Two and a Half Men is one of the more popular sitcoms to ever be made, and much of that has to do with the fun dynamic between the Harper men. Whether it be Charlie's debauchery, Alan's mooch tendencies, or Jake's obliviousness, the three played off of each other perfectly from episode one.
Most fans have forgotten quite a bit about Two and a Half Men's first season, as the dynamics of the show changed drastically after it and new characters were introduced that fans begin to grow attached to. They all had their moments, but few stand out for making the show much more enjoyable when they showed up.
10 Teddy Leopold
Evelyn Harper, the matriarch of the Harper family, was known throughout the show for her many relationships, including several ex-husbands. The only one we get to see in the show is Teddy Leopold, who quickly becomes infatuated with her. Teddy asks Charlie and Alan for their blessing to marry Evelyn, and, after a fun night in Las Vegas, the two agree.
On the night of their wedding, Teddy dies inexplicably, and it is revealed that Teddy is actually Nathan Krunk, a professional con artist. His desire not to do a prenup before the wedding was his plan to take all of Evelyn's money—and she was one of Two and a Half Men's wealthiest characters. While it certainly wasn't a happy ending, it was a fun way to see what Evelyn's romances were like.
9 Courtney Leopold
As Teddy and Evelyn prepare for their wedding, Teddy introduces everyone to his daughter Courtney and immediately Charlie falls for her. Courtney uses Charlie to get him to buy her nice things and even gets a loan from him. After the death of Teddy, Courtney is revealed to be Sylvia Fishman, and she was Teddy's partner in their plan to rob Evelyn.
Sylvia would pop up again after getting out of jail, and Charlie was still smitten with her, falling right back into her trap of getting whatever she wanted from him. She was always pulling a con of some sort on Charlie, but he was still attracted to her despite everything she did to him.
8 Eldridge Mackelroy
Jake, for most of the early run of the show, was just Alan's kid who got into a bit of mischief, but only really childish levels of mischief. Once Eldridge, Lyndsey's teenage son, came into the picture, that level of mischief certainly changed.
Eldridge and Jake were best friends, and the dynamic duo was routinely in over their heads with the trouble they got themselves in. Whether it was getting drunk off of Charlie's beer, downloading porn to the servers at Walden's company, or being tricked into joining the military, they were a perfect match when it came to making bad decisions together.
7 Kandi
Kandi started as another fling of Charlie's, but, when it's made clear that Charlie isn't interested in her, she moves on to Alan. Kandi is a bit ditsy but extremely kind, so Alan becomes infatuated with her. The two's relationship progresses rapidly, with Alan paying all of Kandi's expenses and moving into his room.
When the two are in Vegas for what was supposed to be Charlie's wedding, they end up getting married, instead. The marriage is short-lived, as Kandi files for divorce out of the blue and kicks Alan out of their new condo. The two attempt to reconcile, but, when Kandi gets a job on a television show, she kicks Alan out, and they never see each other again.
6 Dr. Linda Freeman
When Judith and Alan got divorced, Judith thought it would be smart to have Jake see a child therapist to make the divorce a little easier for him. That therapist is Dr. Linda Freeman, and she tries her best at getting something out of Jake. Her true breakthroughs come from the older Harper men.
Dr. Freeman becomes the therapist to both Alan and Charlie, helping them try to cope with their issues, both between each other and separately. What makes Dr. Freeman so fun is the sarcastic tone she treats them with, while still assisting them the best she can with their shenanigans.
5 Chelsea
Chelsea has the distinction that many other women in Charlie's life never did, as she was able to get him to commit to their relationship. What started as a one-night stand led to Charlie telling Chelsea that he loves her and eventually proposing and the two moving in together.
Not only was Chelsea one of the most positive women Charlie dated throughout his tenure on Two and a Half Men, but she developed strong relationships with everyone in his life. She was willing to put up with all of Charlie's debauchery because she truly loved him. Although their relationship ended poorly, there is no denying that Chelsea was the best relationship Charlie had in the show.
4 Jenny Harper
Charlie was a part of the driving force that made Two and a Half Men one of the most popular sitcoms ever, and losing that character was certainly a blow to the show. Thankfully, a new version of Charlie was brought in late in the show's run, as his daughter Jenny shows up in Malibu and does a few terrible things of which Charlie would likely have been proud.
Jenny proved to everyone that she is indeed a spitting image of her father, from the excessive drinking to her relations with many different women. Jenny meshes well into the family dynamic and was a nice shot in the arm for fans who missed Charlie.
3 Lyndsey Mackelroy
Alan hasn't had many relationships of note throughout the show's run, but, of them all, his relationship with Lyndsey is the most strongly developed. After meeting in season 7, Lyndsey and Alan had an off-and-on relationship with more bad times than good. It wasn't always as bad as Alan burning her house down, but it still wasn't a great relationship between the two.
Lyndsey is kind of a trainwreck when it comes to relationships, as she tends to cheat on all of her boyfriends, including Alan. Part of the reason the two always kept coming back to each other is that they were very similar people in that they are their own worst enemies.
2 Dr. Herb Melnick
After Alan and Judith got divorced, Judith wasted no time in moving on to her next man, as in walked Dr. Herb Melnick. Herb was Jake's pediatrician, so a relationship of some sort was already established, but it became serious enough that the two eventually got married.
While Alan early on never fully approved of Judith and Herb, he eventually comes around, even with the two becoming friends. Herb develops a fun friendship with Charlie, as well, being envious of his lifestyle. Alan does his best to give Herb advice on how to be married to Judith, but the marriage is far from perfect, with the ups and downs eventually leading to a divorce.
1 Walden Schmidt
After the death of Charlie Harper, it was up in the air what would happen to Alan without his brother to mooch off of. Luckily for him, Walden arrives out of the ocean after trying to drown himself due to his wife throwing him out of the house. Walden and Alan develop a quick bond of friendship, so, when Walden buys the Malibu house, he invites Alan and Jake to stay with him.
Walden was a nice breath of fresh air to the show after the departure of Charlie, as the two couldn't be more different. While he is immature, Walden is quite smart, as he designed a website that was purchased and led to his billions of dollars. Throughout the rest of the show's run, Walden grows up and becomes close to everyone in the cast, even calling Alan his best friend.
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