Charlie Harper dated many women in Two and a Half Men, but who of the main character's flames burned the brightest?

Sitcom fans are all familiar with the infamous Charlie Harper on the hit comedy Two and a Half Men. He was one of the show's main characters in the first eight seasons, and throughout these episodes, the womanizer dated plenty of women.

Some of them only lasted a single episode, while others made it longer. Of course, there were some pretty lovable ones and some pretty terrible ones. It's probably pretty hard to keep track of them all, but some could be considered more flings or one-night stands rather than girlfriends. Charlie's girlfriends are much easier to keep track of.

10 Courtney Leopold

This con-artist, bombshell of a girlfriend was a recurring character that appeared in a total of eight episodes. She was one of the best characters to be introduced after season one, as viewers first meet Courtney in Season five as Evelyn's boyfriend's (Teddy) daughter. She manipulated Charlie and they end up "dating," however it's clear she's in it for his money.

Courtney and Teddy were eventually revealed to be con-artists who only wanted Evelyn and Charlie's money. Although Courtney was hilarious, fiery, and definitely a strong woman, the whole criminal thing definitely earns her the bottom spot on this list.

9 Angie

In the fifth season, Charlie actually dated a mature and sophisticated woman for once. Angie was an author, and Charlie actually goes to great lengths to try and make it work with her. However, in an awkward turn of events, it turns out that Angie's daughter-in-law dated (and is still in love with Charlie).

There was some growth from Charlie when he turns the young blonde down to keep dating Angie, but the whole thing still blows up in his face, as the two eventually went their separate ways. Angie was a motherly figure, and she wasn't exactly the most exciting character on this list, hence her earning this not-so-impressive slot.

8 Kandi

Most will probably remember Kandi as Alan's recurring flame, but she did date Charlie first. She first appears in Season three and has a fling with Charlie. They end up breaking up because Charlie meets Mia, who he becomes infatuated with.

While Kandi isn't exactly the sharpest tool in the shed, her humor, free spirit, and total confidence in herself made her lovable. However, she lands relatively low on the list because she isn't super capable of maintaining an interesting personality. She clearly was popular though, as her actor April Bowlby is one of the most followed actors on Instagram to appear in the series.

7 Lydia

In Season 4, Lydia was the girlfriend who pushed Charlie's issues with his mother to the forefront. Lydia worked in real estate and was bossy and manipulative. She had two sons who were much like Charlie and Alan, who Charlie actually did try to get along with.

Their relationship wasn't totally toxic, and Lydia's fiery personality was actually kind of amazing. However, this relationship was weird from the beginning and became even more so when she and Evelyn end up in the same room, as Lydia clearly had animosity towards her.

6 Rose

Fans do not have to be reminded about the whole on-and-off crazy circus that is Rose and Charlie's relationship. Rose appeared in every season and is the only girlfriend of Charlie's to do so. They "dated" a couple of times throughout the series, even getting engaged. Rose was also one of the only women Charlie has ever been with to actually be wealthier than him.

While she appeared wholesome and sweet, Rose was actually a pretty toxic human being. She was funny and kind, but her manipulation behind that veil of sincerity was extremely appalling. However, she made it this far into the list because she was entertaining and a huge part of the series.

5 Sherri

Sherri was almost the female equivalent of Charlie. She played hard to get and was incredibly talented at manipulating Charlie into sleeping with her. However, this doesn't exactly fly with Charlie, because he likes to be the user and not the other way around.

Sherri appeared in three episodes, and it was nice to see her ability to give Charlie a taste of his own medicine. He quickly learned not to mess with this strong woman, a lesson he, unfortunately, did not take with him in later episodes.

4 Linda Harris

Linda met Charlie on a double date, and for once, he began to like a woman that's close to his own age. Linda was a courtroom judge, and her intelligence and reputation were pretty intimidating for Charlie. She was a short-lived character and only lasted a few episodes, although she certainly was a lover who deserved more.

Charlie even babysat her young son, which was a totally unexpected moment of growth for his character. Linda was smart, strong, and probably way too mature for Charlie. She would have been a great long-term girlfriend, but it is easy to admit that she was a bit too serious to be dating Charlie.

3 Lisa

Lisa appeared in the first season of the show, played by star actor Denise Richards, Charlie Sheen's real-life ex-wife. It was revealed that Lisa and Charlie dated before she appeared in the show, with Lisa showing up as the latter's old flame.

Charlie tried to win her back, but Lisa turned him down because of his well-documented commitment issues. Although it didn't work out,  Lisa's fire, kindness, and maturity made her memorable compared to some of Charlie's other flings. This old flame was definitely one Charlie shouldn't have put out.

2 Mia

Mia first appeared in Season three, and Charlie became instantly infatuated. In fact, she was one of two women that ended up seriously engaged to Charlie. Later, however, they call it quits before the wedding day. She appeared in four seasons through the middle and latter portion of the show and created grief for Charlie with his other serious girlfriend, Chelsea. Charlie even crashes her wedding at one point, in a moment where fans really hated Charlie.

Mia's humility, spirit, and self-respect all helped change Charlie's bad habits for a time, setting the stage for him to seriously date Chelsea. Speaking of Chelsea...

1 Chelsea Melini

Chelsea first appeared in Season six as the one woman viewers all thought changed Charlie Harper's womanizing for good. These two actually did get engaged, but they couldn't quite hold on. However, Chelsea's strength, ambition, and total ability to not take any of Charlie's nonsense were rare for a partner of his and quite fun to see.

Chelsea changed Charlie for the better, and fans commend her for it. Chelsea will always be the one that got away for Charlie and fans of the sitcom. She totally deserves the top spot as Charlie's best gal.

NEXT: Charlie Harper & 9 More Shamelessly Womanizing Characters on TV

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