Two And A Half Men: Charlie's Girlfriends, Ranked

We're all familiar with the infamous "Charlie Harper" on the hit sitcom Two and a Half Men. The sitcom's main character in the first eight seasons, and throughout these episodes, this womanizer dates A LOT of women.

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Some of them only lasted a single episode, and others made it quite a few. Of course, there were some pretty lovable ones and some pretty terrible ones. We get it, it's probably pretty hard to keep track of them all, so we've done it for you. Here are Charlie's 10 top girlfriends, ranked.

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10 Courtney Leopold

This con-artist/bombshell/girlfriend is a recurring character that appears in a total of 8 episodes. We first meet Courtney in Season 5 as Evelyn's boyfriend's (Teddy) daughter. She manipulates Charlie and they end up "dating," however it's clear she's in it for the money.

In fact, Courtney and Teddy are revealed to be con-artists who actually wanted both Evelyn and Charlie's money. Although we find Courtney 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 dates a mature and sophisticated woman. Angie is an author, and Charlie actually goes to great lengths to try and make it work with this woman. However, it turns out that Angie's daughter dated (and is still in love with Charlie), yikes.

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We see some pretty great growth from Charlie when he turns the young blonde down to keep dating Angie, but the whole thing still blows up in his face. 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

We all probably remember Kandi as Alan's recurring flame, but she did in fact date Charlie first. She first appears in Season 3 and has a fling with Charlie. They actually break up because Charlie meets Mia, who he becomes infatuated with.

While Kandi isn't exactly the brightest tool in the shed, we love her humor, free-spirit, and total confidence. The Harper brothers could definitely do worse. However, she lands relatively low on the list because she isn't super capable of maintaining an interesting personality.

7 Lydia

In Season 4, Lydia is the girlfriend who pushed Charlie's mother issues to the forefront. Lydia works in real estate and is bossy and manipulative. She has two sons (much like Charlie and Alan), to which Charlie actually does try and get along with.

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This 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. Yikes.

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 appears in every season and is the only girlfriend of Charlie's to do so. They "date' a couple of times throughout the series, even getting engaged.

Say what you want about Rose, but she's a pretty toxic human being. Sure, she's funny and kind, but boy she's lost her marbles, and those manipulative claws definitely got the best of Charlie AND Alan. However, she made it this far into the list because, let's be honest, we all kind of love her.

5 Sherri

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

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However, this bombshell appears in three episodes, and we loved her ability to give Charlie a taste of his own medicine. Don't mess with this strong woman.

4 Linda Harris

Linda meets Charlie on a double date, and Charlie for once begins to like a woman that's close to his own age. Linda is a judge, and her intelligence and reputation are pretty intimidating for Charlie.

We even see Charlie babysit her young son, which is a total growth moment for his character. Linda is smart, strong, and honestly, way too good for Charlie. We loved her, but we're going to admit that she was a bit too serious to be dating our man Charlie.

3 Lisa

Lisa appears in the first season of the show (and is actually played by Denise Richards, Charlie Sheen's IRL ex-wife). It's revealed that Lisa and Charlie dated before she appeared in the show, with Lisa showing up as the latter's old flame.

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Charlie tries to win her back but Lisa turns him down because of his commitment issues. Although it didn't work out, we loved Lisa's fire, kindness, and maturity. This old flame was definitely one Charlie shouldn't have put out.

2 Mia

Mia first appears in Season 3, and Charlie becomes instantly infatuated. In fact, she's one of two women that ends up *seriously* engaged to Charlie. Later, however, they call it quits. She appears in Season 5-7, 9, and 12, though, and creates grief for Charlie with his other serious girlfriend, Chelsea.

We loved Mia's humility, spirit, and self-respect that all helped change Charlie's bad habits. However, let's be honest, we all wanted her to get the heck out when Chelsea came into the picture.

1 Chelsea Melini

Chelsea appears in Season 6 and is the one woman we all thought changed Charlie Harper's womanizing for the final time. These two actually do get engaged, but they couldn't quite hold on. However, we still loved Chelsea for her strength, ambition, and total ability to not take any of Charlie's nonsense.

This woman changed this man for the better, and we commend her for it. Chelsea will always be the one that got away for Charlie and fans of the sitcom. You were missed, Chels, and totally deserve the #1 spot as Charlie's best gal.

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