Ranking the 10 saddest Friends episodes

The Final Days Of "Friends"
The Final Days Of "Friends" / David Hume Kennerly/GettyImages
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Just because a show is filed under the genre "sitcom" does not mean it's all fun times and giggles. All the best sitcoms include a splash of drama, heartbreak, and even mystery. One example of the perfect sitcom that has it all, is Friends.

The viral NBC hit series took fans on a decade-long wild roller coaster of emotions from 1994 to 2004. From debating with fellow fans whether or not Ross and Rachel were on a break, to never knowing if Phoebe's mysterious roommate Denise truly existed, Friends kept viewers on the edge of their seats. But when we weren't laughing or problem-solving, Friends had us in tears!

Friends may be a sitcom, but it never pulled any punches when it came to making us all cry. Ready to sob? Go grab some snacks and a box of tissues, here are 10 of the saddest Friends episodes.

10) Season 2, episode 16, "The One Where Joey Moves Out"

This heartache came at us way too early in the show! The friendship between Joey and Chandler is one of my favorite things about Friends. Think about it, did we not have the most laughs when the duo was on the screen? "The One Where Joey Moves Out" made us wonder if any more friendships (or relationships) in the sitcom will, eventually, come to an end. Fortunately, the best of the best stuck around until the final episode, but we still can't watch "The One Where Jowy Moves Out" without a few tears dropping.

9) Season 3, episode 13, "The One Where Ross and Rachel Take a Break"

Ross and Rachel were very much on-and-off throughout the series, but it still hurt when we saw them break up in season 3, episode 13, "The One Where Ross and Rachel Take a Break." Everything was going well, but Ross' jealousy became too much for Rachel to handle. Not to mention, Rachel felt disrespected each time Ross questioned her.

After an emotional fight, Ross makes the mistake of sleeping with another woman. Meanwhile, Rachel thinks it all over and decides to give their relationship another chance, only to learn that Ross cheated -- or did he even really cheat? It all depends on whether you are Team Break or not. But even if you are Team Break, Ross jumping into a one-night-stand was way too quick.

8) Season 5, episode 14, "The One Where Everybody Finds Out"

Okay, hear me out. This episode made us all cry for sure, but in a good way! "The One Where Everybody Finds Out" solidifies our favorite romantic relationship in Friends, and that's Monica and Chandler. The couple kept their romance a secret, but everyone eventually finds out, but not before they played a daring game of chicken!

Phoebe pretends to be interested in Chandler to get him to crack and confess that he is sleeping with Monica. Little did they all know, that Monica and Chandler were actually in love.

7) Season 2, episode 8, "The One With The List"

Ross, what a jerk you are! Or were, in this episode, at least. While I don't blame Ross for putting together a list of the pros and cons of dating either Julie or Rachel, I do think Ross should have been a lot more careful about keeping the list a secret. That said, asking Chandler and Joey for help with the list was a huge NO. Not to mention, making sure Rachel never got her hands on that piece of paper.

Needless to say, Rachel was heartbroken when she read the list, especially reading the line "She's just a waitress." Ouch.

6) Season 9, episode 21, "The One With the Fertility Test"

Of all the couples in Friends, there's no doubt Monica and Chandler went through it the most. Sorry, Rachel and Ross, but it's true! Monica and Chandler had no time for drama or being on-and-off, their issues were as real as they get! Emma's (Ross and Rachel's baby girl) birth brought everyone so much joy! Chandler and Monica decided they wanted to become parents.

Unfortunately, try as they might, Chandler and Monica could not get pregnant. After countless failed attempts, the couple visits a fertility doctor who reveals that both Chandler and Monica are not able to have kids. We can't help but cry with them when they learn this horrible news -- they were the most deserving couple! Luckily, it all works out in the end.

5) Season 5, episode 3, "The One Hundredth"

Okay, who is cutting onions? I can't even think of this episode without getting emotional. When asked to be her brother's surrogate, Phoebe did not hesitate to accept! And she enjoyed the journey, but it didn't come without heartache.

Shortly after giving birth to the triplets, Phoebe must say goodbye, but she is in denial. While chatting with Rachel, Phoebe tells her that she plans on asking if she can keep one of the babies. After all, there are three, right? Rachel talks to Phoebe, gently explaining to her friend that these babies are more than just numbers to Phoebe's brother and his wife. It's a very sad moment, but I'm glad we got to see the triplets again and we learned that Phoebe has a close relationship with them.

4) Season 10, episode 9, "The One with the Birth Mother"

The episode "The One with the Birth Mother" still has the power to make me cry! Monica and Chandler travel to Ohio to meet Erica (played by Anna Faris), the potential birth mother of their child. They try not to get their hopes up, but this is such an emotional situation, that it's hard not to!

In an attempt to convince Erica to pick him and Monica as the parents, Chandler gives one of the best and most heartfelt speeches in the series. Chandler tells Erica that Monica is already an amazing mother, a mother without a child and that it kills him not to be able to give that to Monica. Tears. Tears all around.

3) Season 6, episode 24 and episode 25, "The One with the Proposal"

Let me start by saying that I love this episode because I couldn't WAIT for Ross and Elizabeth to break up. It's funny that it took a water balloon fight for this to happen. But that's not why this episode is sad, it's the sweet proposal between Monica and Chandler.

Chandler was ready to pop the question, but Monica's ex-boyfriend Richard walked into the restaurant, ruining the moment. To throw Monica off his scent, Chandler pretends not to care about marriage. This confuses Monica, especially when Richard declares his love for her. Wanting to clear things up with Monica, Chandler goes back to Monica's apartment, only to find Monica already there, waiting to propose.

2) Season 10, episode 17 and episode 18, "The Last One"

You'll see this episode on the list twice because it just features one too many sad moments. We are saving the big finale for the end, but before we get to that heartbreaking goodbye, Friend had us shouting at our screen demanding to know if Rachel got off the plane or not. Don't you love love?!

1) Season 10, episode 17 and episode 18, "The Last One"

Was there ever any doubt that this would be the saddest episode from Friends? We were not ready to say goodbye, but it was time to move on. But what made things even more depressing, was to see how sad the cast was, as well. And was it necessary to show audiences the empty apartment? Ugh. My heart!

I don't know about you, but if I see Friends playing on TV, I always leave it on. It's a show I watch frequently! All episodes are streaming on Max, including Friends: The Reunion. Now go grab those tissues and rewatch these sad episodes!

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