Two and a Half Men will forever be one of the most popular and hilarious sitcoms out there, and while it has come to an end, fans are still certainly in love with the reruns of this hit series. While Charlie is known as the womanizer, Alan certainly has his fair share of lady friends, too.
Of course, half of the humor of this show is that the dates do not always turn out well. However, he has certainly had a few good eggs that fans fell in love with just as much as he did. Here are 5 of Alan’s girlfriends that we would love to date, and 5 that we definitely would not.
1. Would: Kandi
Kandi is definitely not the sharpest tool in the shed, but she is probably one of the sweetest and most fun women that Alan ever dates throughout the series.
They actually have a pretty serious relationship, and it is probably the only one that fans were behind. Kandi is hilarious and totally free-spirited. While she may not be the best conversationalist, we could all do worse.
2. Wouldn’t: Melissa
Melissa is probably Alan’s most serious and longest-lasting girlfriend on the show. While she seems quirky and cute, the more she appears, the more it becomes clear that she is hateful and, frankly, pretty rude.
It does not end well with Alan, and this is a woman of whom we definitely do not want to get on her bad side. Sure, Alan deserved a lot of it, but her spite and controlling attitude are a bit too much to handle.
3. Would: Frankie
This character appears in the first season. While Frankie (Jenna Elfman) seems a bit unhinged after destroying her ex’s car with a baseball bat, it becomes clear that she has a troubled past and a lot of built-up anger. However, Frankie is also totally fun, and the mother of a young girl, so she is not entirely irresponsible.
While she is not the most stable woman that Alan dates, she actually seemed to be quite an interesting and lovable character. Unfortunately, she moves away to restart her life, leaving Alan in the dust.
4. Wouldn’t: Rose
Rose, brilliantly played by Melanie Lynskey, is a recurring character through all the seasons, and whether she is sticking her claws in Charlie, Walden, or Alan, it is safe to say this woman is dangerous and totally unhinged.
She has a lot of baggage, but Rose is also super manipulative and totally does not understand boundaries. As far as girlfriends are concerned, this is a no-no for any and all fans or potential suitors.
5. Would: Gretchen Martin
Gretchen (Kimberly Williams-Paisley) and Alan date on the pretense that Alan is a totally different person: Jeff Strongman. While this obviously blows up in his face, it is kind of a shame that it did =because this is one of his best girlfriends.
She is quirky and free-spirited, like other women on this list. While not perfect, Gretchen was certainly better than Alan deserved, and would be an interesting woman to get to know in real life.
6. Wouldn’t: Jamie Eckleberry
While this character did not officially date Alan, they were super close in high school, and Jamie had a crush on him. Jamie, played by Paget Brewster, is stunning and confident. However, it is clear that she had a tough time in high school.
As a result, she is fueled by revenge and hatred, and her fuse blows up by the end of her meeting with the Harper brothers. All things considered, this woman might just have a bit too much baggage to handle, as of the time of her appearance on the show.
7. Would: Lyndsey McElroy
Lyndsey (Courtney Thorne-Smith) is a pretty hit-and-miss character. However, she is definitely one of the best women that Alan can say he dated in a long-term relationship.
Lyndsey is smart, funny, and totally independent. While she certainly has her flaws, she is still a pretty great girlfriend. Alan and she were not the greatest as a couple, but that does not mean she would not be a good partner.
8. Wouldn’t: Naomi
Naomi is Berta’s pregnant granddaughter. While Berta thinks that Alan is great for his daughter, that is actually probably the first red flag. Naomi is sweet and honest, but it turns out she also has a thing for weird and low-life men.
After leaving Alan, fans can agree that this woman is a bit unstable and maybe not the brightest of all of the women Alan has dated. She is not the worst, but it probably would still be a pass.
9. Would: Walden Schmidt
Alan and Walden do not actually date throughout the series and Walden is technically not a girlfriend, but they do get married and adopt a son. Besides, the bottom line is that Walden is the best Alan could ever do.
Out of all the women Alan dates, he would have been better off with Walden from day one. This pair is hilarious, and at the end of the day, totally supportive of one another. We would all be happy to date Walden Schmidt, or of course, the real Ashton Kutcher.
10. Wouldn’t: Judith Harper-Melnick
If there is one thing that every fan of this show can agree on, it is that Judith is the epitome of a terrible ex-wife. While we do not know what they were like together, it is probably safe to say that she was selfish and controlling.
She strips Alan dry of money and dignity at any chance she gets, and someone that hateful is certainly not someone we would want to date, and we certainly would not want to have as an ex.
