Summary

• Though he slept with a lot more, Charlie Harper properly dated 15 women on Two and a Half Men, some of whom appeared briefly while others had longer runs.
• Rose is the only one of Charlie's girlfriends to appear in every season of Two and a Half Men, though the majority of her appearances are as his stalker as opposed to his love interest.
• Chelsea Melini was Charlie's longest and most serious romantic relationship on the show, lasting multiple seasons and resulting in his third engagement, though they never make it to the altar.

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 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.

This list only includes women Charlie actively dated on Two and a Half Men, not women he had previously dated before the show's timeline.

15 Rose

Played By Melanie Lynskey

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 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.

14 Dolores Pasternak

Played By Missi Pyle (Seasons 2, 7, 9, 12), Alicia Witt (Season 6)

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.

13 Lisa

Played By Denise Richards

Denise Richards, Charlie Sheen's real-life wife at the time, made a few special guest appearances as Charlie's ex-girlfriend Lisa on Two and a Half Men in 2003 and 2004. Charlie and Lisa used to live together before the series began, but they broke up due to Charlie's commitment issues. In season 1, episode 10, “Merry Thanksgiving," Charlie tries to win her back even though she's getting married.

Richards returned as Lisa in season 2, episode 9, “Yes, Monsignor," where she reveals that she is now divorced and has a child. Charlie and Lisa get back together for one day, during which he tries to prove he can be a family man and take care of her kid. However, his commitment issues get in the way again (although he claims the issues are all hers), and they break up.

12 Sherri

Played By Jeri Ryan

Of all of Charlie's girlfriends on Two and a Half Men, Sherri (Jeri Ryan) is the most similar to him. A self-assured expert at playing hard to get and using men for sex, Sherri is essentially the female version of Charlie. He is enamoured with her when they first meet in season 2, episode 5, “Bad News from the Clinic," but gets frazzled when she dismisses him so quickly after sex, realizing that she's beating him at his own game.

Sherri returns later that season in episode 19, "A Low, Guttural Tongue-Flapping Noise," and briefly dates Alan, but Charlie gets in his head about having slept with her first. Sherri is also one of Charlie's many exes who attend his funeral in the season 9 premiere.

11 Isabella

Played By Jodi Lyn O’Keefe

In season 3, episode 6, “Hi, Mr. Horned One," Charlie starts dating Isabella (Jodi Lyn O'Keefe), who turns out to be a Satanist cult member. After attempting to perform a seance with Jake and putting Charlie under her spell (literally), Isabella tries to convince Charlie to her covenant and sell his soul to the devil. She and her "sisters" proceed to drug him in order to use him to produce a prophecy child, but when Charlie awakens and protests, Isabella threatens to put a curse on his "manhood."

Charlie only manages to get rid of Isabella after his mother Evelyn, who does Pilates with Isabella, makes her leave him alone. Isabella returns as one of the many ex-girlfriends Charlie hallucinates in "Gumby with a Pokey." She also attends his funeral in the season 9 premiere, where she reveals that he gave her herpes.

Before playing Isabella, Jodi Lyn O'Keefe made her first appearance on Two and a Half Men in season 2, episode 11, “Last Chance to See Those Tattoos,” as a different character named Gail.

10 Mia

Played By Emmanuelle Vaugier

The first of Charlie's four fiancées in Two and a Half Men is Mia (Emmanuelle Vaugier), a dance teacher he meets at a cafe in season 3, episode 8, “That Voodoo That I Do Do." Though she doesn't initially show interest, Mia and Charlie grow closer after he signs Jake up for dance lessons with her.

Mia becomes Charlie's first serious girlfriend on the show, and he struggles to let go of his womanizing ways. She breaks up with him for the first time in episode 13, “Humiliation is a Visual Medium," when he asks permission to sleep with someone else since they're not having sex, but they eventually get back together.

Before the ceremony, Mia tells Charlie he'll have to kick Alan and Jake out of his house to make room for a nursery, but he refuses and calls off the wedding.

After their second breakup in episode 15, "My Tongue Is Meat," Mia is not seen again until the penultimate episode of season 3, when she returns to Malibu and asks Charlie to donate his sperm so she can have a baby. Instead, he proposes to Mia and she says yes. After an argument between their families in the season finale, Mia and Charlie decide to elope to Vegas. However, before the ceremony, Mia tells Charlie he'll have to kick Alan and Jake out of his house to make room for a nursery, but he refuses and calls off the wedding.

From that point on, Mia made sporadic appearances throughout seasons 5-7, including in Charlie's weed-induced hallucination in “Gumby with a Pokey.” Mia also attends Charlie's funeral in the season 9 premiere and is shown receiving a check and an apology letter from Charlie in the series finale.

9 Kandi

Played By April Bowlby

Kandi (April Bowlby) is first introduced in season 3, episode 9, "Madame and Her Special Friend," as Kimber, a ditzy 22-year-old Charlie is sleeping with. She was renamed Kandi upon her return in episode 13, “Humiliation is a Visual Medium," when Charlie hits her up again after Mia dumps him for the first time. When Charlie and Mia make up, Kandi turns to Alan for comfort, and they start a relationship. When Charlie and Mia call off their Vegas wedding in the season 3 finale, Alan and Kandi decide to get married instead.

After she and Alan get divorced in season 4, Kandi doesn't return again until season 10, where she makes a one-off appearance in episode 9, "I Scream When I Pee." Kandi's final appearance is in the series finale, when Alan, knowing that his days are numbered now that Charlie's escaped Rose's dungeon, calls Kandi and tells her she is the love of his life (which he also told his other ex-wives).

8 Lydia

Played By Katherine LaNasa

In season 4, episode 6, “Apologies for the Frivolity," Charlie begins dating a woman named Lydia (Katherine LaNasa), who acts and dresses exactly like his mother, Evelyn. This is blatantly obvious to everyone but Charlie, who insists she's nothing like Evelyn. He only begins to notice the similarities between his mother and girlfriend when he witnesses Lydia treat her sons the way Evelyn treats Charlie and Alan. Charlie vows to break it off but finds he is too attracted to her to go through with it, and they continue dating.

Lydia makes her next appearance later that season in episode 10, "Kissing Abraham Lincoln," in which she bosses Berta around so much she threatens to quit. Charlie pretends to break up with Lydia so Berta won't leave but continues dating her in secret. He only cuts the Oedipal cord for good after Berta finds out he lied and quits on the spot. Lydia returns as one of the many ex-girlfriends Charlie hallucinates in "Gumby with a Pokey" and in the season 9 premiere to attend Charlie's funeral.

7 Chloe

Played By Rachel Cannon

In season 4, episode 23, “Anteaters. They're Just Crazy-Lookin’,” Charlie tries to get rid of his clingy new girlfriend, Chloe (Rachel Cannon), whom he met at an animal shelter. However, he gets jealous when she shows interest in the good-looking handyman Fernando (Enrique Iglesias) fixing his deck, and tries to win her back. Charlie eventually succeeds by buying her fancy jewelry, though she does not appear on the show again except in Charlie’s hallucination in “Gumby with a Pokey."

Before playing Chloe, Rachel Cannon made her first appearance on Two and a Half Men in season 4, episode 9, “Corey's Been Dead for an Hour” as a character named Nina.

6 Linda Harris

Played By Ming-Na Wen

Charlie's first girlfriend in season 5 of Two and a Half Men is Judge Linda Harris (Ming-Na Wen), though they don't hit it off right away. Charlie first meets Linda when Alan sets them up on a double date in an attempt to help him meet more respectable women his own age. However, Linda shows no interest in him due to his immature antics. As a result, Charlie becomes obsessed with winning Linda over and eventually succeeds after deliberately getting sent to her courtroom for a DUI.

Charlie and Linda proceed to date for the next three episodes, until she dumps him in episode 6, "Help Daddy Find His Toenail" after he accidentally got high at her awards ceremony, leading to a photo of him licking her face getting printed in the newspaper. Linda's only other appearance was in “Gumby with a Pokey” as one of the many ex-girlfriends Charlie hallucinates while high.