Friends: The 10 Most Painful Break-Ups, Ranked

This iconic series explores the relationships between Rachel, Ross, Chandler, Monica, Phoebe, and Joey. It also explores the heartbreak they face.

Throughout the course of Friends, there is plenty of ups and downs with lots of love and heartache all taking place, showing the reality of life itself with the beloved characters going through the emotional rollercoaster.

During the show, each character has plenty of relationships, with some lasting longer than others and eventually a few even sticking around for the long term. While the people each character ends up with are what most want, that doesn't mean that there aren't great relationships before then.

There are many moments during Friends where it seems like the main characters have found love, only for them to end up breaking up, and some of them are painful to see.

RELATED: Friends: 10 Of Ross Geller's Funniest Meltdowns 

10 Monica & Pete

We kick start this list with one of Monica's relationships. Her break-up with a millionaire named Pete was one that took many people by surprise as the pair seemed incredibly close and were almost set to be engaged at one point.

However, Pete's decision to start a career in MMA ended up being the final straw (for some reason) to this relationship, with Monica seeing him get beat to a pulp in his debut fight, deciding she can't continue with that. Despite that being his dream, it isn't something Monica can support and she ends up dumping him as he goes off to the hospital, which was certainly an emotional break up as she had major feelings for him.

9 Rachel & Joey

This is a controversial example as some people were very glad that Rachel and Joey broke up, whereas others were disappointed about the situation, considering some people were very much hoping that Rachel and Joey would end up together.

Throughout the vast majority of the show, the focus for Rachel in terms of romance is with Ross and the problems that get in their way. But when Friends teased the idea of Joey and Rachel being an item, eventually becoming a couple, it seemed like the Ross and Rachel situation was finally over.

RELATED: Friends: Joey's Girlfriends, Ranked 

Obviously, it wasn't meant to be as Rachel and Ross are each other's lobsters, as we all know. But that didn't mean some fans weren't upset about her and Joey not working out.

8 Joey & Kathy

Speaking of Joey, while the vast majority of his relationships are over and done with incredibly quickly due to the nature of his character, Kathy was someone who he did fall for and it seemed like the pair were quite well suited.

However, the manner of their break-up was extremely emotional, with Kathy breaking Joey's heart and calling things off..because she was in love with Chandler. This was a major moment in the show as it seemed for a while like it was going to cause a major shift.

Thankfully, the friendship was able to sustain this moment, but the break-up and aftermath were certainly one of the tensest moments in their friendship.

7 Rachel & Joshua

Rachel and Joshua were a relationship that really could have worked under different circumstances, and most people felt that Joshua was a good fit for her as he was clearly head over heels for the Rachel, but sadly she didn't offer the same level of commitment.

During this time, Rachel was obsessed with Ross still, and she simply couldn't see past his relationship with Emily, which meant that she and Joshua were doomed from the start, no matter how nice he was.

Joshua was freshly divorced when their relationship started, and he was clearly ready to love again, and people actually ended up feeling sorry for him, rather than Rachel.

6 Ross & Emily

Speaking of Ross and Emily...This was an absolute whirlwind of a relationship that hit 100 mph straight away with the couple falling head over heels for one another and quickly ended up getting married, despite the massive distance between them.

RELATED: Friends: 10 Times Ross Broke Out Hearts

Of course, things become very awkward when Ross actually says Rachel's name during the wedding, which is the moment when you know that it is over, and even though the pair stuck together a little while longer, it was an obvious split.

However, Emily was a character who got a lot of time devoted to her and the two did get along perfectly until Rachel decided to try and intervene.

5 Joey & Janine

Janine was one of the rare partners that Joey seemed to really connect with, as the pair had a really good connection with Janine seemingly understanding Joey for exactly what he was like, with his foolish and silly ways.

While most of his partners were not able to do that, Janine could and this meant that they should have really had a good chance together, but sadly she did not get along with Chandler or Monica, which proved to be a hurdle too high to climb.

Considering how much they mean to Joey, this was never going to work out in the long run, but that didn't make it any less sad when they had to call it quits.

4 Chandler & Janice

Say what you want about Janice and how annoying her infamous cackle might be, but she and Chandler really did share a deep bond, which is why they were on-again, off-again for large portions of the entire show.

RELATED: Friends: Chandler's Girlfriends, Ranked 

Janice made her rounds throughout the male group, with Ross also spending some time with her, but it really is Chandler where she makes her presence known, and at times it did seem like the pair really did love each other.

While sometimes it was clear it would be a one-off, other times, people weren't so sure and that meant that the break-ups were painful and Janice ended up becoming quite the fan-favorite.

3 Rachel & Ross

This one was painful to watch, with viewers having gone through the ups and the downs of Ross and Rachel only for them to end up calling things off, which led to the classic "we were on a break" storyline.

No matter what side of the argument you sit on with that one, this was one of the most emotional moments in the history of the show, with fans being truly heartbroken over the fact they were splitting up, for what seemed to be for good at the time.

The only reason it doesn't rank higher is because of how things inevitably work out between the pair, but when you first view this break-up, it is likely to get even the most stone-cold person tearing up.

2 Phoebe & David

Let's be fair, Phoebe and Mike certainly made an amazing couple with his sarcastic nature suiting her far better than anyone she ever dated on the show, hence why they ended up getting married. However, early on in Friends, there was one other man who seemed to just get Phoebe's quirky personality, and that was David, who might just also be the smartest person that anyone from the group has ever dated as well.

RELATED: Friends: The 10 Worst Things Phoebe Has Done, Ranked 

The fact the show brought him back as a late twist in the Phoebe/Mike story proves how popular this couple was and because people actually thought there was a possibility of her leaving Mike for him shows how big of an impact their initial break-up was.

1 Monica & Richard

Before anyone had even thought of the possibility of Monica being with Chandler, many thought her relationship with Richard was going to be the one, with the pair just suiting each other to perfection, arguably better than she did with Chandler.

However, the one thing that stood in their way was the fact Richard didn't want to have children due to his age and that led a very emotional Monica to make the decision of ending things with him, which was a very sad moment on the show.

While they were only actually dating for 10 episodes on the show, they had a real connection and it felt much longer, which is why so many people were sad to see them not overcome this obstacle.

NEXT: Friends: Monica's Boyfriends, Ranked 

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