All women that Charlie Harper dated in Two And A Half Men, dating history revealed

Two and a Half Men is a sitcom that aired from 2003 to 2015. It’s about Charlie Harper (played by Charlie Sheen), a rich and carefree man living in Malibu, who writes jingles for a living. His life changes when his brother Alan and nephew Jake move in with him. Charlie is known for dating many women. He was not the type to settle down and always liked to have fun. His love life was one of the most hilarious and interesting parts of Two and a Half Men.

Let’s take a closer look at all the women Charlie dated in Two and a Half Men, how their relationships started, and why they ended.

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Charlie Harper's dating history in Two and a Half Men

Rose

Rose (played by Melanie Lynskey) was Charlie’s neighbor and one of the first women we saw him with in Two and a Half Men. She appeared in the first episode and became obsessed with him after a one-night stand. Charlie broke up with her, but she kept showing up and even stalked him. Later, they got back together, and in the final season, it was revealed Rose kept him locked up after everyone believed he was dead.

Lisa

Lisa (played by Denise Richards) was Charlie’s girlfriend before the events of Two and a Half Men season 1. They had broken up due to Charlie’s inability to commit. He tried hard to win her back in season 1, even when she was going to get married. Lisa returned in season two of Two and a Half Men after a divorce (she was also a mother now) and Charlie dates her again but his commitment issues become the reason for their break-up yet again.

Dolores

Dolores Pasternak (played by Missi Pyle / Alicia Witt) was Jake’s teacher and dated Charlie in Two and a Half Men season 2. Charlie thought she was not mentally stable and ended things. She came back in later seasons, once played by Alicia Witt and later again by Missi Pyle, but nothing ever lasted between them.

Sherri

Sherri (played by Jeri Ryan) appeared in season 2 of Two and a Half Men and was one of the few women who treated Charlie the way he treated others. She was smart, independent, and not clingy. Charlie liked her, but he couldn’t handle someone so strong-willed. She returned briefly in Season 5, but nothing really happened between her and Charlie again. She appeared in the funeral episode in season 9.

Isabella

Isabella (played by Jodi Lyn O'Keefe) appeared in season 2 of Two and a Half Men and had a dark, goth style. Charlie found her interesting at first, but after she tried to get him to join her satanic cult and then drugged him, Charlie got scared. Their relationship ended fast, and she was never seen again until the funeral episode.

Mia

Mia (played by Emmanuelle Vaugier) was a dance teacher and one of Charlie’s most serious girlfriends. She first appeared in Two and a Half Men season 3, and Charlie even wanted to change for her. They even got engaged, but she wanted Alan and Jake out of the house so that they could have a nursery for their future child. Charlie refused, and they broke up. Mia returned in later episodes but never dated Charlie again. She last appeared in season 9’s funeral episode.

Kandi

Kandi (played by April Bowlby) was young and pretty, but not very bright. Charlie dated her in season 3, but they didn’t last. Later, she dated Alan and married him for a short time. She came back in Season 10 and appeared in the final episode.

Linda

Linda Harris (played by Ming-Na Wen) was a judge who dated Charlie in Season 5. Charlie and Linda dated for a while, but his immature actions embarrassed her in public. She left him and was not seen except in the hallucination episode.

Lydia

Lydia (played by Katherine LaNasa) was introduced in Two and a Half Men season 4. She had a controlling personality and resembled Charlie’s mother, Evelyn. Charlie pretends to break up with Lydia to prevent Berta from quitting, but when Berta finds out the truth and quits, Charlie has to actually end things with Lydia. We saw her last in the funeral episode, Gumby with a Pokey.

Chloe

Chloe (played by Rachel Cannon) appeared in season 4. Charlie found her clingy and wanted to get rid of her, but then again felt jealous when she gave a handyman attention. He manages to win her over, but she is not seen in the show again except a hallucination scene in Gumby with a Pokey.

Courtney/Sylvia

Courtney Leopold/Sylvia Fishman (played by Jenny McCarthy) first appeared in Two and a Half Men season 5 pretending to be someone else. She conned Charlie into giving her money, then vanished. When she returned in Season 8, Charlie dated her again, but it did not work out. Her real name was Sylvia Fishman, and she last appeared in season 9’s Nine Magic Fingers.

Gabrielle

Gabrielle (Justine Eyre) appeared in season 5. She dated Charlie, but then Alan dated her out of spite as Charlie had stolen one of Alan’s girlfriends in high school. Alan later decides to ‘give her back’ to Charlie, but Charlie did not want her back anyway. Alan finally broke up with her due to s**ual incompatibility. She made a short return in Charlie’s hallucination episode.

Chelsea

Chelsea Melini (played by Jennifer Taylor) was Charlie’s longest serious relationship. She first appeared in Two and a Half Men season 6, and they even got engaged. But Charlie couldn’t stay loyal, and they kept dating on and off until they called off the engagement due to Charlie’s disloyalty. She came back in Season 9 and again in the finale.

Angie

Angie (played by Susan Blakely) first appeared in Two and a Half Men season 5 and was older than most of Charlie’s girlfriends. She was wise and successful, someone who both Charlie and Alan adored, but Charlie got involved with her son’s fiancée. That led to Angie’s son committing suicide, and when Angie found out, she ended the relationship.

Michelle

Michelle (played by Liz Vassey) was a doctor whom Charlie met in Two and a Half Men season 8. Things seemed good until Charlie met her daughter and got interested in her instead. Although he realized Michelle’s daughter was not attracted to older men, he got back together with Michelle. But Michelle then suspected he had feelings for Rose and broke up with him after that, and later came back for Charlie’s funeral.

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Charlie Harper’s dating life in Two and a Half Men was full of funny and crazy moments. He met many women, but none of them could truly change him. Even though his love life was a mess, it gave the show many of its best and funniest moments.

You can stream Two and a Half Men on Amazon Prime Video.