- A brief one when Ross admits he kissed Nora Bing. Chandler looks so betrayed, dropping the telling comment that Ross knows better than anyone "what I go through with my mother"- It's a rare occasion when his troubled childhood isn't played for laughs.
- After Rachel finds out about Ross's feelings for her in "The One Where Rachel Finds Out" and realizes she feels the same way, she decides to meet him at the airport as he comes back from his week long archeological dig in China, only to find Ross getting off the plane with his new girfriend Julie.
- 'TOW with the List' when Rachel finds out about said list, and is nearly crying when she explains she already hates those things about herself, and to find out Ross thinks they're her flaws is too much.
- 'TOW the Flashback' when Ross finds out about Carol being a lesbian and starts sobbing in Phoebe's arms. His divorces are usually Played for Laughs but the scene really shows how devastated he was at the time.
Ross: "She was the only woman who ever loved me..."
- Just seeing how crushed Ross looks at the end of the tape the gang is watching in "The One With the Prom Video" where he attempted to take Rachel to the prom after it looked like her date abandoned her so she wouldn't have to miss it, only to learn that the date arrived at the very last second.
- Earlier on, when Rachel tells Ross his love for her isn't worth getting "clobbered" over. One of the worst things you can hear from the one you love is that your love isn't worth fighting or getting hurt over.
- While 'TOW The Cat' is pretty derided as an episode, Lisa Kudrow's delivery of "Ross, how many parents have you lost?" almost makes it worth it.
- In “TOW Joey's New Girlfriend”, while the sting is lessened by Joey not getting it, Chandler's rant about how slit-his-own-throat-in-love he is with Kathy.
- 'TOW The Truth About London' Chandler's reaction when he finds out Monica initially wanted to sleep with Joey instead of him. As he's always been second best to Joey and an Insecure Love Interest with Monica, the news is shattering for his already fragile self-esteem.
Chandler: "How can I not be upset? Okay? I finally fall in love with this fantastic woman and it turns out that she wanted you first!"
- When Ross, Joey & Chandler are at the veterinarian's office because the duck ate Ross's grandmother's ring, they imagine all the history with the duck, as a montage of the duck plays backed by "Weekend in New England" by Barry Manilow. The guys' affection for the duck makes the montage more touching than it is funny.
- Monica and Richard's break-up in "The One With Barry And Mindy's Wedding". They are perfect together, but he doesn't want to have kids... And Monica longs for them. It's such a painful situation that nearly everyone can empathize with—being in a nearly-perfect relationship except for that one thing, a dealbreaker that neither person can/will/should compromise on.
- Also how depressed Chandler looks when he discovers that the girl online (Janice) he's in love with to the point of freaking people out with his not making jokes, is actually married. Even his Big Damn Kiss with her at the end is played more needy than romantic.
- “TOW Poking Device”: Joey having to tell Chandler (who wanted to buy Janice pearls for her birthday) that Janice was kissing her ex husband. Also Janice's sad “I don't know” when he asks her which man she loves more, him or her husband, plus the break-up where first he tells her he doesn't want to break up a marriage and then he changes his mind and begs her not to leave.
- The One In Vegas: Chandler and Monica get into a fight about her seeing Richard. Chandler comes to make up...only to find her happily gambling and seemingly not missing him at all. (She'd actually been depressed all evening but he doesn't know that). The mixture of regret and hurt in his reaction, complete with a bitter, defeated smile, makes the one scene heartbreaking.
- Made worse later when they talk and he says that Richard is the love of Monica's life. You realize that seeing Monica apparently so blase about their fight just reinforced his belief that he was always going to come second to her. He walked away because he honestly believed she didn't care about him as much as he cared about her. Oh yeah, and this is their anniversary; meaning he'd been carrying around these assumptions for several months and apparently accepted being runner up to the first woman he'd ever truly loved. When Monica sorts it out you want to cry with relief.
- Fun little fact: that aforementioned talk? Happened after Monica noticed Chandler walk past with his suitcase and was leaving... although it's made better when we learn Chandler never bothered to pack it, mainly because he wanted to make a scene but hates packing.
- Rachel finding out about Ross sleeping with Chloe the copy girl in "The One On The Morning After" and their massive fight and break-up afterwards is one of the most devastating and gut-wrenching moments in the entire series.
- Arguably made worse by the funny scenes sprinkled throughout the episode and even well into the prolonged argument immediately preceding the breakup. Someone who doesn't know any better could be forgiven for taking the lightheartedness as a sign that everything would be okay by the episode's end.
- This was so devastatingly dark for Friends that the creators themselves vowed to never make a scene as depressing as their breakup for the rest of the series' run.
- TOW The List:
Chandler: What's wrong with [Julie]?Ross: ... She's not Rachel.
- Phoebe says goodbye to the triplets:
"I wish I could take you home and see you every single day... well, if you're going to cry... (starts to cry)"
- And prior to that, when Rachel tells her she can't keep one of the babies. The look on Phoebe's face is crushing.
- Almost the whole of 'TOW the Last Night' when Chandler and Monica move in together. They're happy they're moving forward, but have to say goodbye to Joey and Rachel who have been their roommates for the last 5+ years. It's a surprisingly touching episode that shows how even good change can be hard.
- TOW The Lottery when Chandler finds out he didn't get the advertising job. He's clearly crushed and quietly admits to Monica that he really thought he deserved it. After years working a job he hated, him failing in a career that he's actually passionate about is extremely sad. Previous episode also hinted he was depressed and losing confidence at being unemployed and Monica having to support him. (Thankfully, this is all undone when he finds out he got a much better position as junior copywriter).
- TOW Chandler's Dad is a sober episode. Although Played for Laughs, Chandler is obviously still insecure from his dad's treatment of him and you can see Charles' sadness when he hears his son is getting married and hasn't invited or even told him. (Especially as Chandler admitted Charles tried to get in touch with him in the last few years).
- Again played for laughs but Chandler's freak out before the wedding is pretty sad. Especially when he admits to Ross and Phoebe how much he loves Monica but can't get married because he's going to be a terrible husband. Given he and Monica have been nothing but happy together you realize how deep seated his anxieties and childhood trauma's really are.
Chandler: "I want to. I love her so much, but I’m afr... It’s too huge."
- When Chandler thinks Monica has left him (just before he was going to propose). She hasn't, but for a moment he breaks down sobbing, and its absolutely heartbreaking.
Chandler: I can't believe I ruined this. I can't...
- Played for Laughs but in TOW Rachel's Date, there's a rant about how "you're better than Chandler, we're all better than Chandler". Chandler's the one saying it by the way, and it's just sad that his self hate hasn't gone away even after marrying Monica, despite being arguably the most successful of the group.
- Chandler and Monica finding out that they might not be able to have children in "TOW the Fertility Test" makes for one of the most devastating moments in the series.
Chandler: Apparently my sperm have low motility and you have an inhospitable environment.Monica: Oh... What does that mean?Chandler: It means that my guys won't get off their barcaloungers and you have a uterus that is prepared to kill the ones that do. It means-Monica: Chandler...?Chandler: It means that we can keep trying, but there's a good chance this may never happen for us.Monica: (starts to cry) ...Oh my God!Chandler: I'm sorry.Monica: I'm sorry too.(they both hug)Chandler: Well, we're gonna... we're gonna figure this out.Monica: (tearful) I know.
- It's made even worse when you realize that none of the friends are ever shown supporting, sympathizing with, or even talking about it with them on-screen (except for maybe Joey).
- Chandler at the end of TOW Heckles Dies: "Goodbye, Mr. Heckles. We'll try to keep it down." Chandler throughout the whole episode really. While he ends up okay, his driving himself into a fit about being abandoned by the others is sadly relatable, and his Hates Being Alone side keeps popping up in the background for the rest of the season.
- Anything when Matthew Perry uses his considerable acting chops to make us cry instead of make us laugh. Like when he tells Erica, the birth mom, that when his chance comes, he'll step up and be a good dad. Considering the contextual information regarding the cast's notoriously close friendship and Courteney Cox's well reported battle to have a baby in real life, that line must have meant a lot to him.
Chandler: But my wife? She's already there. She's a mother without a baby.
- Rachel leaving for Paris and saying goodbye to each of the friends individually. Fortunately it is saved when she and Monica start comically whimpering incoherently at each other.
- Rachel telling Ross that the reason that she didn't say goodbye to him was because it was too difficult.
- The series finale has several emotional moments, but their are a couple that really stand out. While we all know Rachel gets off that plane, her initial rejection of Ross at the airport and his breakdown after it are incredibly heartbreaking.
- The last episode, particularly the final moments of the show, when they are all in the apartment saying goodbye and leaving their keys on the side. Courtney Cox's exact line is: "This is harder than I thought it would be." She didn't need to act very much to get the emotion there. The writers specifically mentioned that Matthew Perry found his response: "Its going to be ok" incredibly hard to deliver comfortingly because in many ways it wasn't going to be ok or at least not the same. Whatever your feelings towards Friends, for them it was still ten years of working together, and by all accounts being fantastic friends. All the emotion comes across in the final episode, and it breaks your heart.
- Lisa Kudrow's voice breaks in practically every line in the last scene ("Do you realize that at one time or another we've all lived in this apartment?") and after her line "So I guess this is it", Matt Le Blanc says "Yeah," pauses to give a subtle glance/nod to the audience, and then says the rest of his line, "I guess so." It's heartbreaking.
- Another subversion, but in the closing minutes of "The One Where Ross Finds Out", right before Ross and Rachel have their first Big Damn Kiss, the two share a very dramatic confrontation where they each call each other out on either revealing or holding back their feelings for each other. It's particularly stinging at the end, when Ross gives the impression that a relationship between the two of them is no longer an option. Thankfully, the last few seconds make it one of the series' Crowning moments of Heartwarming and Awesome simultaneously.
Rachel: Do you even have a point?Ross: The point is that I-I don't need this right now. OK? It's too late. I'm with somebody else. I'm happy. This ship has sailed.Rachel: Okay, so what're you saying? You're just going to put away feelings, or whatever the hell it is you were feeling for me?
- And while she's treated him badly (because she needs a project after getting fired) all episode, Monica steadily looking more destroyed as Chandler tears her down by listing everything that's going wrong with her life is painful to watch. It's a rather chilling demonstration of how petty and spiteful he could be pre Character Development and incredibly harsh from one of the nicest characters on the show. Especially as Chandler's all too aware of Monica's insecurities and later seasons have them mutually supporting each other through their self-doubts.
- In TOW The Candy Hearts, Ross sees Carol and Susan at a restaurant on Valentine's Day while he's there with a date. After Susan gets buzzed in to go to work, Carol is left by herself and Ross invites her to come sit with him and his date. They end up having a nice conversation and Ross doesn't even notice when his date leaves. Pleadingly, Ross futilely asks Carol to give it one more try with him. Carol gives him a kiss and tell him she'll always love him . . . but that the one thing that has to be put to the side to make it work won't go away. It's heartbreaking to see that Ross, after all this time, still sees Carol as the woman he loves, even with Rachel around, and that he seems to want to make their incompatible relationship work just to get some normality back into his life..
- In spite of the infamous Joey-Rachel storyline, the growing guilt Joey had over how he felt he was completely betraying Ross was pretty heartwrenching. A particularly stinging moment is in TOW the Secret Closet where Joey is mistaken for the father of Ross and Rachel's baby. Ross, who has already been missing several bits of her pregnancy especially the baby's first kick, winds up feeling even worse, and Joey meanwhile feels like even more of a louse. It's hard not to feel bad for both of them.
- When Phoebe and Mike decide to not just end moving in together, but also their relationship. Considering the rarity of dramatic moments for these characters, both of them being really affected by the abrupt ending of their relationship despite being deeply in love with each other is pretty heart-wrenching. Fortunately, they got better.
- In TOW Rachel's Date, Ross is acting possessive, pushy, and...well, like he did when he had feelings for Rachel. So that's it, right? He has a crush on Rachel again, and the whole cycle starts again, right? ...Nope, not even close. In fact, he confesses that he's done trying to force himself to fall in love with Rachel. What he's actually anxious about is that his dream of having a real family is slowly moving farther away. He confesses that it kills him that he has to let go of his son and return him to his mother and her lover, and it utterly terrifies him that Rachel might go off with someone else, taking Emma, and having a family with said person instead of him. Sure, Ross has his bad moments, but this scene reminds us that he has had his dream of not just a romance but a complete, functioning family broken repeatedly over the course of the series.
- The storyline of Ross and Emily trying to reconcile their differences that runs between "TOW Phoebe Hates PBS" and "TOW The Kips". Ross being so desperate to see Emily is bad enough, but she agrees to see him... under the condition that he doesn't see Rachel ever again. Though it's understandable why she'd feel that way after "TOW Ross Says Rachel", but Ross is clearly allowing himself to be trapped in a toxic relationship that clearly wasn't meant to be. When Joey correctly tells him he married too fast, you can't help but agree.
Rachel: Well, for starters, I would have said the right name at my wedding.
- Particularly Ross and Emily's last conversation, where he asks her if she can trust him, and after a long pause, she finally says in this teeny-tiny voice, "No". As badly as Emily has acted throughout this whole thing, you can't help but be very sad for both of them as they come to the painful realization that their marriage can't work and is over before it could even begin.
- In 'TOW The Bag', until it turns heartwarming, Phoebe's scene with her father. First she's trying to give him outs to prove he didn't just abandon the family, and then she has to tell him his wife and her mother is dead.
- In 'TOW Rosita Dies', it's revealed that Monica's dad had accidentally used boxes of her childhood possessions to protect his Porsche from a few inches of water, destroying the contents. Though he realizes the seriousness of what he did, it underlines just how little regard Jack and Judy have for their daughter's feelings. After years of jokes about Monica being second-best to them, seeing the remnants of her childhood molding and crumbling by Jack's own apathy is exquisitely painful to watch.
- In TOW The Tiny T-Shirt, Ross is forced to come to terms with the fact that Rachel is moving on from her relationship with him. Chandler's words ("It's over, man. It's over.") are all too real to someone who's endured a painful breakup.
- From the same episode, Joey looking dejected when he realizes his love interest Kate is with the director of the play they're starring in.
- Kathy's goodbye to Chandler who's "living in the box" about how she doesn't want to break up their (Chandler and Joey's) friendship. And then we just see one of Chandler's finger sadly (somehow) come up out of the little air hole in the box and wave goodbye.
Tear Jerker / Friends
While Friends is usually a very light hearted and optimistic show, it's had a few notable examples.