Sitcom fans are all familiar with the infamous Charlie Harper on the striking comedyIi and a Half Men. He was ane of the show's principal characters in the first viii seasons, and throughout these episodes, the womanizer dated enough of women.

Some of them simply lasted a unmarried episode, while others made information technology longer. Of course, in that location were some pretty lovable ones and some pretty terrible ones. Information technology's probably pretty hard to keep rail of them all, only some could be considered more flings or one-nighttime 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 full of eight episodes. She was one of the all-time characters to be introduced after flavor ane, as viewers first meet Courtney in Season five as Evelyn'south boyfriend's (Teddy) daughter. She manipulated Charlie and they finish up "dating," however it's clear she'southward in it for his coin.

Courtney and Teddy were somewhen revealed to exist con-artists who only wanted Evelyn and Charlie's money. Although Courtney was hilarious, peppery, 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 really dated a mature and sophisticated woman for in one case. Angie was an author, and Charlie actually goes to great lengths to try and make information technology work with her. However, in an awkward plow of events, information technology turns out that Angie's girl-in-law dated (and is withal in beloved with Charlie).

There was some growth from Charlie when he turns the young blonde downwards to go along dating Angie, just the whole thing nonetheless blows upwardly in his face, as the two eventually went their separate ways. Angie was a motherly figure, and she wasn't exactly the most heady character on this listing, hence her earning this not-so-impressive slot.

eight Kandi

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

While Kandi isn't exactly the sharpest tool in the shed, her humor, gratis spirit, and total confidence in herself fabricated 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, every bit her thespian Apr Bowlby is one of the most followed actors on Instagram to appear in the series.

vii Lydia

In Flavor iv, Lydia was the girlfriend who pushed Charlie's issues with his female parent to the forefront. Lydia worked in real manor and was bossy and manipulative. She had 2 sons who were much similar Charlie and Alan, who Charlie actually did try to get forth with.

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

6 Rose

Fans exercise not have to exist reminded near 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'southward to do then. They "dated" a couple of times throughout the series, even getting engaged. Rose was besides 1 of the only women Charlie has e'er been with to actually be wealthier than him.

While she appeared wholesome and sweet, Rose was actually a pretty toxic homo beingness. She was funny and kind, just her manipulation backside that veil of sincerity was extremely appalling. Even so, she made it this far into the list considering she was entertaining and a huge part of the series.

v Sherri

Sherri was well-nigh the female equivalent of Charlie. She played hard to get and was incredibly talented at manipulating Charlie into sleeping with her. Nevertheless, this doesn't exactly fly with Charlie, because he likes to be the user and not the other mode effectually.

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

4 Linda Harris

Linda met Charlie on a double date, and for one time, 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 just 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 grapheme. Linda was smart, potent, and probably way too mature for Charlie. She would accept been a great long-term girlfriend, but it is easy to acknowledge that she was a bit too serious to be dating Charlie.

iii Lisa

Lisa appeared in the first season of the show, played by star actor Denise Richards, Charlie Sheen's real-life ex-wife. Information technology was revealed that Lisa and Charlie dated before she appeared in the bear witness, with Lisa showing upwards every bit the latter's old flame.

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

2 Mia

Mia first appeared in Season three, and Charlie became instantly infatuated. In fact, she was ane of two women that ended up seriously engaged to Charlie. Later, however, they telephone call it quits before the wedding day. She appeared in 4 seasons through the middle and latter portion of the prove and created grief for Charlie with his other serious girlfriend, Chelsea. Charlie even crashes her wedding ceremony at one point, in a moment where fans really hated Charlie.

Mia'south humility, spirit, and self-respect all helped modify Charlie'south bad habits for a fourth dimension, setting the stage for him to seriously appointment Chelsea. Speaking of Chelsea...

i Chelsea Melini

Chelsea first appeared in Season vi as the ane woman viewers all thought changed Charlie Harper's womanizing for good. These ii actually did get engaged, but they couldn't quite hold on. However, Chelsea'southward strength, ambition, and full ability to not take any of Charlie'south nonsense were rare for a partner of his and quite fun to come across.

Chelsea changed Charlie for the amend, and fans commend her for information technology. Chelsea will always be the ane that got abroad for Charlie and fans of the sitcom. She totally deserves the top spot every bit Charlie'south best gal.

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

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About The Writer

Meah Peers (631 Articles Published)

I just graduated university with Criminology & Psychology, but take a called-for side passion for movie! I am an avid reader, writer, and flick-goer, and I dear learning about movies, actors, directors, and sharing my passion and noesis with others. I am a List Writer for ScreenRant, and love being a office of a flick customs where we all share the same passions.

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