hitting it off again, and Sasha suggests a threesome with a friend and fellow hooker, Jenna (Tiffany Dupont). After the act, things get complicated when Jenna reveals she only agreed to the threesome to get Sasha to fall in love with her. Meanwhile, a broke Lacey wants to sell some of her eggs, and she uses Jordan’s resume as her own to enhance her profile.

Sean tells Charlie some ideas for boosting revenues at the strip club he manages, and Charlie shares them with one of the club’s dancers after sleeping with her. When he hears that the dancer took Sean’s manager job, Charlie tries to avoid Sean but his friend finds out from Nolan. Charlie goes to the club’s owner to explain the ideas were really Sean’s, only to find that the owner fired Sean for sleeping with multiple dancers. Elsewhere, Lacey joins an AA group for the purpose of wooing a millionaire she knows will be at a local meeting, but Jordan shows up at the same meeting and complicates things.

Charlie learns he will be counseling Will (John Witherspoon), a convicted murderer who had served 50 years in prison but has just been declared innocent based on DNA evidence. A hot reporter from the New York Times seduces Charlie into getting her an exclusive interview with Will, but Charlie senses trouble when Will angrily blames the press for convicting him in the media and preventing a fair trial back in 1964. Elsewhere, Jordan goes to great lengths to prove she is not falling for Sean as a boyfriend.

Ed shares an anger issue during therapy about a "psychic" marriage counselor who took a bunch of his money at a retreat, but did nothing to help bring his wife back to him. Charlie says he’ll go to the retreat to document fraud by the counselor, Dr. Randy (Michael Gross), and get the man’s license revoked. Jordan reluctantly agrees to play the part of Charlie’s estranged wife, forcing the two to share a room and one double bed. Sean makes a surprise visit to see Jordan, assuming she has her own room, and Charlie discovers their relationship. Meanwhile, Nolan meets Kwame, an African man whom he sponsored through a hunger relief fund when Nolan was 8 years old. The all-grown-up Kwame has become highly successful, causing Nolan to lament his own, pathetic life.

Jordan confides in Charlie that she isn’t sure where her relationship with Sean is heading, and that they may have to break up. Meanwhile, Charlie is trying to convince an APA rep named Susie to make him and Jordan the keynote speakers at an upcoming convention. After Sean complains that Jordan hasn’t answered his texts for two days, Charlie tells him that Jordan plans to end things between the two. Seeing that Susie is smitten with Sean, Charlie pimps out his friend to close the keynote deal. But Jordan finds out and gets drunk, ruining their speech. Elsewhere, Lacey has set up a "hot Indian girl in a coma" live Web feed to raise "donations", and the gang berates her for stealing the idea from a Pakistani woman who really is in a coma.

Charlie learns that his anger therapy sessions at the prison will be cut, so he goes to see Warden McClasky only to find that he is retired and has been replaced by a hot woman, Warden Hartley (Elaine Hendrix). Hartley plans to run for state attorney general, and feels that allowing hardened criminals a chance to vent their feelings could be perceived as a waste of money. Fearing their prisoner re-entry program might also be cut, Jordan urges Charlie to resist sleeping with Hartley, but he does anyway. Meanwhile, Nolan is doing well in his new job as a limo driver, and offers to take Lacey, Patrick and Ed for a ride. He gets a call from his client, Quinn (Ethan Erickson), during the ride. Quinn falls for Lacey, which upsets Nolan who now has to drive them on a date the next night.

Nolan wins a free phone, which the others want too. But it turns out to be a sting operation for unpaid parking tickets. Charlie learns from Warden Hartley that she once did a porn scene, and wants to try to use this to get his group financed again. But after having told the prisoners, Hartley tells him that as long as her secret is safe, the group will be financed. So Charlie has to fulfill the prisoners’ wishes in order to keep them quiet. In taking care of Dr. Randy’s wish list, Charlie inadvertently helps him in an escape attempt.

After having firebombed a garbage truck, Charlie is suspended as a therapist and has to attend anger management therapy himself. While at his session, he meets a hot woman named Jane whom he can only date if he can convince her he has no anger problem. Jordan pays some people to make Charlie angry, hoping to convince him that he needs to take his therapy seriously. This gets Charlie in trouble with a man from the APA Ethics committee, whom he assumes is one of Jordan’s plants. In the end, they all attend an anger management session.

Charlie’s garbage man Jimmy (Will Sasso) dumps trash in front of Charlie’s house because he overfilled. This starts a war between them, with Jimmy trashing Charlie’s whole house after Charlie went out with his ex-girlfriend (Arden Myrin) and Charlie later throwing a firebomb at the garbage truck. Meanwhile, Lacey and Nolan compete to become the new building manager in order to live rent-free. After Lacey gets the job, Nolan finds another way to make money.

While Charlie is being harassed by Warden Hartley, Sean and Jordan are thinking of moving in together. To find out if she can trust Sean, Jordan hires a private investigator to follow him. Assuming the hot female P.I. was hired by the Warden to go after him, Charlie pays the P.I. more to spy on "her employer", thinking it’s the Warden. The P.I. finds out that Jordan steals a lot of office supplies, which causes the Warden to fire Jordan. Charlie finds a loophole to help Jordan keep her job, by pretending she’s a heroin addict. Meanwhile, Nolan sublets his apartment to make some extra cash, and lives in his limo for eight days. When Lacey can’t stand the noise the new tenant makes, she moves into the limo with Nolan.

Lacey is dating Tiffer, a music producer, who plans to take her to the MTV Video Music Awards. Patrick discovers Tiffer is cheating, but hides it from Lacey so that the two will wear clothes he designed on the red carpet. After Nolan tells her about Patrick’s deception, Lacey claims on camera that her dress is a Versace. Meanwhile, Charlie meets Kelly, Jordan’s sorority sister who claims no man has ever left her. Jordan plots to have Kelly sleep with Charlie, knowing he’ll likely never call her again and she can then rub it in her smug friend’s face. Charlie finds out about Jordan’s plans and pretends he wants to stay with Kelly forever, but she is so annoying that Charlie cannot continue the ruse.

Charlie is dating the P.I. who was following Sean, which upsets Jordan because the P.I. almost got her fired. Charlie makes a bet with the P.I. that she cannot catch him cheating. He can only win the bet if he takes a cell phone photo with a girl in a hotel room at 8:00 PM before the P.I. finds out. Charlie wins the bet, with Jordan’s unwilling help, but the P.I. then breaks up with Charlie because...well, he’s too good at cheating. Meanwhile, Nolan enrolls in Patrick’s art class after learning that Lacey will be posing nude for the group.

Monica, the hot nerd who used technology to upend Charlie’s life before, is back and the two are dating again. But he soon regrets his decision after Monica hacks into his PayPal account to buy herself all kinds of gifts "from Charlie". With the help of Ernesto and Cleo at the prison, who introduce Charlie to a renowned but "dangerous" hacker named Vlad, he is finally able to rid himself of Monica’s control. Elsewhere, to get back at another girl who "stole her idea" of targeting rich men to date, Lacey schemes to set up the girl with Ed while lying about Ed being wealthy.

After Nolan complains about being bullied at work, Charlie steps in to help him be more assertive. Charlie sets up a ruse where he confronts Nolan’s boss, and has Nolan step in with fake threats. Nolan gains the respect of his coworkers but becomes intoxicated with the power he feels, leaving Charlie to look for a way to turn it off. Elsewhere, Sean and Jordan spice up their sex life with role playing, but Sean is taken aback when one of Jordan’s fantasies is of the two being married with children.

Sasha tells Charlie she has opened a halfway house for hookers trying to get out of the life, but when the home isn’t ready, she pleads with Charlie to open his house to the hookers for a few days. Things go awry when Sean convinces Charlie that a band playing in a local club is the Rolling Stones performing under a pseudonym, and Charlie leaves Jordan in charge so he can join Sean.

Patrick shuns a job interview with Vogue because incidents in his childhood have made him feel like he isn’t good enough. Charlie tricks Patrick into going to his childhood home in Nolan’s limo, but Patrick is afraid to go inside the house until he gets a little "help" from Nolan. Meanwhile, Ed and Lacey scheme to find someone on Craigslist who will beat up Sean for money.

Lacey’s father is in town to tell her that he wants to restart her allowance, but Charlie wants Lacey to learn how to get by on her own. He convinces her dad to tell Lacey that he lost all his money on bad investments. Instead of looking for a job, Lacey hooks up with a rich older man (Gilbert Gottfried) who has made a lot of money developing internet pop-up ads. The guy is so annoying and creepy, Charlie asks Lacey’s father to tell her he has money after all. Meanwhile, Sean is managing another strip club, and offers Nolan a cash kickback for any limo customers he can talk into going there.

After hearing his group’s sad stories about why they’ll be spending Thanksgiving alone, Charlie invites them to have Thanksgiving dinner at his house. Ed had been particularly saddened about not being able to reconnect with his wife, Dorothy, so Charlie secretly invites Dorothy to dinner. But Ed complicates things when he shows up on Thanksgiving Day with a woman he just met the day before. Meanwhile, Jordan is convinced Sean is cheating on her, so she begins hitting on Nolan to make Sean jealous. This in turn makes Lacey jealous when she sees that Nolan is no longer fixated on her.

Sean and Charlie are going on a "guy’s weekend" in Las Vegas, but Sasha shows up just as they are leaving, and Charlie convinces Sean to let her tag along. Following a wild night of partying, Charlie and Sasha discover they got married in a chapel. After first considering getting a quickie annulment, Charlie says he hasn’t felt like staying with a woman until he met Sasha, and wants to give marriage a try. His attitude changes, however, when Sasha’s mother and brother move in. Elsewhere, Nolan and Lacey try to figure out where to go with their relationship.

Charlie is dating an adrenaline junkie who wants him to join her in her latest thrill of sky diving. After Jordan fails to help him cope with the fear of jumping out of a plane, Charlie enlists the help of Nolan who is, surprisingly, a very experienced sky diver. Elsewhere, Lacey decides to use her father’s money to start a high-end shoe business, and she chooses Patrick as her lead designer. However, things don’t go smoothly, and the two end up starting a sweat shop using a Girl Scout troop for labor.

Charlie is approached by a man who wants to franchise the prisoner re-entry clinic to other correction facilities around the country. He is excited about the prospect until he learns that the man is Darren Denby, Jordan’s ex-husband. Meanwhile, Nolan resolves to save the tavern’s tree from being cut down after seeing it has a hummingbird nest with eggs in it. He chains himself to the tree and refuses to leave, even at the expense of missing out on sex with Lacey.

After Charlie misses the rehearsal for Ed and Dottie’s marriage renewal vows due to being out late drinking with Sean, Ed is skeptical that Charlie will make it to the actual ceremony the next day. Charlie promises to be there, but winds up partying with Sean and two girls until 5 A.M. He falls asleep and has numerous weird dreams. When he realizes he is in a dream, he does everything he can to wake himself up. At the prison, Ernesto and Cleo are planning a birthday surprise for Jordan, but Wayne tricks Jordan into thinking they might be planning an escape.

Charlie is dating a woman who works for an online matchmaking service, but she calls it off for professional reasons. She helps match Charlie and Sean with two other women, but shortly into their dates, Charlie is convinced their matches were accidentally reversed. Elsewhere, Jordan agrees to play Juliet in a prison production of Romeo and Juliet.

Ed hosts a poker game and invites Sean over, only to reveal that Sean has been targeted as a "mark" by the rest of the players. Lacey seems to be unhappy in her relationship with Nolan due to his lack of ambition. Charlie tries to help by convincing Nolan to ask for a raise at work, but that backfires and makes things worse.

Lacey pretends to be pregnant in order to scam her rich grandmother, who has promised a priceless ring to her first great-grandchild. But Lacey’s sister Sateen appears to be one step (and a few months) ahead of her. Meanwhile, Martin has met a new woman named Joanne (Cheryl Ladd), and wants her to meet Charlie. Martin forbids Charlie from making advances on Joanne’s "good Catholic daughter" Mary Kathleen (Izabella Miko), which puts Charlie in distress when Mary Kathleen tries to seduce him.

Charlie and Jordan decide they need an assistant who can also act as a swing vote for their many disagreements. Charlie hires Brianne (Emily Montague) after she promises to always side with him. When Brianne starts to side with Jordan after being hired, however, Charlie sets her up with Sean to make Jordan jealous and get Brianne fired. But his actions only make Jordan and Sean realize how much they miss each other. Meanwhile, Nolan gives up pot smoking to get on the good side of Lacey’s parents. Without his daily weed, Nolan becomes a compulsive cleaner with a bundle of energy, both traits that annoy Lacey.

Jordan tells Charlie he is stifling his therapy group’s progress by always intervening when they need help. At the same time, Charlie has an opportunity to work for his old baseball team when they hire a new general manager (Corbin Bernsen) who wants Charlie to serve as the team psychologist. Charlie takes the job and things soon go awry. His therapy group tries to keep him from leaving, Nolan gets arrested, and Jordan becomes overwhelmed at the prison after the state commutes the sentences of a thousand inmates. Charlie finds that the baseball job is not what he expected, while also realizing he needs his therapy patients as much as they need him. Charlie returns to his familiar chair, surrounded by the group, as he asks who wants to go first.