most emotional episodes of how i met your mother

I have Googled “most emotional episodes of how I met your mother” so often for so many years that it has spawned a playlist:

and an emotional disaster indicator level:

and I’ve never found a satisfactory compilation. I HAVE TO DO EVERYTHING AROUND HERE!

This list is my opinion and is free from boring dynamic alpha emotions such as “marshall sad dad died” and “ted angry robin kiss new man.” Instead it clings so amorously to bittersweetness and faith-infused uncertainty that it could kiss them on the mouth. 

Enjoy, children, everything (this listicle) I didn’t have growing up.

*I’ve realized I’ve written exclusively about bittersweet monologues, which is the cheating-at-charades-by-speaking-in-synonyms version of “emotional episodes.” Below find the most bittersweet monologues of How I Met Your Mother. 

You watch this episode for the final scene, where Klaus tells Ted about the German* (*fake?) concepts of Lebenslangerschicksalsschatz and Beinaheleidenschaftsgegenstand, the former meaning “lifelong treasure of destiny” and the latter, “almost the thing that you want, but not quite.” Delightful guest Thomas Lennon as Klaus comes in and absolutely bodies the marriage of twee comic stylings and fatherly sentimental gravitas that characterize HIMYM. His delivery lends the above definitions the same mouthfeel of a heartstring-pulling Shins outro song. Luckily we mix it up and get Band of Horses’ “The Funeral” playing as Ted announces it would be a while until he meets his Lebenslangerschicksalsschatz, but as for the where: “a ways down the road” The Mother, under cover of yellow umbrella, walks up next to Ted at the same train stop in Farhampton (just Googled, not a real place, not cool guys, I am but a humble Georgian who doesn’t know which of your fucking hamptons are real and not real) where Klaus gave his oration. While Klaus’ idea that Lebenslangerschicksalsschatz is “instantaneous” feels ambitious, his insistence that “everyone (feels it) eventually. You just never know when, or where” embodies the show’s essential ethos..es on the unknowability but destiny of the universe, and inflates the outlook with a gust of faith.

This episode lodged itself into my consciousness so much I referenced it in therapy one hour ago and always call it by its full government name, see above. You watch this episode for Lily’s “Mistakes” monologue, which she delivers - nay, barrels through - when Ted tells her that seeking out an art internship across the country that would conflict with her and Marshall’s wedding is “a mistake.” 

“Okay, yes, it's a mistake.

I know it's a mistake.

But there are certain things in life where you know it's a mistake, but you don't really know it's a mistake, because the only way to really know it's a mistake is to make the mistake, and look back, and say, ‘Yep. That was a mistake.’ So, really, the bigger mistake would be to not make the mistake, because then you go your whole life not really knowing if something is a mistake or not. 

And, damn it, I've made no mistakes! I've done all of this-- my life, my relationship, my career-- mistake-free. Does any of this make sense to you?”

In college I used to go into empty lecture halls and watch this monologue alone on the projectors. It is such a watershed moment in my brain, and the pounding heart of the episode, that it wasn’t until recently that I realized there are TWO world-historical HIMYM moments here, bully for us!!

Not so in later entries, the B and C plots synchronize beautifully with the mistake theme of the A-plot; earlier in the episode, Lily insists on touching a hot plate, Ted knowingly chugs from a jug of spoiled milk, and Robin gets bad highlights she says are giving Tony the Tiger but I say are giving Bratz and thus cunt(z). Reflecting on those mistakes, voiceover Ted admits that Lily’s right, sometimes you gotta make the mistake — and skips a date at McLaren’s with his algorithmically-determined perfect match to chase Robin. His moment of realization comes after she’s dropped him off at the bar, and he’s frozen outside the door, struck by a vision of his future wedding with Robin… in the front row. He’s fixated on her angelic face there, and “Mother of Pearl” by Roxy Music swings in (“Mother of Pearl, I wouldn’t trade you for another girl”), in one of the most affecting needle drops of this or perhaps any show. 

The “Mistakes” monologue and “Mother of Pearl” were singlehandedly responsible for romantic mistakes decisions of mine in 2019 and 2022, respectively. Once again count your backslide blessings, and watch this episode if you need some spiritual backup on a risk. 

Late season 4 is getting into suboptimal territory. You sorta skip most of this episode, and cut to Ted and Stella’s kiki in her car, where he sighs into the exasperation of a Romantic beaten and deprived (the dark I know well…). “What you and Tony have, what I thought, for a second, what you and I had, what I know that Marshall and Lily have: I want that. I do. I keep waiting for it to happen and waiting for it to happen and, I guess I’m just. I’m tired of waiting.” 

Ugh. Fuck. Ow. OW! Ted is speaking for the trees (girls who have been recovering from their breakup for 15 months and are ready to find a wife to lay on the couch and ultimately move to Asheville, North Carolina with). I’ve recently said that my getting laid is a matter of public health importance, and my volcel brother here seems to be in the same canoe. Now let’s go to Stella for a traffic update. Stella? 

“You know, I once talked my way out of a speeding ticket. I was heading upstate to my parents’ house doing like ninety on this country road and I got pulled over. So this cop gets out of his car, he kind of swaggers over, and goes, ‘Young lady, I have been waitin’ for you all day.’ So I looked up at him and I said ‘I’m so sorry officer, I got here as fast as I could!’” Stella is a LIAR and this never actually happened to her, but: “I know that you’re tired of waiting, and you may have to wait a little while more, but she’s on her way, Ted, and she’s getting here as fast as she can.” 

This show has a big ole crush on time and waiting and this is a great example: time, here, inspires loneliness, deprivation, hopelessness, frustration, loss of identity — but also hope, faith, belief in a system of destiny and its goodwill toward us. In the same way if Glee were around today Will and Artie would have done “Nice For What,” if HIMYM were made now, as Ted stands on the curb with yellow umbrella in hand, “invisible string” (LONG POND VERSION ALWAYS) would close the ep. And it would rock. 

Two things happen in this episode, One, Robin and Barney do their awesome choreographed dance to “Groove is in the Heart.” It is the single best, nay, only good, moment of their relationship. 

Two, Ted and Robin have a Canada Kiki (smoking cigars outside) and in classic Cancer-Sagittarius Pairing fashion, Ted asks if Robin is OK, Robin says no, Ted isn’t either, Ted asks if Robin wants to talk about it, Robin super does not, Ted says it might make her feel better (nosy), and Robin tells Ted to go first and that she will stick with her thing about not talking about it. Ted, a la his chat with Stella but three years later (F) has lost hope. All his high school friends are at the wedding with their wives and babies. He now thinks the women reading in line at the bagel shop are bitches. (the volcel has curdled into an incel) 

Ted no longer believes in destiny (Cancer), which Robin scoffs at; what really matters is chemistry (Sag). “If you have chemistry, you only need one other thing. Timing. But timing’s a bitch.” 

This is, obviously, not even a little bit true. (Sag delusion) Relationships are built on ninety thousand levels of matching dispositions, coincidences, circumstances, and television preferences.

However, this folk axiom is very comforting when your entanglement went awry and you’re still convinced it was meant to be and now it isn’t. Then, your friends can remind you that timing’s a bitch, and you can be genuinely comforted by that true piece of Robin’s completely unrealistic romantic schema. 

For my Pop Culture Warehouse-brained integrity I have to talk about this episode and I really don’t want to because it makes me so severely emotional. I am going to go get some pie from the shop downstairs and come back. 

OK. So. 

In this episode we follow Tracy Thee Mommy’s life starting the night we started following Ted back in 2005, which happens to be her 21st birthday. The thing is that on this day, the love of Tracy’s life dies. For the next decade she shuts herself away and works her little chastity belt off donating instruments and going to economics school to figure out how to fix poverty. She rebuffs suitors by telling them she is sixteen (OK Christy Hansen!) or that true love is like a lottery ticket, and the first ticket she bought was a winner, but then the ticket died, so that is pretty much curtains for her. 

She eventually starts dating this boring guy who tolerates but does not know how to respond to her renditions of showtunes performed by breakfast food. (This is real; it is so lonely for someone to be like “cute!” about your fun intense parts and not know how to engage with them. I am being serious about Tracy Thee Mommy’s breakfast incompatibility) In fake ass Farhampton, at Robin and Barney’s wedding, this J Crew native advertisement asks Mommy to marry him, and she looks like a deer that has been proposed to by someone it does not want to marry. She flees to the rental house porch, wraps herself around a pillar, and locks eyes with the night sky to ask her dead lover if this is OK. 

I am going to self-immolate.

At this point in the episode, if someone in your life has died, you are crying. If you cannot move on from a past love, you are crying. A third experience, I guess. I have only ever had the two. 

She secures approval and a dowry from Ex In The Sky, goes inside, and - TWIST - rejects Quarter-Zip. This show’s final season stands on the carcasses of dozens of broken and rejected engagements. Trac-E concludes her fifteen minutes in the spotlight by checking into the Farhampton hotel and settling into the balcony to play a rendition of La Vie En Rose absolutely full to bursting, 3-weeks-past-due-and-ready-to-pop, falling-off-the-vine-ripe with wistful tenderness, on a ukulele I am just now realizing is one her Late King gave her at the top of the episode. Fuck.

It is the first time Ted, on the adjoining balcony, hears her voice. 

Fucking Christ. Jesus fuck, dude. Oh my god. 

This show consistently presents past lovers as an existential threat or maddening impediment to new love. (hetero monogamous jealous hater shit) In this episode, though, the cinematic narrator softens for Tracy, lovingly conceding that past loves need not be monsters under beds or demons to disavow. Ted’s been fumbling for destiny in a hazy vision of the future, but for Tracy, her life has long been defined by a clear destiny; to have loved that man, to have lost him, and to go on loving him. The past is destiny as much as the future, and we carry some loves with us like a little immortal torch as we trek forward alone. 

Tracy, and this ideology, obviously model the series finale and the ideology of the show it elucidates. More on that below!

I’m writing thousands of words about one scene in this episode, so no spoilers. c u there. 

• When Ted finds Victoria in S1E13 and runs into her bakery as “Spit on a Stranger” by Pavement plays. Points deducted because Spit on a Stranger is a hopeful post-breakup song, not a falling in love song. Spit on a Stranger is single people’s business.

• When Ted and Robin break up in S2E22 “Something Blue” because Robin “doesn’t want kids in Argentina” and Ted “doesn’t want kids in Argentina.” Bonus points for supporting my point that Ted and Robin are the quintessential first-edition mint-condition Cancer-Sagittarius fated and doomed pairing. Points off because there’s very little “bitter” here. Ted is sort of like, “if you know what you want from life, life gives it to you. Robin wanted a globetrotting career, I wanted a scotch. It all worked out.” Like, I guess?

• When Ted and Lily do Confession Time on the roof and Ted says Robin shouldn’t be with Barney, she should be with him; and Lily says sometimes she wishes she wasn’t a mom. Points off because this level of emotional honesty is typical of a regular Friday in my friend group.

• The one where grown Ted imagines running to the mother’s door to tell her they’ll meet soon but he wants her now, wants every second with her. Points off because I am writing about it in the other thing I talked about earlier, and also because I lied when I said I left to get pie and the place is closing soon.