The Most Heartbreaking Moments On Friends

Friends is still one of the most popular shows to ever hit television screens. After enjoying 10 successful seasons while it was originally on the air from 1994 to 2004, the now-classic sitcom has new life thanks to the ability to stream our favorite series over and over (and, let's be honest, over and over and over) again whenever our laugh track-loving hearts desire. Over the course of 236 episodes, the show's group of young and attractive New York City residents caused laughter with the silly situations they found themselves in, while also sparking some serious swooning over their sweet romances. However, the beloved series was also responsible for making fans cry due to storylines that were simply heart-wrenching.

It's impossible to deny that loyal viewers were taken on an emotional roller coaster as they followed the fictional yet often relatable lives of the characters that were played by a now mega famous ensemble cast, which also included impressive guest stars like the ageless Paul Rudd and the charming Tom Selleck. But thanks to writing that perfectly captured devastating developments as well as agonizingly moving performances, fans were more than willing to take the sentimental ride.

And that's why you'll want to grab a few tissues and relive — or discover for the first time — these classic scenes which are the most heartbreaking moments on Friends.

The one when Mr. Heckles dies

Fans of Friends will remember Mr. Heckles (Larry Hankin), the eccentric neighbor who lived below Monica Geller (Courteney Cox) and Rachel Green (Jennifer Aniston). Only popping up to complain about noise or to cause trouble, Heckles wasn't the friendliest man. But when he passed away during the third episode of Season 2, and left the contents of his apartment to "the two noisy girls upstairs," they finally get a glimpse at who he really was before becoming a hoarding hermit.

The experience is particularly jarring for Chandler Bing (Matthew Perry) who realizes that his picky ways might mean that he could end up just like Heckles. Prompting a life-changing perspective for Chandler, he's able to say farewell to his old self while saying goodbye to the neighbor. Just try not to be moved as Chandler turns off the apartment lights for the last time and tells the empty room, "Goodbye, Mr. Heckles. We'll try to keep it down." We're not crying, you're crying.

In October 2019, Hankin talked to AV Club about Mr. Heckles and revealed why the character was killed off. It turns out that Heckles' apartment was needed for another storyline which meant that the writers had to come up with a reason for the character to vacate the space. They asked themselves, "Well, what do we do with Mr. Heckles?" Solution: "Let's give him a heart attack." Even fictional New York real estate is vicious.

The one with the 'agonizing' prom video

Throughout the series' run, Ross Gellar (David Schwimmer) had a serious crush on Rachel and we got a look at his early adoration for her during the 14th episode of Season 2 thanks to a video from Rachel and Monica's high school prom night

When the group of friends watches it together as adults, they see that Ross had quickly gotten dressed up, and was about to step in as Rachel's date when the guy who was supposed to take her failed to show up. However, just as Ross was about to surprise Rachel and be her "knight in shining armor," she runs out the door with the original date who has finally arrived. Ross was left standing in his suit, holding flowers, looking heartbroken. It was a super sad moment to watch — thankfully, it ended with Ross and Rachel getting together because he's her lobster or the person Rachel is meant to be with for life.

In 2016, BuzzFeed deemed it "the best Friends episode ever," blatantly stating that it's "a manipulative b*stard" that "knows how to get to you." Describing the moment when Ross sees that Rachel's date has shown up as an "agonizing sequence," they explain that "at this point it's kind of hard to cope. There are too many feelings, and they are beautiful and painful at once." So true and ouch.

The one when Monica and Richard break up

Monica Gellar's relationship with Richard Burke (Tom Selleck) may have been iffy from the start — you know, since he was her dad's best friend and watched her grow up — but they really were "full of true love and unbridled chemistry," as Bustle explained in a defense of the complicated May-December relationship. That's why it was so tough to watch them break up on the dance floor of a wedding during episode 24 of Season 2.

There was no big fight or wrongdoing which led to the sudden decision, but rather, it was simply the realization the characters were at different places in their lives. Monica wanted to have children and Richard, who was already a father and grandfather, didn't want to start all over again. As they slowly danced while knowing they were splitting, fans surely shed a few tears.

And while it was the end of Selleck's initial run on the show (before he eventually returned for occasional stints), he revealed that he was originally only supposed to be on three episodes. However, the actor told AV Club in 2015 that Monica and Richard's relationship was so well-received by fans, he was asked to stay on, something that he would have done for even longer if he'd been given the chance. "It was a joy," he said, adding, "all of those actors were a joy to work with, and I would've done 30 of them if they'd asked me."

The one where Ross ruins everything

One of the most famous break-ups in television history is also one of the most heartbreaking. Putting aside the question of whether Ross and Rachel were on a break, when Ross slept with another woman during Season 3's episode 15 mere hours after putting things on pause with Rachel, it ruined their relationship. If you haven't already started whimpering while watching Ross try to convince Rachel to forgive him while telling her that he can't imagine his life without her, you'll surely be bawling by the time she tells him she'll never see him the same way again and can't be with him.

It was not only one of the most wrenching moments of the entire series, but it was also a deviation for the original story line. Executive producer and director Kevin S. Bright told Metro in 2018, "I would say initially when [Ross and Rachel's relationship] was planned it wasn't planned that way, that came a little bit later. It allowed us to have fun with the show and give people something to root for."

Bright confessed that the people behind the scenes "were well aware the audience wanted to keep [Ross and Rachel] together," however, they felt like they needed to draw things out so that they could regain the "sexual tension." He explained, "As soon as everyone got their wish the wish was taken away. It made it so much better when they did get together."

The one with Phoebe's cat-mom

While five out of the six main characters on Friends came from stable (even relatively privileged) backgrounds, Phoebe Buffay (Lisa Kudrow) had a childhood that was so "traumatic" that Refinery 29 deemed it "Friends' darkest plotline." The outlet explains, "There's an episode of the sitcom Friends during which Rachel asks Phoebe: 'How have you never been on Oprah?' The question is posed as a joke, but it's not far off base, considering Phoebe Buffay's life was riddled with intense trauma. Although her disturbing life experiences were usually the butt of a joke seemingly added to the script for shock value, it doesn't make them any less harrowing."

That's why it was so silly yet moving when, during the second episode of Season 4, a cat shows up which Phoebe feels is the reincarnated spirit of her mother — who died by suicide. Ross, a skeptical scientist, can't accept the idea and makes sure to tell Phoebe his opinion in a rather harsh, no-nonsense way. She responds by asking him how many parents he's lost and he has to admit that he hasn't lost either of his parents. While she points out that he wouldn't know what it feels like when one comes back, she adds, "I believe this is my mother. Even if I'm wrong, who cares? Just be a friend, okay? Be supportive." He apologizes, but fans were already left sobbing.

The one when Phoebe gives away the triplets

When Phoebe decided to carry a baby (which ended up being three babies) for her brother and sister-in-law, she knew it would be difficult to give the babies up. Her biological mom who had recently come back into her life even presented her with an experiment (involving a puppy) to show her how hard it would be to part with something you love. However, Phoebe went through with the pregnancy anyway, and after giving birth, had to give up the newborns (during the series' 100th episode). "Everyone said labor would be the hardest thing I'd ever have to do but they were wrong," she tells the little ones in her arms. "This is."

What made the scene even more emotional was the fact that Lisa Kudrow was expecting her own baby at the time. While speaking with People magazine in 2018 for their "Celeb Parents Get Real" segment, the actress recalled being pregnant on set, saying, "The six of us [actors on the show] would do a huddle backstage and just say, 'All right, have a good show, love you love you love you love you.' And when I was pregnant, then they would say, 'Have a great show, love you love you — love you, little Julian!' 'Cause we knew it was a boy and that was his name. So sweet, they included my little fetus in the huddle." So sweet, indeed.

The one with Joey's unrequited love for Rachel

While plenty of fans spent the series' run rooting for Ross and Rachel's relationship, there was a time that a romance bloomed between Rachel and Joey Tribbiani (Matt LeBlanc). However, when Joey first developed feelings for Rachel (who was pregnant at the time with Ross' baby, which obviously made things a little more complicated than they already were), she was initially totally oblivious. When Joey did admit his feelings for Rachel during episode 16 of Season 8, she had to tell him that she didn't feel the same way which left them both (and audiences at home) in tears. 

While some viewers had issues with the entire Joey-Rachel relationship from start to finish (and the cast reportedly agreed that it was kind of "incestuous"), former People magazine writer Kelsey Miller (who wrote the book I'll Be There for You: The One About Friends) argues that LeBlanc's "performance was so wrenching that it almost distracted from the ickiness of the story itself."

However, some fans did think Joey was better suited for Rachel, as one explained in a now-deleted Twitter thread [via Cosmopolitan] that their romance bloomed from a good friendship, and "when he tells Rachel how he feels and she turns him down, contrast that with 'WE WERE ON A BREAK. He never blames her and he doesn't let it impact the rest of the group. The friendship stays intact. ROSS GELLER WHAT'S GOOD." Hard to argue with that.

The one when Phoebe and Mike break up

Paul Rudd may play Ant-Man as part of the Marvel Cinematic Universe these days, but years ago, he appeared on Friends as Phoebe's love interest, Mike Hannigan. An irresistibly adorable pair, fans were shocked when the relationship hit a bump in the road just as the two were moving in with each other during the 16th episode of Season 9. Despite being deeply in love, they split in a break-up that no one saw coming after realizing that only one of them saw marriage in their future.

While their separation was temporary, it might have been permanent if Phoebe had ended up with Hank Azaria's character David, as originally intended. "The plan always was kind of to bring him back," Azaria told the Huffington Post in 2016 while talking about his scientist character who left Phoebe (and the country) to pursue his research. "I think, honestly, what happened was Paul Rudd is so awesome that they sort of found a groove with him and [Mike] became more of just the grist for that mill as opposed to the other way around."

"It actually did sting a little bit," Azaria admitted. "Whatever part of me is David the science guy who went to Minsk, which admittedly is probably a small part of me [laughs], but that part of me wanted to end up with Phoebe. So I was sort of sad when I didn't." As if the story line wasn't sad enough!

The one with Monica and Chandler's fertility struggles

Deciding to have a baby can be a joyous time in a person's life. However, it can also become an emotionally trying and downright devastating experience if you have trouble conceiving. That's what Monica and Chandler face during episode 21 of Season 9. After getting fertility tests done, the pair find out that they're unlikely to get pregnant in a scene that's painfully familiar to many who have been through something similar, and nearly as sad to just about everyone else who can sympathize.

When Chandler receives the news via a phone call from the doctor, he must then tell Monica, explaining the situation by saying, "It means that we can keep trying, but there's a good chance this may never happen for us." Watching their dreams of parenthood potentially crushed as they apologize to each other and embrace is simply heart-wrenching. 

It's even more touching considering Courteney Cox experienced her own fertility struggles and had several miscarriages while filming the show. During an interview with NBC News in 2004, while pregnant with her daughter after years of enduring multiple miscarriages, Cox opened up about working on certain baby-related scenes, admitting, "Oh my God, it was terrible having to be funny."

The one when Joey's agent passes away

Saying goodbye to someone who's been part of your life for years isn't easy, especially when that person dies and seems to send you a message from beyond the grave. When Joey's longtime acting agent Estelle Leonard (June Gable) passes away in the 15th episode of the show's final season soon after he fires her, Phoebe tries to protect her friend by keeping him from finding out and feeling guilty about how things had ended with the professional relationship. Although Phoebe first pretends to be Estelle over the phone, she eventually has to end the good-intentioned ruse and calls Joey to offer a final farewell. However, Joey has already learned that Estelle has died and thinks the call is from her ghost.

While it's somewhat funny, it's also sad to watch him say goodbye, especially since fans were likely aware of the fact that this was one of the ways that the show was wrapping up story lines and giving final curtain calls to beloved characters and guest actors that had popped up regularly throughout the years. Gable first played Estelle in 1994 (although her scenes were deleted) before appearing a year later in a totally different role — a nurse who helped deliver Ross' son Ben. In total, she was a part of 11 episodes, not to mention earning a place in television history.

The one with the finale

It's unlikely that anyone expects to watch the final episode of Friends without crying, and the very last scene almost certainly guarantees that anyone who can cry will cry. As Monica and Chandler move out of their apartment to start a new life with their baby twins, the entire group gathers together to leave their keys and close the door for the last time. 

While it's a sad moment for the fictional friends, it was also a brutal scene for fans to watch, and even more difficult for the stars to get through. When they sat down with Oprah not long after filming the finale, Jennifer Aniston explained, "I don't think we've ever taken more time in hair and makeup in between scenes ... we kept crying all our makeup off, over and over again." 

David Schwimmer admitted, "I started to lose it in this ritual that we have before the show which is just a group hug, kind of get in a little circle right before we come out, and that was the moment I was dreading for a long time, because I knew that moment of just looking at everyone in their eyes, and saying, 'Have a good show,' and knowing that was the last time we were going to be able to be in our little circle before the show." Fans may need their own comforting group hug after watching this heartbreaking scene while softly singing, "I'll be there for youuuu."