11 Moments On 'Friends' That Broke Your Heart

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Friends will always be a timeless sitcom thanks to the show's many love lessons, its realistic take on friendships, and its jokes and catchphrases that have pretty much influenced an entire generation. But for all of the happy moments on the show that are never to be forgotten about, there are just as many moments in which Friends broke your heart beyond repair. For ten seasons, the iconic group of six experienced some wild times that any friend group could only hope to live up to.

The show was filled with iconic television moments that had the power to repeatedly make you laugh until your sides hurt. Yet for every side-splitting moment the gang endured on the show, there was always another moment or storyline that was nothing short of heartbreaking. Sure, Ross and Rachel were able to find their happy ending when it was all said and done, but watching them break up after taking a break probably still causes you all sorts of emotional distress to this day. Likewise, the relationship saga between Monica and Chandler had its ups and downs as well.

Keep reading below for some of the saddest moments on Friends that probably made you cry actual tears.

1When Ross & Rachel Broke Up

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At first, the couple was just on a break that's now infamous for the way in which it was miscommunicated. But the damage was pretty much done after Ross slept with someone else during their break, causing them to call it quits for real.

2When Ross Said Rachel's Name At His & Emily's Wedding

The fact that Ross mistakenly refers to Emily as Rachel is bad enough, but for something like that to happen as the two are exchanging vows makes this entire situation that much worse and so cringe-y to watch.

3When Phoebe Said Goodbye To The Triplets

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After giving birth to her brother's triplets and making an attempt to keep one, Phoebe has a talk with her surrogate babies and gives them the most heartbreaking goodbye you'll ever hear.

4When Richard & Monica Broke Up At A Wedding

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While at Barry and Mindy's wedding, Richard and Monica have a disagreement about their differing plans for the future: Monica sees a future with children, while Richard sees the couple growing to be happy without kids. Their failure to compromise with each other ultimately leads the couple to end their relationship on the dance floor.

5Monica & Chandler's Proposal

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In an episode that probably made the entire Friends fandom cry, Monica gets down on her knees and attempts to propose to Chandler (who then proposes to instead). Talk about one of the sweetest things you could ever witness.

6When Rachel Got Off The Plane

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Just as Rachel is about to jet off to Paris to start a new job in the series finale, she changes her plan at the last minute, getting off of her plane and returning to Ross so the two can finally have their happy ending.

7When Chandler & Monica Found Out They Couldn't Have Children

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In Season 9, Monica and Chandler receive some test results that reveal that the couple may never be able to have children of their own. Obviously just knowing how badly Monica has wanted children throughout the entire series makes this scene that much more devastating to get through.

8When Joey Admitted His Feelings For Rachel

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Joey confesses his romantic feelings to Rachel, who is pregnant at the time. Rachel lets him know that she doesn't reciprocate his feelings in one of the most touching scenes.

9When Joey & Chandler Miss Each Other After Joey Moves Out

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After having a fight about their living situation, Joey and Chandler decide to go their separate ways. Joey's decision to move out the apartment he shared with Chandler was pretty sad, but at least we were left with this hilarious sequence of both of the former-roommates dramatically staring out the window watching the rain fall.

10When Phoebe & Mike Got Married

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In the final season, Phoebe marries Mike in what could be considered one of the most touching wedding ceremonies on television.

11When The Gang Said Their Final Goodbyes

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Watching the show's final scene will probably never not be hard to watch. Whether you're a huge fan of the show or not, it's hard to hold back tears watching the gang give back the keys to the apartment that held a decade of on-screen memories for them.

Kudos to you if you were able to make it through this with dry eyes.