Two And A Half Men: 5 Of Charlie’s Girlfriends We’d Love To Date (& 5 We Wouldn’t)

It’s been a while since Two and a Half Men had its final season – way back in 2015, but fans of the show still love watching reruns of this hilarious sitcom. Charlie Harper was certainly one of the biggest womanizing characters on television, and pretty much every episode featured one of his flames.

While not every relationship with great, some of these gals were actually way too good for Charlie. To reminisce all the ladies on this show – here are 5 of Charlie’s girlfriends we’d totally date, and 5 we definitely would not.

10 Would Not: Jamie Eckleberry

Jamie was spunky, intelligent, and totally gorgeous, but it turns out that the boys definitely crossed her in the past. Played by Paget Brewster, fans will remember that Charlie used to make fun of her in school before she was “pretty”.

While she seems like a lovely lady, she clearly has some anger issues and some unresolved hatred. It was hilarious to watch, but we’d never want to see that fire directed at ourselves.

9 Would: Lisa

Lisa, played by Charlie Sheen’s IRL ex-wife, Denise Richards, was certainly the flame that got away. She only appears in the first season, but she still remains one of the most down-to-earth, intelligent, and fiery women that Charlie ever dated.

This woman is gorgeous, doesn’t take Charlie’s shenanigans, and has certainly proven she has a heart of gold and a big brain to match. We’ll never forget Lisa, and we’d definitely date this sassy, funny, and intelligent bombshell.

8 Would Not: Courtney Leopold

Courtney was definitely an entertaining character to watch, and Jenny McCarthy absolutely slew her role as this manipulative and fiery woman. Of course, we’re just glad that she was playing Charlie and not us.

She’s certainly intelligent, and she’s actually super funny, but this woman is as dangerous as they come, and we would probably be better off to stay away from her. However, we’ll definitely give her props, and we’re praying for any man she comes across.

7 Would: Myra Melnick

We’ll never forget when Charlie, again, steps out of bounds and begins to date Myra – Judith’s new husband’s sister. While that’s a bit weird, fans absolutely loved this spunky and sassy character, played by the infamous Judy Greer.

Sure, she was actually engaged, and was using Charlie as a final fling, but outside of that, this character seems like a lot of fun. Plus, she’s definitely one of the most intelligent women that Charlie was ever involved with.

6 Would Not: Laura Lang

This bombshell (Heather Locklear) was definitely intelligent. This divorce attorney had a good head on her shoulders, and it’s certainly a shame that she used to manipulate others and get her way. Fans will remember she was actually Alan’s attorney in his divorce, but Charlie, obviously, started dating her.

After things went sideways, Laura showed a pretty petty and vengeful side of herself and ended up giving Judith everything of Alan’s. This kind of spite and hatred is definitely not something we want in a partner, and we’re also not sure we’d want her as a divorce attorney, either.

5 Would: Kate McLaughlin

Kate only appeared in one episode, but she still remains one of the most down-to-earth and relatable women that Charlie dates throughout the series. A single mother who meets Charlie at a soccer game, this woman is honest, caring, and taking life one day at a time.

This hardworking and intelligent character would definitely make for a loyal and sweet girlfriend that anyone would be lucky to have. Plus, Liz Vassey certainly brought this character to life perfectly.

4 Would Not: Rose

Let’s be honest – fans love to hate Rose, who is brilliantly played by Melanie Lynskey. Charlie could never quite kick this woman to the curb. It definitely gets pretty sticky, and it never really gets better.

Rose has a big heart, but the show seriously never should’ve entertained someone as dangerous and wild as this character for so long. She definitely crossed boundaries and did some things that we would rather stay away from. At the end of the day, we’d be a little afraid to date her.

3 Would: Linda Harris

Linda is another character that’s quite frankly just too good for Charlie. While she does care a bit too much about her image, this woman has a job to do, and her hardworking and determined attitude says wonders about her character.

She’s definitely the most intelligent of the bunch, and this judge also proves that she’s pretty fiery and spunky. Plus, she’s a strong single mother. If we were looking for a serious relationship, we’d definitely call Linda.

2 Would Not: Mia Adams

Before there was Chelsea, there was Mia (played by Emmanuelle Vaugier). She was pretty much the only other long-time girlfriend in the show. To be quite honest, fans were pretty annoyed with this woman, and we were all actually kind of grateful when she left.

She was controlling, sassy, and pretty selfish. She changed Charlie way too hard way too fast, and by the end of it, she was in her own little world, annoying fans everywhere. While she was not the worst woman to have been dated by Charlie, we would rather keep her at a distance.

1 Would: Chelsea Melini

Chelsea (Jennifer Taylor) was definitely the best girlfriend of Charlie’s, and was quite honestly always too good for him. She first appeared in season 6, and ended up actually getting engaged to Charlie. While it didn’t work out in the end, Chelsea proved it was because she deserved better.

This smart, ambitious, and beautiful woman did quite a good job pulling Charlie out of bad habits, and we would all love a supportive and intelligent woman like Chelsea at our side.

About The Author

Meah Peers
(631 Articles Published)

I just graduated university with Criminology & Psychology, but have a burning side passion for film! I am an avid reader, writer, and film-goer, and I love learning about movies, actors, directors, and sharing my passion and knowledge with others.
I am a List Writer for ScreenRant, and love being a part of a film community where we all share the same passions.

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