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Two and a Half Men Season 5 Episodes

19 Episodes 2007 - 2008

Episode 1

Large Birds, Spiders and Mom

Mon, Sep 24, 200721 mins

Charlie is plagued by a terribly and 'intimate' itchy rash (privates is inappropriate for him, as Alan points out). Now Jake is finally allowed to junior high school, Alan 'prepares' him by making him a target of ridicule, not bullying. Alas Alan and Charlie pull out too many horror stories, so Jake finds his own safe 'solution'. Charlie mocks Alan's constant cowardliness, stirring him to a single, soon regretted act of ill-considered bravery.

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Episode 2

Media Room Slash Dungeon

Mon, Oct 1, 200722 mins

Alan walks into Evelyn's trap, so Charlie gets recruited as her male escort instead of spending the evening with his latest girlfriend Mitzi. However, Charlie enjoys learning how she works the high-end real estate market. Alan's night alone with Sharon goes wrong because of her near-suicidal self-image. It gets worse--but not for everyone--when Charlie breaks his promise not to date a top client's adulterous wife.

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Two and a Half Men, Season 5 Episode 2 image

Episode 3

Dum Diddy Dum Diddy Doo

Mon, Oct 8, 200722 mins

Jake becomes an insufferable cellphone-junkie. Tired of meaningless floozies, Charlie decides after a particularly dumb one to double-date with Alan's friend. Charlie nearly freaks out learning that Linda is a municipal judge and law professor. Soon he can't resist the challenge, even if that sets him on a bumpy course for embarrassment.

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Episode 4

City of Great Racks

Mon, Oct 15, 200722 mins

Charlie and Linda get closer to consummating their relationship, but Charlie has trouble focusing when he begins to see Rose's face everywhere he turns: dog walker, bartender and house keeper. Dr. Freeman says that he is only imagining Rose because he is afraid to grow up. Reflecting on that, Charlie ends up on the next flight to London to find out if Rose is still truly there. Charlie does indeed find her and they go out for a drink at the local pub, where she asks for commitment in a relationship, scaring Charlie back to California as he is already in one. After Charlie and Rose leave to the pub, wigs and costumes in her apartment reveal this was part of Rose's scheme.

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Episode 5

Putting Swim Fins on a Cat

Mon, Oct 22, 200722 mins

Going through the bills, Alan panics because Charlie hasn't had a jingle commission in months and admits that business is slow and may not change. Therefore Alan accepts $1,000 a week as a test person for an experimental drug, despite a terrible list of side effects, and soon finds he's not in the control group. Charlie however keeps spending, especially on his latest girlfriend, Linda Harris. Linda brings along her adolescent son Brandon, who proves quite a handful when he agrees to babysit. Charlie's child skills surprise everyone as he pours his artists creativity into the job, such as musical tunes to make the boy eat his food.

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Two and a Half Men, Season 5 Episode 5 image

Episode 6

Help Daddy Find His Toenail

Mon, Oct 29, 200722 mins

Alan refuses to let a 17 year-old mate drive Jake to a rock concert. Yet Evelyn takes their kid's side, which inspires him to sneak out the window. Charlie is angry his bed mate judge Linda didn't tell him about a political award dinner, so he gets invited to attend her big day. Alas, Evelyn accidentally slips him not a tranquilizer but a hallucinogen. It becomes a weird night for everyone, including Jake, whom he tries to help sneaking back in, and Alan who catches them.

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Two and a Half Men, Season 5 Episode 6 image

Episode 7

Our Leather Gear Is in the Guest Room

Mon, Nov 5, 200721 mins

Alan's arrogant decision to place a cheap, flashy bowl he bought in a prominent place is the last straw for Charlie, who reminds him of his place as the guest. Alan claims it wasn't a home until he and Jake moved in. He leaves, but has nowhere to go and lands at Evelyn's door. She doesn't want an audience while she plays love games with Teddy, so the unwilling host tries lies and worse to reunite the brothers.

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Two and a Half Men, Season 5 Episode 7 image

Episode 8

Is There a Mrs. Waffles?

Mon, Nov 12, 200720 mins

Alan and Jake hardly take notice of Charlie's success on TV as singing children's idol "Charlie Waffles", but a flow of fat checks awakens fraternal envy. Yet, when manager Bob "Artie" Pliskin enforces the contract to make Charlie do the one thing he fears, performing in front of an audience, Alan supports him, only to become jealous again after seeing that even a drunk Charlie's partially scatological repertoire scores with his adoring audience.

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Two and a Half Men, Season 5 Episode 8 image

Episode 9

Tight's Good

Mon, Nov 19, 200721 mins

At ma Evelyn's engagement party, her fiancé Teddy makes Charlie promise to stay away from his foxy daughter, wicked luxury car salesperson Courtney. However that vixen successfully seduces and screws Charlie, for a change - and for a fair fortune.

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Episode 10

Kinda Like Necrophilia

Mon, Nov 26, 200722 mins

Charlie's French latest conquest, Gabrielle, makes Alan hornily jealous. So he desperately calls Charity, who dumped him on his prom night, only to learn that it was for Charlie. Jake also was just dumped. Charlie tastes sweet revenge when Gabby dumps Alan for him, but soon gets a bitter aftertaste, with worse to come.

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Episode 11

Meander to Your Dander

Mon, Mar 17, 200822 mins

Jake's overt shallowness is insufferable even for Charlie, and taking him along to a restaurant as diversion proves a painful mistake. Alan can only admit he and his latest bedmate have overstayed their sexual interest to his brother. He takes the master's advice on how to dump himself, aware of risks. He dodges them all except an accidental hot coffee pouring were it hurts most, but ends up the looser and feels hurt even worse when a surprising third party arrives.

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Episode 12

A Little Clammy and None Too Fresh

Mon, Mar 24, 200822 mins

Charlie has a killer cold and is feeling miserable but nobody comes to take care of him, until Rose comes back from England. However, Rose talks about eternal care, gives him her pills, and clearly enjoys nursing him entirely too much. After two weeks he feels transformed into a living doll. Meanwhile, Alan feels miserable now that he is the very last person with whom Jake wants to spend time.

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Episode 13

The Soil is Moist

Mon, Mar 31, 200820 mins

Charlie correctly predicts that Cynthia Sullivan, a friend of Judith and Alan while they were married, will even go for Alan. Alas, born loser Alan can't help stressing about her remark that Judith considers Herb her best lover ever, even imagining that the couple are observing his performance.

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Two and a Half Men, Season 5 Episode 13 image

Episode 14

Winky-Dink Time

Mon, Apr 14, 200822 mins

Alan is through with disastrous 'romantic' dates, so he gets Charlie to find him a cheap, but classy, hooker. Jake can only get a date with young Milly by agreeing to a double-date with her mother and reluctant Charlie, who can't even remember the mother's name. Alan's lack of sexual self-confidence wrecks even Alexis' professional routine.

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Two and a Half Men, Season 5 Episode 14 image

Episode 15

Rough Night in Hump Junction

Mon, Apr 21, 200822 mins

Alan points out that Charlie's serial dating is getting excessive, even by his standards. Even bloody noses from angry husbands and sorely overexerted genitals can't slow Charlie down. Dr. Freeman diagnoses the cause as grief because his ex, Mia, whom he actually loved, is getting married. Charlie's response is to try to "get her back", in the bridal suite, before the wedding.

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Episode 16

Look at Me, Mommy, I'm Pretty

Mon, Apr 28, 200822 mins

Alan becomes the wedding planner for Evelyn and Teddy, who waives a prenuptial, while the Harper brothers discover their mother is very rich. Teddy finds Charlie, coached by Rose, stalking Courtney. Rose leaves Charlie behind to stalk Teddy herself. Charlie finds himself comforting Teddy's now-broke daughter, Courtney, who has lost her job. The ceremony goes ahead, with preposterous vows scripted by the fifth-time bride.

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Episode 17

Fish in a Drawer

Mon, May 5, 200821 mins

While Evelyn still enjoys the wedding reception, Charlie finds her latest husband Teddy dead on bed, pants down and skull smashed. He and Alan have no choice but to inform their mother and call the police, which turns the feast into a murder investigation. The Harpers are treated as suspects, but ultimately learn neither Teddy nor his daughter Charlie's potential bride, were who they seemed to be.

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Episode 18

If My Hole Could Talk

Mon, May 12, 200822 mins

Hoping for an earthquake to undo his Shakespeare assignment, Jake left it till the last weekend, without Taming the Shrew. Alan drags him to the bookstore, not that a copy has any chance of actually getting read, however hard he pushes his nitwit son. There Charlie meets and dates mature author Angie, an expert flatterer, who soon 'mothers' the neglected brothers.

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Two and a Half Men, Season 5 Episode 18 image

Episode 19

Waiting for the Right Snapper

Mon, May 19, 200822 mins

Charlie blatantly rejects his cynical claim that his mother issues compromise his unconsummated relationship with otherwise perfect Angie, which is further jeopardized after he meets her adult son Jeremy's fiance Tricia, realizing she is one of his ex-girlfriends, who can't forget him, but he refuses to take her back, yet is blamed when she still calls off the wedding, part of jealous Alan's plan to sabotage Charlie, whose place he fails to take. Meanwhile, Alan tries to get Jake to study for his Algebra exam, but lazy Jake has other ideas, like scoring above the 67% required to pass is 'waste', never mind being a slacker like his doted uncle, whom Angie also blamed for his openly-realistic view on the incorrigible brat.

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Two and a Half Men, Season 5 Episode 19 image