With the wedding between Evelyn and Teddy just around the corner, Courtney becomes infuriated when she learns that Teddy refuses to make Evelyn sign a pre-nup. Though she is finally on good terms with Evelyn, she tells Charlie that she no longer wants to see him, making Charlie want her even more. He resorts to stalking her outside her apartment with help from Rose. Courtney eventually takes Charlie back after he saves her from being financially cut off by Teddy. During the wedding, Charlie asks Courtney to marry him and she says yes. Alan becomes the ultimate fussy wedding planner.
Congratulations!
The show's 100th episode ("City of Great Racks") aired on October 15, 2007. To celebrate this, a casino-inspired party was held at West Hollywood's Pacific Design Center. Warner Brothers Television also distributed blue Micargi Rover bicycles adorned with the Two and a Half Men logo along with the words 100 Episodes. Each bicycle came with a note saying "You've made us very proud. Here's to a long ride together." The cast also gifted the crew with sterling silver key rings from Tiffany & Co, the key rings were attached to small pendants with 100 and Two and a Half Men inscribed on either side of it.
Monday, April 28, 2008
"Look at Me, Mommy, I'm Pretty" - Season 5
With the wedding between Evelyn and Teddy just around the corner, Courtney becomes infuriated when she learns that Teddy refuses to make Evelyn sign a pre-nup. Though she is finally on good terms with Evelyn, she tells Charlie that she no longer wants to see him, making Charlie want her even more. He resorts to stalking her outside her apartment with help from Rose. Courtney eventually takes Charlie back after he saves her from being financially cut off by Teddy. During the wedding, Charlie asks Courtney to marry him and she says yes. Alan becomes the ultimate fussy wedding planner.
Monday, April 21, 2008
"Rough Night in Hump Junction" - Season 5

Charlie continues to expand his female conquests with two to three girls a day, landing him to even more trouble. After getting beat up by two angry husbands, getting arrested for solicitation, and hurting himself while in the bedroom, he goes to his psychiatrist, Dr. Freedman. She learns that Charlie is feeling lost because his ex-fiancé Mia (Emanuelle Vaugier) is getting married. Charlie attempts to grieve but to no avail, so he decides to go after Mia.
Monday, April 14, 2008
"Winky-Dink Time" - Season 5

While at the coffee shop Charlie recognizes a woman he dated but can’t for the life of him remember her name. Jake falls head over heals for her teenager daughter and proceeds to bug Charlie until he agrees to set up a date. Charlie can’t remember this woman’s name but sets up a double date anyway. At the date Charlie still can’t remember her name. Alan is so lonely since his breakup with Donna that he decides to hire a hooker.
Monday, March 31, 2008
"The Soil is Moist" - Season 5
Alan runs into Cynthia, a mutual friend of he and Judith from back when they were married. Cynthia is recently divorced and Charlie gets that vibe that Cynthia might be interested in Alan. However, Alan is unsure about asking Cynthia out because he knows she's still really good friends with Judith. He gets Judith's blessing and sets up a date with Cynthia. Charlie tells Alan that he is so going to get laid tonight� "You've been friends for years, what more do you need to establish? You best bring your "A" game because you know she's going to go back and tell Judith about it."Pre-sex and in bed Alan is really worried and starts seeing images of Judith sitting on the chair next to them in bed. Alan does his best and Cynthia is more than satisfied. He asks Cynthia to tell Judith that he was remarkable in bed. The next day in his kitchen he debriefs Charlie on last night's events but seems a little distracted, almost bummed out. He's being seeing visuals of Judith and Herb making love and Herb is better than Alan ever was with Judith. While on a date with Cynthia, Alan keeps on questioning her about what Judith says about her lovemaking with Herb. What makes him so good? Annoyed, Cynthia dumps Alan claiming that he still has feelings for Judith.
Monday, March 24, 2008
"A Little Clammy and None Too Fresh" - Season 5
Charlie catches a cold after he knowingly sleeps with a hot girl who is sick. Alan and Jake are on their way out and can't take care of Charlie. Berta can't be bothered. Desperate, Charlie calls his mom who is also unavailable. We see Rose, who was asked to leave England, climb over the deck. She steps up to the task and takes care of Charlie. Montage of Rose making Charlie soup, giving him a "special" pill that was just approved in England, cleaning him, bathing him, shaving him, dressing him. Rose makes sure he doesn't get out bed. Feeling a bit better Charlie gets himself up and makes it downstairs only to discover that he's been in bed for two weeks. Alan and Jake think it's great that Rose is taking care of him and they head out.We go back upstairs and Rose is in the shower... we also see her clothes now neatly hanging in Charlie's closet. She comes out of the bathroom and tells him he needs to be back in bed sleeping and makes him take another pill. Charlie pretends to take the pill and go to sleep. After Rose leaves the room (she locks Charlie in) he takes the pill out and puts it under his pillow. He then proceeds to climb out the window down into Alan's bathroom (Alan is sitting on the toilet). Charlie tells Alan that he thinks Rose has been drugging him and he'll take him upstairs to show him the pill. We go upstairs and we see Berta out cold on Charlie's bed. Charlie has no proof.
Monday, March 17, 2008
"Meander to Your Dander" - Season 5
Charlie offers up breakup advice when Alan admits that his relationship with Donna has become boring and the sex mundane. Alan takes his advice and breaks up with Donna, only to soon learn that she felt the same way about the relationship and wanted to take the relationship to the next level. Alan is relieved until he discovers that Donna meant taking the relationship to the next level by having a threesome.Meanwhile, Charlie takes Jake to a pizza joint and notices that Jake has been eyeing a girl who is eating pizza with her mom. Charlie unsuccessfully attempts to charm mom into letting Jake come over and meet her daughter. Charlie persists and gets pepper sprayed by the mom, and Jake and the girl have a moment.
Monday, November 26, 2007
"Kinda Like Necrophilia" - Season 5
When Jake is dumped by a girl for the first time, Alan tries to make him feel better by talking about the first time he was dumped. It was in high school and the girl, Charity, dumped him the night before a big dance. Charlie's advice to Jake is to find the prettiest girl, because the prettiest ones are the loneliest, and ask her out because all the other guys will be afraid to.
Later, Alan has a drink or two and starts reminiscing about Charity and wonders why she dumped him. He pulls out his old year book and decides to call her. Charlie tells him nothing good can come from drunk dialing an old girlfriend.
Alan reaches Charity on the phone and asks her why she dumped him right before the dance. She tells him to ask his brother.
The next day, Jake takes Charlie's advice and asks out a pretty girl. It works: she says yes. Meanwhile, Alan can't stop giving Charlie a hard time about stealing Charity, but Charlie doesn't think twice about it and leaves.
Gabrielle, Charlie's current flame, drops by looking for Charlie who hasn't been answering his phone. Alan seizes the opportunity to bond with her emotionally and they set up a date. Charlie comes home and sees the two of them hitting it off on the porch.
He puts a horrible guilt trip on Alan, but eventually says that he should continue dating Gabrielle. A vindicated Alan goes out with Gabrielle, but when things become intimate she lies on her bed like a robot and tells him to get it over with.
Alan realizes that Charlie wanted to get rid of Gabrielle all along and had him do his dirty work.
Making matters even worse for Alan, Charlie connects with ex-girlfriend Charity a second time.
Monday, November 19, 2007
"Shoes, Hats, Pickle Jar Lids (aka Tight's Good)" - Season 5
Teddy and Evelyn have gotten engaged and Charlie and Alan are miserably bored at their engagement party.
Teddy's daughter Courtney soon arrives - who Evelyn doesn't get along with - but, who Charlie is instantly attracted to.
Teddy warns Charlie to stay away from his daughter. Courtney sells high-end cars and she sets up an appointment for Charlie to check out her cars.
While showing Charlie the Ferrari, Courtney is clearly hitting on him but Charlie is trying to honor Teddy's wishes and hesitantly turns her down.
The next day Courtney drops by the house with keys to a Bentley that she wants Charlie to test drive. Still hitting on Charlie, Jenny asks him what he's got to lose and seconds later, they end up in bed. Later, Teddy and Evelyn come over to ask Charlie if they can have the wedding at Charlie's house.
Charlie tells Courtney to make herself scarce and not come downstairs while he deals with Teddy and Evelyn. When Teddy asks Charlie and Alan if they would do the honor and stand up for him at the wedding, music blares from upstairs and Charlie panics. Charlie bolts upstairs and Courtney tells him she was bored and wanted to listen to music. He temporarily gets her to be quiet only to have her blast the music again when he goes back downstairs.
Frantic, he runs back upstairs and asks her what it's going to take to shut her up so he can go downstairs and deal with Teddy and Evelyn. There's only one thing she wants: for Charlie to buy that Ferrari. He caves. On his way out, Teddy (who knew Courtney was there all along), tells Charlie he warned him about staying away from his daughter: she's a sociopath.
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