History TearJerker / HowIMetYourMother

* Barney's emotional meltdown at the basketball hoop at the end of ''Legendaddy''. To elaborate, he has very recently had his father (who abandoned him when he was six) come back into his life and try to reconnect with him. Barney was hoping his father, Jerry, would be a hard-partying roadie who wasn't capable of being a father, since this would justify him abandoning Barney. However, Jerry has turned out to be a loving dad with two children, including a boy named 'Jerome Junior'. Barney can't handle this, and it culminates into him trying to yank JJ's basketball hoop off the garage so he could have at least some souvenir of a childhood he never got to have. Particularly heartbreaking is this exchange:

[[caption-width-right:350:''Look around, Ted. You're all alone.'']]

* At the end of "Tick, Tick, Tick...t"

** After realizing that Robin has chosen Kevin the look on Barney's face is absolutely '''heartbreaking'''. Then the icing on the cake? Watching him clean up the bedroom he had decorated with rose petals and candles.
** How about the look right after that? Kevin walks in and the look Barney gives Robin says "But I thought..." and then she shakes her head. The despair is so overwhelming that his body language in the next few seconds just shows that he has no clue what to do now. A huge departure from the guy who is usually CrazyPrepared.

* There are two particularly gut wrenching moments in the episode "No Pressure''.

* Barney and Quinn break up because their ridiculously long pre-nup makes them realize they don't trust each other enough for marriage to work.

-->'''Lily:''' You wrote all of these things to say goodbye to, but so many of them are good things. Why not just say goodbye to the bad things? Say goodbye to all the times you felt lost, to all the times it was a "no" instead of a "yes," to all the scrapes and bruises, to all the heartache. Say goodbye to everything your really want to do for the last time, but don't go have one last Scotch with Barney, have the first Scotch toasting Barney's new life, because that's a good thing and the good things will always be here waiting for you.

** First, when she admits she doesn't know how to make scrambled eggs, Loretta snarkily comments that she worries what kind of breakfast Robin will make for her children. Robin informs her she doesn't have to worry about that and walks out, clearly close to tears. (It's even worse when you consider that Robin had every reason to believe Loretta already knew about her infertility, and might've thought this was an intentional jab at it, even though it wasn't.)

* In "Unpause", Lily and Marshall's fight over Marshall accepting the judgeship - Lily refuses to give up her dream or even discuss the judgeship, whilst Marshall tries to convince Lily it's what's best for their family & that they should at least discuss it, despite already taking the job behind her back. The fight reaches its climax when Lily claims that she's never been as selfish in their relationship as Marshall is right now, only for Marshall to counter by bringing up her breaking off their engagement less than two months before the wedding so she could try & become an artist in San Francisco. Lily is left absolutely speechless as Marshall brings up the worst thing she ever did to him, for the first time in 7 years. Since they've had so few on-screen fights, it's particularly jarring to see things escalate so far in so little time.
** Even worse, we learn that Marshall secretly fears the only reason Lily came back to him was because she failed in San Francisco, and when he asks her all Lily can do is run out of the room in tears.

* The Mother's back story. We find out she was in love with this one guy who died the same night Ted met Robin. For the next eight years, she never lets herself fall in love again because she can't let him go, just like [[FridgeBrilliance Ted with Robin. Her speech to her dead boyfriend when she realizes this and starts to breakdown is heart-wrenching.]]

** As a part of that same episode, the Mother playing Edith Piaf's ''La Vie En Rose'' on the ukelele her dead boyfriend gave her, while cutting to the various main characters at this point in the show. It's really quite moving, to say the least.
** The sheer number of near misses between Ted & the Mother meeting. Hell, the mere fact that the night before the wedding, they're both miserable & don't realise the love of their life is literally on the other side of a wall to them.

** Ted mourned her for ''six years'' (a full year longer than she mourned her first love, Max). Even though he knew it was okay to let her go he couldn't because he loved her so much.

* The BreakingTheFellowship that occurred in the finale. These 5 friends that we got to know and spent 9 years having fun together, and being nearly inseparable, just drift apart. It's a sad reality that many people have encountered in real life and is a harsh truth nobody wants to face, that life is unpredictable, everyone has a different path, and people do grow up and change. Nothing will ever be the same again.

** [[UpToEleven Even worse]], we learn that Marshall secretly fears the only reason Lily came back to him was because she failed in San Francisco, and when he asks her all Lily can do is run out of the room in tears.

* Marshall's breakdown outside of his father's funeral in ''Last Words''. Brings out all the emotions that run through a person in that circumstance.

** This becomes ''even more'' a tearjerker [[HarsherInHindsight in hindsight, since we eventually learn that The Mother won't live past 2024. [[SincerityMode Poor Ted]].]]

* Ted and Barney's fight about Chicago is just so utterly ''painful'' for both of them. Barney initially thinks Ted not telling him was because he didn't care, and we all know he has ''huge'' abandonment issues as it is and considering Ted wasn't going to tell Barney until he had to leave is understandable. But Ted ''does'' care, he just doesn't want to take away from the happiness of his two best friends getting married, even though though he's leaving ''[[LoveHurts because'' [[IWantMyBelovedToBeHappy they're getting married]]. True, Ted does steal the Glen [=McKenna=] to make up for it and Barney does accept his decision, but even then they still have to say goodbye to each other. The "I'm going to miss you" and the hug really did it.]]