"Waiting for the Right Snapper" - Season 5

Charlie meets with his therapist, Dr. Friedman, and she’s unable to convince him of his mommy issues. Alan is her next appointment and tells her that he has feelings for Angie. He also reveals his plans to steal her from Charlie, eventually declaring an outright war for Angie’s heart. As a response Charlie feels the only way to secure Angie is to sleep with her. He does and it’s absolutely great. Charlie meets Mike’s fiancé, Trisha, and they both realize that they “know” each other. Trisha discovers she still has feelings for Charlie. Later, he shows up at Angie’s house to find her drunk and miserable because her son called off the wedding after finding out that Trisha still has feelings for Charlie. It’s over for Angie and Charlie - and Alan doesn’t even stand a chance.

"If My Hole Could Talk" - Season 5

Jake struggles with a book report assignment by continuing to misplace the book, making Charlie and Alan revisit the bookstore. Charlie goes to the self-help section to figure out why all his relationships continue to fail, when he meets a woman named Angie (Susan Blakely). When they start dating, he struggles with the fact that she’s much older than he is, but he continues to date her anyway, simply because Angie would make a great replacement mom. Alan teases Charlie about the age difference. When Alan finally meets Angie, he’s instantly enamored and he starts having feelings for her. They also meet Angie’s son, Mike, who’s engaged and happens to be 32 years old.

"Fish In A Drawer" - Season 5

Teddy is found dead on Charlie’s bed with his pants around his ankles after his wedding with Evelyn. A CSI team is assembled to find some clues, taking all the guests into custody for questioning. They discover that Teddy and Courtney were actually con artists who had set their sights on Evelyn’s money. In fact, Courtney and Teddy weren’t even related: They were lovers. They celebrated their con after the wedding when Teddy really dies after suffering a heart attack.

George Eads, from "CSI: Crime Scene Investigation," made a cameo appearance, as part of a crossover with writers and an executive producer from "CSI:Crime Scene Investigation."

"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.

"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.

"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.

"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.

"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.

"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.