15 Most Heartbreaking Moments From Friends

It’s like you’re always stuck in second gear. Oh, when it hasn’t been your day, your week, your month, or even your year. I’ll be there for you. Friends is one of the most popular sitcoms of all time. David Crane and Marta Kauffman created the series and it aired for 10 seasons from September 22, 1994 to May 6, 2004. The series revolved around 6 best friends living in New York City as they struggled to deal with their careers, love lives and each other. These 6 best friends made each other laugh and cry. However, often they would break their fans' hearts into millions of pieces with some very sad moments.

Friends aired on NBC and starred a phenomenal ensemble cast. The series starred Jennifer Aniston, Lisa Kudrow, David Schwimmer, Courteney Cox, Matthew Perry and Matt LeBlanc. The series was universally praised for its writing and acting. Friends is a critically and commercially acclaimed series that became a cultural phenomenon. It was nominated for 62 Primetime Emmy Awards and won for Outstanding Comedy in 2002. The series is known for its hilarious and sweet, heartwarming moments. The series has made its fans cry on more than one occasion. Sweet moments like when Monica proposed to Chandler or when Rachel and Ross finally got together. However, other times they’ve made us break down and sob like little babies with some of the most heartbreaking moments in the series. Here is a look at 15 of the most heartbreaking moments from Friends.


15 Joey Misses Chandler


Ross and Rachel had nothing on the deep love between Joey and Chandler. They were opposites in many ways but still had a lot in common. They love to play foosball, sit in their comfy chairs and watch Baywatch. However, things began to change after Chandler married Monica. First, Chandler moved out, which was hard for Joey but later he got a hot roommate so he got over it. Once they got married, Joey and Chandler spent less time together. In the season 8 episode “The One With the Stripper”, Chandler finds out that Monica had a bachelorette party when they had agreed not to. Monica hires a stripper for an impromptu bachelor party, which is only attended by Chandler and Joey. However, it turns out that the stripper is actually a prostitute. Joey and Chandler argue over who is going to tell the prostitute to leave. It’s at that point that Joey reveals that he misses Chandler. They have a heart to heart with Joey explaining how he feels and that things aren’t like they used to be. He understands that things have changed for Chandler. Chandler comforts Joey and they hug. It’s heartbreaking to see how much Joey misses his best friend but ends on a happy note.

14 Joey Moves Out

There was no love in Friends stronger than the love between Joey Tribbiani (Matt LeBlanc) and Chandler Bing (Matthew Perry). They were best friends and roommates from the start of the series. Joey was a struggling actor and Chandler sometimes had to help him out with money. Joey was a ladies man and Chandler would need help with that. However, Joey landed a job on Days of our Lives and no longer needed to rely on Chandler. Joey decided to move out but Chandler was a little saddened that his best buddy wanted to leave. It caused a rift between the two friends and for a while weren’t really getting along with each other. Chandler was deeply hurt that Joey was moving out but it was something Joey felt he needed to do. He grew up in a large family and had never lived on his own. In the season 2 episode “The One Where Joey Moves Out”, Joey realizes it’s time for him to become more independent. In a heartbreaking moment, Joey and Chandler say goodbye to each other and Joey moves out, giving each other one last hug. Later, Joey would move back in with Chandler and the bromance would continue.

13 Phoebe And David Break Up

Phoebe Buffay (Lisa Kudrow) had gone through a lot of heartbreak throughout the series. Her first love was scientist David (Hank Azaria). In the season 1 episode “The One With The Monkey”, Phoebe meets David at Central Perk after confronting him and his friend. They were talking while she performed but it turned out they were talking about how beautiful she is. They instantly get along with each other and start to fall in love. However, David is offered a job in Minsk and he was forced to choose between being with Phoebe and following his dream. He initially chose to stay with Phoebe but Phoebe quickly realized that he had to go. In one of Phoebe’s first moments of heartbreak, Phoebe made David break up with her and go to Minsk. He returns later but not to stay. He returned again in season 9 but Phoebe was going through a tough time after her breakup with Mike. David attempted to propose to Phoebe in Jamaica but Mike showed up to do the same. Phoebe and David were just not meant to be.

12 Phoebe Finds Out That Joey Slept With Ursula


Phoebe and Joey had a special friendship. There was never anything romantic between them but they had a deep understanding of each other. Joey was always the ladies man who was known to break hearts. Phoebe had an identical twin sister, Ursula (Lisa Kudrow), who worked at a Riffs, which was featured in Mad About You. Phoebe and Ursula never had a good relationship and were estranged for the most part. Joey meets Ursula and falls for her right away in the season 1, two part episode, “The One With Two Parts: Part 1 and Part 2”. He’s never seen anyone so beautiful before… well, unless you count Phoebe. Phoebe was against Joey dating Ursula and even thought that she had gotten through to him. She was concerned for Joey more than her sister. The heartbreaking moment comes when Phoebe goes to Joey’s and Ursula opens the door. Phoebe’s reaction is a combination of feeling betrayed and disappointment in her friend.

11 Ross And Rachel Can’t Be Friends

Ross Geller (David Schiwmmer) and Rachel Green (Jennifer Aniston) seemed destined to be soulmates, but there was always something preventing them. They broke up and both seemed to move on. However, Ross had a tougher time moving on. That all changed when Ross got engaged to Emily (Helen Baxendale). They had only known each other for a short period of time. Rachel thought she had moved on but realized she was still in love with Ross. Ross and Emily were getting married and everyone but Phoebe and Rachel went to the wedding in England. At the last minute, Rachel decided to go and chaos ensued. During the wedding, Ross said Rachel’s name instead of Emily's at the altar. Ross tried to work things out with Emily but she agreed to try to make things work only if he stopped being Rachel’s friend. Ross struggled with the decision until he got some advice from Rachel. She was unaware of what was happening but told Ross to do whatever it took to get Emily back. Initially, he chose to end the friendship with Rachel and be with Emily. In the end, Ross refused to give up his friendship with Rachel and lost Emily because of it.

10 Rachel’s Goodbye

In the final season of Friends, there was one major burning question. What’s going to happen between Ross and Rachel? They are the ultimate “will they or won’t they?” couple. However, at that point they were not together but had a child together. Ross started to realize that he wanted to be with her but like always, something got in the way. Rachel was offered her dream job, which happens to be in Paris. In the season 10 episode “The One With Rachel’s Going Away Party”, Rachel says goodbye to each of her friends one by one. Each goodbye is more heartbreaking than the other. Rachel and Monica share tears and have an inaudible goodbye. Phoebe gives Rachel a lock of her hair. Chandler tries not to make any jokes and Joey tries to jump off the building. The most heartbreaking was her goodbye to Ross. It was so hard for her to say bye to Ross that she didn’t. It led to Ross confronting her which resulted in them sleeping together. In a very memorable scene, Ross tried to stop Rachel from leaving but she got on the plane. However, it ended on a happy note when Ross returned home and listened to a message she left for him. Ross turned around and Rachel was standing in the doorway.

9 Phoebe And Mike Break Up

Phoebe and Joey agreed to go on a double date. They would each find a date for the other. Of course, Joey forgot and randomly picked a guy from Central Perk. He convinced a stranger, Mike Hannigan (Paul Rudd), to go on a blind date with Phoebe. Luckily for Joey, Mike and Phoebe eventually felt a connection and fell in love with each other. They started to spend all their time together and realized that they might as well move in with each other. In the season 9 episode “The One With The Boob Job”, Phoebe and Mike begin the process of moving in together. During the move, Phoebe and Mike address the fact that Mike doesn’t want to get married because he just went through a tough divorce. It got to the point that Phoebe realized that she wanted to get married but Mike was totally against the idea. In a heartbreaking moment, Phoebe and Mike breakup despite their strong love. Luckily for us, later they reunited and get married in one of the most memorable weddings from the series.


8 Rachel Rejects Joey


Joey never seemed like the type of guy to settle down. He was focused on his acting career. He was known for being a ladies man and got just about any woman he wanted. He was best known for his catchphrase, “How you doin?” However, everything started to change for Joey when Rachel moved in with him. He was there for her during her pregnancy and started to develop feelings for her. However, he tried to fight those feelings for her because of her long history with Ross, who was also the father of her child. Joey’s feelings for Rachel were becoming too much for him to handle and Ross was feeling left out. This led Joey to convince Rachel to move in with Ross. That didn’t stop Joey from feeling the way he felt. In the season 8 episode “The One Where Joey tells Rachel”, he finally told her how he felt and that he was in love with her. Unfortunately for Joey, Rachel didn’t feel the same way and rejects him in a very loving way. It clearly broke both of their hearts. Later, they would attempt to date but it doesn’t work out for them. It's clear that Joey and Rachel are meant to be great friends.

7 Phoebe Meets Phoebe

Phoebe had a very tough childhood. Her mother committed suicide and her father ran out on her. At a time she was homeless but learned how to take care of herself. She managed to track down a friend of her mother and father’s from their younger days also named Phoebe (Teri Garr). In the season 3 episode “The One at the Beach”, the gang goes to the beach and Phoebe searches to find her parents' former friend. She hopes that she will able to help Phoebe find her father. Phoebe tries to connect with her mother’s BFF but it’s clear that she knows more then she’s revealing. Phoebe discovers a picture that she believes is of her father, but is in fact not. However, Phoebe soon finds out that this new Phoebe is her real mother and not just her mother's friend.

In the season 4 premiere “The One With The Jellyfish”, Phoebe tells her real mother the pain and loneliness she has felt in her life. She’s both devastated and heartbroken that she was lied to and that her real mother never tried to reach out to her. Later, her real mother apologizes and they try to work things out.

6 Monica And Richard Break Up On The Dance Floor

Before Monica Geller and Chandler fell in love they were both out there searching for love. Monica was first in love with Dr. Richard Burke (Tom Selleck). Richard was 21 years older than Monica and was actually her childhood eye doctor. Monica thought Richard was her soulmate. Monica wanted to spend the rest of her life with Richard and wanted to have children. However, Richard had previously been married and had children roughly Monica’s age. Richard would gladly marry Monica but he didn’t want to have more children. In the season 2 finale “The One with Barry and Mindy’s Wedding”, Richard and Monica attend the wedding. In a very heartbreaking but subtle moment, Monica and Richard breakup. This occurs while on the dance floor and they’re discussing their future. They realize their future is not together and agree to break up. They continue to dance one last time.

5 The Prom Video

via:Dog Star Omnibus

It wasn’t easy for Ross and Rachel to end up together. First Ross liked Rachel but she had no idea. When she found out, she developed feelings for him but he was dating someone else. They almost get together but Rachel discovers a list that Ross made comparing her to his then girlfriend, Julie. For a while it seemed that they’d never end up with each other. That all changed in the season 2 episode “The One With The Prom Video”. The episode featured the gang watching an old home video of Monica and Rachel getting ready for their prom. Ross objected to watching the video. In the video, Rachel’s date for the prom, Chip, stands her up. She’s devastated and decides not to go. Ross is back from college visiting, and his parents convince him to take Rachel and surprise her. He agrees and puts on his dad’s tuxedo. In a heartbreaking moment, Ross stands at the top of the staircase waiting to surprise Rachel only to discover that Chip had shown up. Ross is left standing there without anyone. In the present, Rachel is so touched by the heartbreaking moment from the prom video that she kisses Ross.

4 Monica And Chandler Can’t Have Babies

Monica and Chandler’s love has made us laugh and cry tears of joy. They’ve also broken our hearts and this is one of the more difficult ones. Monica had always wanted to get married and start a family. It even led to her breaking up with Richard because he didn’t want to have kids. Monica and Chandler were married and wanted to start a family. They went through many ups and downs. They struggled to have children so they went to a fertility doctor. In the season 8 episode “The One with The Fertility Test”, Chandler and Monica find out they are unable to have kids. In a very heartbreaking moment, Chandler tells Monica that the doctor informed them they couldn’t have babies. They comfort each other but it’s clear that both of their hearts are broken. It’s an incredibly sad moment in the series. However, later they decided to adopt a baby and end up having twins.

3 Ross And Rachel Break Up

Ross and Rachel were the ultimate “will they or won’t they?” couple. Fans tuned in every week to see the latest chapter in the Ross and Rachel saga. They went through a lot of obstacles to get together. However, things wouldn’t be all rainbows and sunshine. They started to have problems mostly because Ross was jealous of Rachel’s professional relationship at work. They were fighting a lot and Rachel felt that they needed a “break”. This would cause great confusion with Ross who believed them to be broken up.

In the season 3 episode “The One where Ross and Rachel take a break”, Ross cheats on Rachel and when Rachel finds out in the next episode, her heart was broken. She wasn’t the only one. In the episode “The One with the Morning After”, Ross tried to fix things with Rachel, while Monica, Joey, Chandler and Phoebe were locked in Monica’s room listening in. Ross is desperate to resolve the issue but in the end of the episode Rachel officially breaks up with Ross. Rachel cried, Ross cried and we all cried. It’s widely regarded as one of the most heartbreaking moments in the series.

2 The Series Finale

Friends is considered by many to be one of the best sitcoms ever. The series had a huge impact on society, so much so that Rachel’s hairstyle would be copied by many and dubbed “The Rachel”. Several of their sayings have become commonplace, such as, “How You Doin?” and “Pivot!” The series was on the air for 10 seasons and it made us laugh, cry and broke our hearts. There were several heartbreaking moments but one of the most difficult happened at the very end. The series finale, “The Last One”, was possibly one of the most emotional series finales of any sitcom. The final scene in the series finale has all 6 friends standing in Monica and Chandler’s empty apartment. The scene is incredibly emotional as all of them are about to go their separate ways. However, deeper than that is the fact that the series would be over. Not only were they going their separate ways but also, we the viewers, were going our separate ways. The scene was so emotional that Jennifer Aniston is seen fighting back the tears. She even stated that she was so sad that she tried to hide behind David Schwimmer to hide her crying.

1 Phoebe’s Goodbye To The Triplets

It’s not only one of the most heartbreaking moments in Friends, but it’s also one of the most heartbreaking moments in TV history. During season 4, Phoebe’s brother, Frank (Giovanni Ribisi) and his wife Alice (Debra Jo Rupp), asked her to do them a huge favor. They asked Phoebe to be their surrogate because of difficulties they faced conceiving a child. She agreed and gave birth to triplets in the season 5 episode “The One Hundredth”, also known as “The One with the Triplets”. During her pregnancy she became very attached to the triplets and wanted to keep one. She hoped that Rachel could convince Frank to let Phoebe keep one. However, in the end she knew that the right thing to do was to not stand in their way. In a very heartbreaking moment, after giving birth Phoebe asks her friends to leave her alone with the triplets. She holds the triplets in her arms and says goodbye. She breaks down in tears as she holds them.


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