The 12 Saddest 'Friends' Moments Ever — Yes, Including The Prom Video

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Friends is widely considered to be one of the greatest television comedies of all time. Over 10 seasons on NBC, the popular sitcom produced countless laughs thanks to the witty sarcasm of Chandler, the absent-mindedness of Joey, and the charming oddness of Phoebe, among other things, but what set Friends apart from its competition was its ability to get emotional, too. Fans came to love these characters, and when things didn't go well for them, the outcomes could really hit the audience hard. So hard, in fact, that there are a number of sad Friends moments that'll make you cry.

Now the key word here is "sad," as there are plenty of other tear-worthy moments from the series that don't really qualify as sad. Ross and Rachel's first kiss at Central Perk? Happy tears. Monica proposes to Chandler? More happy tears. Rachel gets off the plane? Still more happy tears! Honestly, there are enough happy tears moments from Friends to fill a whole other list, but that's not the purpose of this article. This piece is all about the truly sad moments of Friends, and the 12 examples listed below all have the potential to make you cry actual tears of sorrow instead of tears of joy.

The Prom Video

Ross is, admittedly, kind of a major jerk throughout most of the series, but apparently he was a sweet guy in college. This flashback video shows his willingness to accompany Rachel to her prom after her date Chip doesn't show up, only to end up disappointed when Chip eventually makes an appearance and whisks Rachel away, leaving Ross literally all dressed up with no place to go.

Ross & Rachel's Breakup

Oof. The first breakup of Ross and Rachel is intense and heartbreaking, mostly because it feels so real. After Ross sleeps with someone else while he and Rachel are on a break (a break of less than one day, mind you), Rachel breaks up with him despite still being in love with him.

Monica & Richard's Breakup

Another breakup, this one is far less intense but no less heartbreaking. Richard and Monica were great together, but they were just at different stages in their lives, and that reality brings their relationship to an end while sharing a dance at a wedding, of all places.

Phoebe & Mike's Breakup

OK, this is the last breakup, I swear. Phoebe looked like she was finally going to get her own bit of happiness here while moving in with Mike, but like Monica and Richard before them, the two of them realize they wanted different things in life at a very inopportune time. Although this breakup was super sad, Phoebe did eventually get her happy ending when she got back together with Mike and later married him.

Phoebe Having The Triplets

After giving birth to her brother's triplets (don't ask), Phoebe gives a very emotional goodbye to the three newborns after realizing that she wasn't going to be able to raise them since they weren't technically her kids.

Phoebe Meeting Her Dad

Phoebe meets her father for the first time and learns the origins of "Smelly Cat" in this tear-jerking scene where Lisa Kudrow once again shows off some serious dramatic acting chops.

Phoebe's Speech About Her Cat-Mom

Boy, for a silly character Phoebe sure does have a lot of super sad moments. Throughout this episode, Phoebe believes a stray cat she finds is the reincarnation of her dead mother, and the speech she gives to Ross about losing a parent when he tells her it's just a cat (typical Ross move) is seriously powerful.

Ross Saying Goodbye To Marcel

Ross' most meaningful relationship on the series was with his pet monkey (it's true), and seeing him say goodbye to the furry little fella will strike at the heart of anyone who's ever lost a pet.

Mr. Heckles Dying

Mr. Heckles was hardly an important character on Friends, but he sure did get one emotional sendoff. After the gang's downstairs neighbor dies, Chandler discovers that he was kind of a kindred spirit to the old curmudgeon — and fears that he'll suffer a similar lonely fate. The end of the episode, with Chandler saying his last goodbye to Heckles, is where the waterworks really kick in.

Joey Finding Out About Chandler & Kathy

The friendship between Joey and Chandler was mostly unshakeable, but when Joey finds out that Chandler stole his girlfriend Kathy, it looked like their friendship could be over for real — and the conflict wasn't even resolved in this episode!

Chandler & Monica Finding Out They Can’t Have Kids

Holy moly is this heartbreaking. With both Chandler and Monica learning they're infertile, it looked like they would never fulfill their dream of starting a family. It of course worked out in the end when they adopt, but still, this is a very sad and real moment for any sitcom.

The Empty Apartment

The series' final scene is arguably its saddest. Seeing the apartment where so many laughs and memories took place over ten years completely emptied out is a major gut punch, and it still serves as a reminder that there will never be another new episode of Friends.

These moments prove that Friends wasn't just one of the all time funniest sitcoms, it was also one of the saddest, and that's a big part of the reason why it remains so popular today.