Friendsis one of the most iconic sitcoms of the 1990s which captivated audiences around the world with its six endearing characters and their ever-changing lives. Set in New York City, the series follows friends, Ross (David Schwimmer), Rachel (Jennifer Aniston), Monica (Courteney Cox), Chandler (Matthew Perry), Joey (Matt LeBlanc), and Phoebe (Lisa Kudrow), as they try to navigate their way in the world and adapt to the major life events that most people experience at some point in their lives.
From break-ups to landing dream jobs, each friend goes through an array of ups and downs, but no matter what the situation may be, they’re always there to pick each other up as well as celebrate their personal victories. Even though the show is essentially a comedy, it still has some memorable sad moments, such as Monica and Richard breaking up and Joey moving into his own place. Out of all the unforgettable tear-filled moments in the show, these are the saddestFriendsepisodes.
10"The One With the Boob Job"
Season 9, Episode 16
As Mike (Paul Rudd) and Phoebe’s relationship continues to progress, Phoebe takes a big step and asks Mike to move in with her, which he happily agrees to. While they start the moving process and prepare for the next chapter, the discussion of marriage and their future comes up and reveals that the couple is not exactly on the same page. When Mike tells Phoebe he never wants to get married again, Phoebe can’t deny she doesn’t dream of tying the knot and the two decide to break up.
In season 9, episode sixteen, “The One With the Boob Job,” fans are thrilled when Mike and Phoebe decide to move in together, as they were considered to be one of the best couples in the series. Even though both of them come from completely different worlds, they just seem to fit so well together, so it’s understandable how heartbroken fans were when they made the difficult decision to end their relationship.Considering how far their relationship had come, and being so close to making that next major milestone, all to be shattered in the blink of an eye makes this one of the saddestFriendsepisodes.
9"The One with the Fake Monica"
Season 1, Episode 21
When Ross' pet monkey, Marcel, begins to exhibit unruly behavior, Ross learns that the best thing for Marcel is to find him a home in a zoo where he can be with other monkeys. As Ross submits applications to several zoos (almost like Marcel is applying for college), he finally receives a letter from the San Diego Zoo, which is willing to take Marcel. While it’s the best scenario for Marcel, that doesn’t mean it isn’t difficult for Ross to say goodbye to his friend.
The departure of Marcel in season 1, episode twenty-one, “The One with the Fake Monica,” is one of the saddest episodes inFriends, as Ross continues to struggle with his divorce from Susan and being a part-time dad to his newborn son. Even though Marcel had his moments of being a pain in the butt, he did bring some sense of happiness to Ross, so as he and the others say goodbye to Marcel at the airport, it’s hard not to feel the tears welling up.Even though Marcel wouldn’t have made a great pet long-term and this was for his benefit, it’s still a downer to see Ross in such a sad state, which is why this is one of the saddest episodes in the series.
8"The One With the Monkey"
Season 1, Episode 10
While Phoebe is performing at Central Perk, she abruptly chastises two men who are whispering during her performance, demanding to know what is so important that they can’t wait until after to talk. To Phoebe’s surprise, one of them, David (Hank Azaria) explains how he was telling his friend, Max, how beautiful Phoebe was, resulting in Phoebe cutting her performance short. As David and Phoebe are caught up in a whirlwind romance, their bliss is destroyed when David and Max receive a grant to conduct research in Minsk, Russia.
Phoebe has always been the kind of person who deserves the best, so when she meets David in season 1, episode ten, “The One With the Monkey,” audiences think she’s finally found someone but quickly dash their hopes by sending the poor guy off to Russia. Even though David initially decides not to go, Phoebe, being the gem that she is, knows she can’t be the reason why David stays and eventually convinces him to go.As soon as Phoebe finds her match, the universe unfairly steps in, but despite the devastating choice, it reveals how selfless and considerate Phoebe truly is and puts her at the center of one of the series' saddest episodes.
7"The One With the Invitation"
Season 4, Episode 21
As Ross and Emily (Helen Baxendale) plan their upcoming wedding, Ross is unsure if he should invite Rachel considering their romantic history but he eventually decides to send her an invitation. When Rachel receives the invite, she too becomes conflicted about the whole event and struggles to decide if she should RSVP or not. Through a series of flashbacks of their relationship, Rachel finally makes the decision not to go.
The terrible timing of Ross and Rachel is a constant theme throughout the series, but when Ross is about to get married, it puts things in a different light, presenting the question: is this the end of them? In season 4, episode twenty-one, “The One With the Invitation,” audiences look back on their relationship, which only solidifies how the two essentially belong together.Even though Rachel doesn’t realize she’s still in love with Ross, fans can tell this just by her choosing not to attend the wedding, which cements this episode as one the saddestFriendsepisodes.
6"The One Where Heckles Dies"
Season 2, Episode 3
When Rachel and Monica’s downstairs neighbor, Mr. Heckles (Larry Hankin) unexpectedly dies, they’re surprised to learn that he left everything to them in his will. As the friends go through all of the man’s belongings and random trinkets, Chandler realizes he and Heckles have way too many things in common, causing him to panic and believe that he will end up just like their former neighbor.
Season 2, episode 3, “The One Where Heckles Dies,” isn’t short of comedic moments but as Chandler discovers more about Heckles, the more audiences know more about him and how sad of an existence he truly lived. When he was younger, it seems as though Heckles had everything going for him but somewhere along the line, things went south for the guy, which is incredibly sad for anyone to experience. It’s one thing to die alone, but to die feeling as though you missed out on life is a tragedy in itself.Between Chandler’s dramatics and giving Heckles a bit of an insightful (but depressing) backstory, this episode ranks as one of the saddest episodes in the show.
5"The One With Barry and Mindy’s Wedding"
Season 2, Episode 24
When Monica decides to ask Richard (Tom Selleck) about their potential future together, she’s thrilled when he reveals that he imagines them married but her happiness quickly disappears when she learns that he doesn’t want to have any more kids. Initially, Monica tries to convince him and herself that she doesn’t need to have children and could be happy without them, but as she continues to think about it, she admits that she can’t imagine her life without becoming a mom, resulting in the two deciding to part ways.
Every fan was rooting for Monica and Richard and in season 2, episode 24, “The One With Barry and Mindy’s Wedding,” it’s safe to say that everyone was as devastated as they were about their breakup. Despite their large age gap,Monica and Richard went together like two peas in a pod and were essentially relationship goals. While it’s understandable why they ended their relationship,it’s still sad to see a promising couple like Monica and Richard end their relationship, especially at a happy occasion like a wedding (even if it is Barry and Mindy’s), which is why it’s one of the saddestFriendsepisodes.
4"The One With the Fertility Test"
Season 6, Episode 21
For about a year, Monica and Chandler have been struggling to get pregnant and, after trying every possible suggestion and method, they make the difficult decision to see a doctor who can hopefully shed some light on any issues. Unfortunately, the test results reveal that the problem lies in both Monica and Chandler, at no fault of their own, revealing they most likely will never be able to naturally conceive children of their own.
It’s no secret that Monica has dreamed about becoming a mom and raising children of her own and in season 9, episode twenty-one, “The One With the Fertility Test,” it seems as though that might never happen to her and Chandler. While the news is not what either of them expected, it becomes the first major test in their marriage and brings them even closer together. Even though there are other options for them to still have kids,the reality of the situation and Monica’s disappointment about never being able to physically carry a baby is a heartbreaking blow, ranking this episode as one of the show’s all-time saddest.
3"The One Where Joey Moves Out"
Season 2, Episode 16
When Joey and Chandler disagree about their individual living behavior (like Joey licking a spoon and putting it back in the drawer), both of them begin to wonder if their living arrangement is still working. After they attend a party at one of Joey’s friend’s apartments, Joey starts to think that he’s too old to still have a roommate and makes the surprising decision to find a place of his own.
Joey and Chandler are a vital duo in the serieswith their comedic banter and antics, which are the highlight of many episodes. When Joey makes the decision to find his own apartment in season 2, episode sixteen, “The One Where Joey Moves Out,” it leaves an emptiness in the hearts of fans, completely changing the dynamic of the best friends. After arguing over Joey’s choice,Chandler eventually accepts it and genuinely wants the best for his friend, but when Joey comes back in to give Chandler a final hug, it cements the episode as one of the saddest moments in the entire show.
2"The One With the Morning After"
Season 3, Episode 16
After Rachel and Ross decide to take a break from their relationship, Ross wakes up the next day and is shocked to see that he’s in bed with another woman. When Rachel calls him and the two decide to get back together, Ross goes to extreme lengths to verify Rachel doesn’t find out about the previous night, but despite his best efforts, word eventually gets back to Rachel, who is utterly crushed.
Whether they were or weren’t on an actual break, season 3, episode 16, “The One With the Morning After,” is one of the most upsetting episodes that, unfortunately, doesn’t have a happy ending. Witnessing Rachel and Ross hash out the incident toes the line of comedic relief, but at the peak of their argument, they both begin to break down in tears. It’s hard not to feel bad for both of them in some sense, but at the end of the day, there is nothing more heartbreaking than when two people who are still madly in love with each other end their relationship because the trust has been broken.Even though Rachel and Ross end up together in the end, the episode is still without a doubt one of the saddest and hardest episodes to watch.
1"The Last One"
Season 10, Episode 17 & 18
In thebest episode ofFriends' final season, “The Last One,” each of the friends embarks on a new adventure in a new place, such as Chandler and Monica becoming parents of not one, but TWO babies and Ross and Rachel FINALLY getting back together. While it’s an absolute joy to see all of them move into the next chapter in their lives together and apart, it’s still sad to watch them move on to bigger and better things in the empty place they used to call home.
Even though the two-part finale brilliantly wraps the show up in a neat, satisfying bow, watching everyone leave the apartment for the last time feels as though audiences are saying goodbye to six friends they have come to know and love. The finale isn’t exactly sad, but it is bittersweet as the show has captured the hearts of millions of fans around the world, but like every good thing in life, it eventually has to come to an end.Despite the ending being an inevitable moment for the show, the finale definitely ranks as the saddest (but hopeful)Friendsepisode of all time.
