"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.