Chandler is easily one of the most beloved characters from Friends and it's safe to say that he's been through his fair share of relationships throughout the 10 seasons of the show. Of course, his dating life came to an abrupt halt after he and Monica got together at the end of season four.
Chandler and Monica's relationship seemed meant to be but it was by no means perfect. Throughout the series, Chandler has come in contact with several women that just might have been a better match for him than Monica. Keep reading to find out the 10 other characters that Chandler should have been with.
Phoebe
Phoebe and Chandler would have made a great couple and it's a shame that the series never gave fans a glimpse at what that would truly look like. In season five, Friends teased a potential relationship between the two but it was all for show. Phoebe was only pretending to be interested in Chandler to get him to crack and reveal his secret relationship with Monica.
This definitely leaves fans to wonder if there could have been something real between Phoebe and Chandler had he and Monica never gotten together.
Rachel
Another good match for Chandler could have been Rachel. Every fan of the series knows that Ross and Rachel were an inevitable couple from the beginning, but what if they weren't? Chandler has a lot of the same qualities that Ross has, not to mention the fact that he treats women exponentially better.
In "The One With The Flashbacks" viewers see that Chandler has previously shown interest in Rachel and these feelings seemed relatively reciprocated on Rachel's end. It would have been great to see these two give a romantic relationship a shot.
Julie
One thing is for sure, Julie got the short end of the stick when it came to finding love with Ross. Ross never gave their relationship a fair shot as he cut it short when he had the opportunity to be with Rachel. Julie definitely deserved better and there's reason to believe she could have found happiness with Chandler.
These two have plenty in common. Both Chandler and Julie love to laugh and joke around. Chandler might not love dogs, but we could definitely see him following through and getting a cat with Julie.
Emily
Emily is another one of Ross's ex-girlfriends that probably should have been with Chandler instead. While many viewers of the series aren't exactly fans of Emily, she still deserved better than Ross. Between saying Rachel's name at the altar and offering to take Rachel on their honeymoon, Ross put Emily in too many sticky situations.
While Chandler has his flaws, such as a lack of communication skills and fear of commitment, he's also one of the most caring and kind-hearted characters on the show. Both he and Emily love their partners deeply, and together they could have gone the distance.
Joanna
Ah, Joanna. While she was a somewhat abrasive character, she and Chandler and had decent chemistry together. Chandler thought Joanna was dull and he didn't like the "mascara goop thing" that she would get in her eye but he continued to see her nonetheless. This was chalked this up to a fear of being honest but it's also possible that he had some feelings for Joanna that he wanted to see through.
Their relationship ended abruptly - and Joanna was later killed off the show - but there's a chance that they could have been great together once Chandler got past his reservations.
Charlie
This may seem like an unlikely pairing, considering Charlie's soft spot for brainiacs, but these two could have definitely hit it off given the chance. Chandler may not be a Nobel Prize winner, but he can certainly hold his own intellectually. Not to mention, Charlie loves a guy who can make her laugh and there's no doubt that Chandler has plenty of jokes.
Things didn't work out for Ross and Charlie but it's possible these two were just too similar. Who knows? Maybe the rule that opposites attract would have proven true for Charlie and Chandler.
Caitlin
There's no denying that these two have chemistry. While Friends fans didn't get to know Caitlin very well, considering she was only in one episode, viewers still witnessed plenty of interactions between her and Chandler. Ross even accused Chandler of flirting with Caitlin since Chandler was dating his sister at the time.
Of course, Chandler denied these accusations but this still left fans wondering if there could have been something between the two of them. Chandler is typically bad with women but for some reason, he was able to flirt with Caitlin effortlessly.
Kathy
When Chandler and Kathy first met in season four, it really seemed like these two were meant to be. There was the minor detail of Joey dating Kathy first, but fans were definitely rooting for Chandler to be with Kathy in the end. Unfortunately, Kathy ended up cheating on Chandler and really hurting him, but only after he accused her of cheating and let his emotions get the best of him.
Both of these characters made their fair share of mistakes in the relationship so it would have been great to eventually see them give things another shot.
Mona
Mona isn't exactly a fan-favorite character, but she could have been had she not been paired with Ross. Mona and Ross's relationship started off strong but things went downhill once Ross found out that Rachel was pregnant. Ross handled the entire situation pretty poorly which forced Mona to ultimately break up with him.
Mona's character had plenty of potential and it would have been interesting to see her paired with Chandler instead of Ross. She didn't join the series until after Chandler and Monica tied the knot, but things might have been different for Chandler had Mona been introduced sooner.
Elizabeth
This character may have gotten a lot of flack for being immature, but she was only a college student so who could blame her? When Ross and Elizabeth got together in season six, their relationship was pretty controversial considering Elizabeth was Ross's student. This relationship eventually came to an end due to Elizabeth's lack of maturity.
Regardless, she could have been a great match for Chandler. Their relationship would have been way less controversial and her maturity level may have better matched Chandler's.