Every Woman That Charlie Harper Dated In Two And A Half Men (2024)

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.

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 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 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 basem*nt 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 join 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.

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.

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."

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.

5 Courtney Leopold/Sylvia Fishman

Played By Jenny McCarthy

Courtney Leopold is first introduced in season 5, episode 9, “Shoes, Hats, Pickle Jar Lids," as the daughter of Evelyn's fiancé Teddy, making her Charlie's soon-to-be stepsister. Despite this, Charlie is immediately attracted to her and ends up sleeping with her despite Alan and his soon-to-be stepfather's objections, which she uses to blackmail Charlie into buying her a Ferrari.

On the night of Evelyn and Teddy's wedding in episode 16, Courtney convinces Charlie she's broke and he offers to lend her $50,000. Charlie proceeds to propose to Courtney from across the aisle right as Evelyn and Teddy exchange vows. In the next episode, Teddy's dead body is found in Charlie's bed, and the investigation uncovers that Courtney and Teddy are actually con artists and lovers, whose real names are Nathan Krunk and Sylvia Fishman. Courtney is arrested and sent to prison, but despite getting duped by her, Charlie tells her he'll wait for her.

Sylvia and Charlie eventually get back together after she gets out of prison in season 8, episode 10, "Ow, Ow, Don't Stop," but end up parting ways two episodes later in "Chocolate Diddlers or My Puppy's Dead." Sylvia attends Charlie's funeral in the season 9 premiere and makes one final appearance three episodes later in “Nine Magic Fingers."

4 Gabrielle

Played By Justine Eyre

At some point between episodes 9 and 10 of season 5, Charlie started dating a French woman named Gabrielle (Justine Eyre). After finding out that Charlie stole his high school girlfriend right before prom twenty years ago, Alan decides to retaliate by stealing Gabrielle away from him.

Alan tries to give Gabrielle back to Charlie out of guilt, but Charlie refuses, failing to mention that he was trying to get rid of her all along. Alan ends up ditching her, too, when he discovers that she just lies motionless during sex, hence the episode title, “Kinda Like Necrophilia.” Gabrielle only makes one other appearance in Two and a Half Men when she appears in Charlie's weed-induced hallucinations in “Gumby with a Pokey."

3 Angie

Played By Susan Blakely

After Courtney is exposed as a con artist and sent to prison in season 5, episode 17, "Fish in a Drawer," Charlie starts dating an older woman named Angie (Susan Blakely), a self-help author he meets at the bookstore, in the following episode. Both Charlie and Alan grow fond of Angie, finding comfort in her warm, nurturing, supportive, maternal disposition.

In the next episode, Charlie's therapist determines that because of their tumultuous upbringing as a result of their mother's cold, toxic parenting, Charlie and Alan view Angie as a surrogate mother whose attention they end up fighting for. Angie introduces Charlie to her son Jeremy's fiancée Tricia, who was once involved with Charlie. Tricia realizes she still has feelings for Charlie and breaks off her engagement with Jeremy, driving him to attempt suicide. Angie blames Charlie and dumps him in a drunken rage.

2 Chelsea Melini

Played By Jennifer Taylor

Of all the women Charlie was involved with in Two and a Half Men, Chelsea was the one he truly loved the most. Charlie and Chelsea had already been dating for a while by the time she made her first appearance in season 6, episode 8, "Pinocchio's Mouth." Their relationship gets more serious as the season goes on, and they even attend couples' counselling with Charlie's therapist in episode 15, "I'd Like to Start with the Cat."

After accidentally confessing that he loves her, Charlie proposes to Chelsea in episode 17, "The 'Ocu' or the 'Pado'?” making her his third fiancée thus far. Charlie's adulterous temptations cause problems in their relationship, but they always manage to work things out. Chelsea moves in with Charlie in season 6, episode 22, "Sir Lancelot's Litter Box," which proves to be a major adjustment for him.

After settling on a wedding date in season 7, episode 7, "Untainted by Filth," Charlie and Alan get drunk together and have a threesome with a woman they met at the bar. Charlie is riddled with guilt about cheating on Chelsea but doesn't tell her about his infidelity. They call off their engagement in season 7, episode 15, "Aye, Aye, Captain Douche," putting Charlie in a depressive state. After hooking up again two episodes later, Chelsea tries to get back together with Charlie until she finds out he slept with her best friend Gail.

Charlie takes a long time to get over Chelsea, who makes a few more appearances in season 7 before leaving his life for good. Chelsea attends Charlie's funeral in the season 9 premiere, where she reveals he gave her chlamydia. She also receives a check and an apology letter from him in part 1 of the series finale. Although his complex dynamic with Rose lasted the whole series, Chelsea was the longest romantic relationship Charlie had on Two and a Half Men.

1 Michelle

Played By Liz Vassey

The last woman Charlie dates before marrying Rose in Paris is a dermatologist named Michelle (Liz Vassey). Charlie and Michelle go on their first date in season 8, episode 6, “Twanging Your Magic Clanger," during which he discovers that she's a few years older than him. He decides this isn't a dealbreaker until he finds himself attracted to her 20-year-old daughter, Shauna. Charlie dumps Michelle to avoid hitting on her daughter, though he claims he's still not over Chelsea. However, when he realizes Shauna does not like older men, he immediately gets back together with Michelle.

When Rose returns in the next episode, "The Crazy B*tch Gazette,” Michelle suspects Charlie actually has feelings for Rose and breaks up with him. This, coupled with Rose getting (fake) married makes Charlie realize he's in love with Rose. Michelle returns once more in the season 9 premiere to attend Charlie's funeral.

Two and a Half Men

TV-14

Comedy

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Two and a Half Men follows the Harper family: Charlie (Charlie Sheen), a womanizing, hedonistic jingle writer who enjoys his lazy lifestyle from the comfort of his large beach house; Alan (Jon Cryer), Charlie's neurotic, far less successful brother; and Jake (Angus T. Jones), Alan's impressionable son. When Alan's marriage falls apart, he moves in with Charlie, much to the older brother's dismay. After bonding with his nephew, Charlie reluctantly embraces Alan's presence, paving the way for one of television's most dysfunctional family environments.

Cast

Charlie Sheen , Jon Cryer , Angus T. Jones , Marin Hinkle , Melanie Lynskey , Holland Taylor , Conchata Ferrell , Ashton Kutcher , Amber Tamblyn

Release Date

September 22, 2003

Seasons

12

Network

CBS

Streaming Service(s)

Peaco*ck

Writers

Chuck Lorre , Jim Patterson , Eddie Gorodetsky , Lee Aronsohn

Directors

James Widdoes

Showrunner

Chuck Lorre

Creator(s)

Chuck Lorre , Lee Aronsohn