Charlie Harper dated a lot of different women until his (fake) death in Two and a Half Men and even got engaged to a few of them. Over the course of the first eight seasons, before Charlie Sheen was fired and replaced by Ashton Kutcher, his character was notorious for his endless string of one-night stands. Charlie only properly dated a fraction of the women he slept with, and was involved in serious, committed relationships with even fewer. Given his track record, though, this still adds up to a decent amount.
In total, Charlie had 15 actual girlfriends on the show, though some of these relationships lasted longer than others. Most of Charlie’s girlfriends in Two and a Half Men only appeared in a few episodes before he kicked them to the curb (or vice versa), but a couple of them had lengthy runs on the show. Following Sheen’s departure from Two and a Half Men, many of Charlie’s exes attended his funeral in the season 9 premiere. Some even returned in the series finale, where it was revealed that Charlie was still alive.
Although they wouldn’t actually be together for some time after her introduction in the pilot episode, Rose (Melanie Lynskey) was the first of Charlie’s eventual girlfriends to appear in Two and a Half Men. After their one-night stand before the events of the series, Rose became obsessed with Charlie and started stalking him. Rose also happens to be Charlie’s neighbor and often climbs over the balcony of his beach house to pay him a visit.
In season 5, Charlie becomes convinced that he’s in love with Rose and confesses his feelings, but when Rose tells him she wants to settle down with him, he flees the scene. After this, Rose’s appearances became more sporadic in the latter half of the show, though she does appear in every season of Two and a Half Men. After Rose stages a wedding with a mannequin in season 8, episode 7, “The Crazy B*tch Gazette,” to make Charlie jealous, they begin having an “affair” which culminates in a weekend getaway to Paris where Charlie plans to propose.
[In] the series finale…she confesses that Charlie is actually alive and has been trapped in a dungeon in her basement all this time.
In the season 9 premiere, Rose claims that she caught Charlie cheating after they got engaged but decided to forgive him. The next day, Charlie “accidentally” died in a train accident, though it is heavily implied that she killed him. Rose maintains this story for four years until the series finale, when she confesses that Charlie is actually alive and has been trapped in a dungeon in her basement all this time. In total, Rose appeared in 63 episodes of Two and a Half Men and was the only one of Charlie’s love interests to appear in all 12 seasons.
Dolores Pasternak
Dolores Pasternak was first introduced as Jake’s teacher in season 2, episode 3, “A Bag Full of Jawea,” where she was played by Missi Pyle. When Jake gets suspended for flipping her off, Charlie starts dating Miss Pasternak in hopes of lifting his nephew’s suspension. She starts giving Jake good grades and special treatment, but Charlie ultimately breaks up with her because she is mentally unstable.
Dolores doesn’t appear again until season 6, episode 5, “A Jock Strap in Hell” (now played by Alicia Witt), where it is revealed that she lost her teaching license and has been living in a motel and working as a stripper. When the Harpers take her in, Dolores finds God and falls for Charlie all over again. He ends up dumping her again, which causes her to revert to her old ways.
Missi Pyle reprised the role of Dolores in the character’s last three appearances, the first of which was in season 7, episode 21, “Gumby with a Pokey,” when Charlie is visited by the ghosts of his ex-girlfriends during a weed-induced hallucination. Dolores also attends Charlie’s funeral in the season 9 finale and receives a check and apology letter from him in part one of the series finale.
