Summary

• Ross had a variety of girlfriends throughout the show, but not all of them were compatible with him. Jill and Elizabeth were the least fitting matches for him, with manipulative motives and a problematic power dynamic.
• Ross also had some relationships that had potential but ultimately didn't work out. Chloe, Bonnie, and Charlie could have been good matches, but timing and other circumstances got in the way.
• Despite his other relationships, it was clear from the beginning that Ross and Rachel were meant to be. They complemented each other well, had a deep history, and could discuss almost anything, making them the ultimate compatible couple in Friends.

Ross Geller is best known as one half of Friends’ most iconic couple, but Rachel wasn't the only girlfriend Ross had on the show. Over 10 seasons, Ross dated a total of twelve women, and he even married three of them. Ross might have considered himself supremely unlucky in love during the show's run, but he tried to find someone he was compatible with over those ten seasons. Some of the women he dated, even if the relationships were short-lived, were great matches for him.

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As is the case with many sitcoms of the era, romance and intimate relationships are a huge part of Friends. Every major character had multiple romantic flings, both short and long-term, but Ross' dating life was arguably the most interesting. Something of a loveable goofball, Ross' many trials and tribulations in the world of romance were a major part of what made the show so relatable and rewatchable. From a woman who only wanted to manipulate him to his true love, these are all of Ross' girlfriends in Friends listed according to compatibility.

Jill (Season 6)

Played by Reese Witherspoon

Jill is definitely the least compatible—and potentially the worst—of Ross' girlfriends. Played by Friends guest star Reese Witherspoon, Jill's motives when it comes to dating Ross are completely self-serving. She didn't actually like Ross, something he was completely unaware of when they met up.

She pretends to be interested in him and share some of his interests because she wants to get back at her big sister Rachel. Ross doesn't know the full extent of Jill's manipulation right away, and it's really unfair to him to be caught in the middle of an argument between sisters. Ross might make some bad decisions in his dating life, but he never intentionally uses someone.

Reese Witherspoon and Jennifer Aniston have worked together since Friends, playing news anchors on the AppleTV+ series The Morning Show.

Elizabeth (Season 6)

Played by Alexandra Holden

Elizabeth was a very sweet girl, but this was an incredibly problematic pairing in Friends. Before she became one of Ross' girlfriends, she was one of Ross’ students when the pair met during the show’s sixth season. They started dating after the semester ended. However, given the wide age gap and the way they met, this pairing never seemed quite right—and, in the end, that caused the relationship’s downfall.

Ross was an adult with a career and a young son. Meanwhile, Elizabeth was still a college student who didn't yet have the same concerns or interests as Ross and his friends. Had Elizabeth been a few years older or not in his class, things might have been different, but, when they met, Elizabeth wasn’t yet mature enough for Ross, and there was a difficult power dynamic, making her one of the most ill-fitting of Ross's girlfriends.

Chloe (Season 3)

Played by Angela Featherstone

Chloe and Ross don't technically date. Rather, they have one night together that drastically changes another relationship in Ross' life. Chloe is the infamous woman from the copy place with the belly button ring that the guys talk about early in the show. She's the person Ross spends the night with while on his "break" from Rachel.

The audience doesn't really get to know her very well, beyond how Ross, Joey, and Chandler talk about her. Other than the two being attracted to one another, it doesn't seem like there's much else between Ross and Chloe. They don't try to really date or get to know each other at all after their one-night stand. The audience will never know if that's the right call or if she had the potential to be a fitting match for him as a result.

Janice (Season 5)

Played by Maggie Wheeler

Throughout Friends, Janice was frequently on-again, off-again with Chandler. But, when she showed up in season 5, it was after hooking up with, and briefly becoming, Ross' girlfriend. Ross was having a hard time after learning his ex-wife Emily was getting remarried, and he actually appreciated Janice’s willingness to lend a sympathetic ear.

Although Ross would have continued to date her, it was Janice who ultimately broke things off. Janice may have been known as a grating, annoying character, among the friend group but Ross’ whining was so incessant that she couldn’t put up with it. The two of them would have annoyed one another too much long term as they both talked about all of one another's faults to anyone who would listen.

Bonnie (Season 3)

Played by Christine Taylor

Bonnie was the first girl Ross dated after he and Rachel broke up in Friends’ third season. Phoebe set the duo up, and, to Ross’ surprise, he really liked Bonnie—and it’s no wonder; Bonnie was a lot of fun. She was outgoing, uninhibited, and very unlike Rachel or any of the other women Ross had dated.

However, it was clear from the beginning the relationship wasn’t built to last. Ross still wasn’t completely over Rachel, so, as soon as the opportunity presented itself, he broke up with Bonnie to get back together—albeit very briefly—with her. He also was incredibly shallow when it came to Bonnie's appearance. He couldn't get ed Bonnie shaving her head after Rachel convinced her to do it.

Cheryl (Season 4)

Played by Rebecca Romijn

Cheryl had a lot going for her. Not only was she exceptionally attractive, but she was also a paleontologist which made her surprisingly compatible with Ross. They could actually talk about their work with one another, something Ross couldn't do with most of his girlfriends. There was just one huge problem; she was messy—and not just typical messy. She was apartment-covered-in-trash-messy.

Ross attempted to get over it because everything else about Cheryl was pretty fantastic. Unfortunately, Cheryl's dirty lifestyle ended up being a deal-breaker, and, since Cheryl seemed unwilling to consider the idea of maybe cleaning up a bit, it was probably for the best. Ross was used to his sister's need for everything to be clean and in its place, so he wouldn't have been able to adjust to Cheryl's chaotic and messy living situation.

Cheryl marked Rebecca Romijn's very first onscreen speaking role. She's gone on to star in television shows like Ugly Betty, The Librarians, and Star Trek: Strange New Worlds.

Charlie (Season 9 -10)

Played by Aisha Tyler

In many ways, Charlie was a great fit for Ross. She was a fellow paleontology professor like Cheryl and his intellectual equal. She even got along with his friends. Yet, she didn’t really seem to know what she wanted in her personal life.

Ross wanted to ask her out when they first met in season 9, but, instead, she started dating Joey. She then dumped Joey for Ross and eventually dumped Ross to get back together with her ex. Charlie was searching for something in a partner that she just didn't seem to be finding. If she was more certain about who she wanted to be with, it’s possible things could have worked out—or, at least, Ross could have avoided getting hurt.

Emily (Season 4 - 5)

Played by Helen Baxendale

Many Friends fans hated Emily, whom Ross met and married in season 4. It was so soon after Ross’ breakup with Rachel that jumping into such a serious relationship so fast seemed like a betrayal of what he had with her. Yet, in fairness to Emily, none of that was her fault. Some Friends fans might have wanted the story cut altogether, but others think it should have played out farther down the line, giving some breathing room between storylines involving Ross' girlfriends.

Emily clearly loved and ed Ross. She even agreed to move to New York to be with him. It’s true that, after Ross said Rachel’s name at their wedding, Emily became controlling. She didn't want Ross to see Rachel again, which was understandable since he said the other woman's name at their wedding, but still went through with the wedding. Her need to know where Ross was and what he was doing became the biggest part of her character, though, as their relationship crumbled. Ross should have been honest about his conflicted feelings with her from the start.

Mona (Season 8)

Played by Bonnie Somerville

Ross met Mona at Monica and Chandler’s wedding and won her affection soon afterward. Unfortunately, their relationship also coincided with Ross learning that Rachel was pregnant with his child. Because of everything that was going on in his life, Ross was constantly forgetting about Mona or failing to tell her the truth about what was going on. He didn't make his relationship with Mona a priority in his life, which was a recipe for disaster.

After Rachel moved into Ross’ apartment and Ross lied to her about it, Mona finally dumped him. It really was a shame, though; of all Ross’ girlfriends, Mona seemed most tolerant of all his quirky habits. Plus, she enjoyed the inane facts he would periodically spout. If the timing had been different, these two might have really had something.

Carol (Season 1)

Played by Jane Sibbett

Carol was Ross’ first wife. When Friends started, they had just broken up because Carol had recently come out as a lesbian. While Carol ended up with Susan, the fact that she was already pregnant with Ross’ baby ensured she stayed a part of his life. The two agreed to parent Ben together, even though they might have had different opinions about how to do just that. Despite the breakup, the two remained friendly, and, through their interactions over the course of the show, it became clear that, at one time, they probably made a decent couple.

In fact, she might even be Ross' best ex in the entire Friends series. The issue with Carol, however, is that the pair probably never should have been a couple in the first place. They would have been better off as friends from the get-go. Carol understood Ross' quirks and was able to deal with them much better than some of Ross' other girlfriends. She also was able to act as a negotiator between her wife and her ex-husband once all three of them were parenting Ben.