Harsher In Hindsight / How I Met Your Mother

• Immediately before his first date with Stella, Ted acknowledges—for probability's sake—that the relationship will probably end on a bad note. He also states that if their relationship does end, it won't be because of some stupid rule. Stella leaves Ted at the altar because he broke the rule about not bringing exes to your wedding.
• Several times during the first few seasons, Robin talks about she doesn't want kids. It's even the biggest reason she and Ted broke up. In season seven, she learns she can't have kids. This is especially harder to watch around 2015 when Cobie Smulders revealed that she was secretly battling ovarian cancer at the time the third season was being produced and was told there was a possibility that she couldn't have children. She became cancer free after two years of surgery and had two children (making this double as Heartwarming in Hindsight).
• Scooter, Lily's ex-boyfriend, is shown as still hopelessly in love with her. A season 8 episode reveals that she essentially forced him into being her boyfriend (out of sheer terror), and him being a Hopeless Suitor/Stalker with a Crush is almost a form of Stockholm Syndrome.
• Marshall feeling neglected by Lily while she's doing her job as an art consultant gets much harsher when it's revealed that he fears that he (and their life together) is nothing more than a "consolation prize" to her after failing as an artist. Which, you know, who knows whether she would have ever come back to him if she hadn't crashed so hard? This could be even harsher if one considers what Lily says on the rooftop in "Band or DJ?". Sometimes, she wishes she wasn't a mom. Sometimes she wishes to pack a bag and leave in the middle of the night and never look back. And even though she loves her family and Marvin, she regrets not being able to do more with her career. She has never talked to Marshall about this. It makes his fears seem even more justified.
• In "The Perfect Week," Barney is secretly fretting that he might lose his job. "Unpause" finally shows us his job which is being the fall guy for GNB's illegal activities. As such he wasn't just risking losing his job, but probably going to jail for a very long time.
• Ted's anger at Barney in the final episodes of the third season due to Barney's sleeping with Robin becomes incredibly hypocritical when you realize that Ted spends a large chunk of the last half of season 8 and the majority of season 9 hoping that Robin would realize she loves Ted instead of Barney and call off their wedding; and that when Ted starts pursuing Robin again in the final moments of the series, he's doing the exact same thing that Barney did to (temporarily) ruin their friendship—dating his best friend's ex.
• In "Not a Father's Day", Ted tells Robin it's a good thing she's not a mother because she is such a cold person. Pretty harsh when you find out that she can't have kids.
• Post-finale, a moment in "Shelter Island" becomes this. When Ted imagines how life would be different if he'd married Stella, the daydream includes having a wife who's still alive.
• In season 5, during a flashback, Lily wants to take a group shot of the gang to commemorate Robin's naturalization in her scrapbook, but she doesn't want Robin and Barney—who were dating at the time—to sit next to each other and look couple-y. She exclaims, "Of course I don't [want you and Barney to look like a couple in this picture]! You two aren't going to last. I'm going for timeless here," a sentiment that Robin and Barney agree with. It's not as harsh when they break up the first time, but it is very harsh when in the series finale it is revealed that after three years of marriage, they decided to divorce.
• In a bittersweet way the ending of "The Time Travelers" becomes this in light of the finale. Ted says that if he could go back to that time he would met the mother 45 days earlier. Upon first viewing it just seems like he's romantically wishing he could have started their life together as soon as possible. After the finale, you realize they actually had far less time together than he ever would have expected and the chance to have 45 days more would have meant a lot.
• The entirety of "Vesuvius" takes on a bittersweet quality in light of the finale. Various references in the episode are explained when you realize the mother had died and it's clear that they already knew she was dying on that trip, even talking about how when things get too intense it's sometimes best to leave them unspoken and just enjoy each other's company. In particular, Ted gets very upset at the end at the thought of a mother not being around for her own daughter's wedding.
• The majority of the last two seasons can be this to some fans, considering how much time is devoted to showcasing how Robin and Barney make a great couple.
• A season 1 episode has Barney courting a bridesmaid, his excuse for never seeing her again being that in the morning he's shipping out with the Peace Corps for two years. We find out mere episodes later that his Start of Darkness was getting stood up by his girlfriend the day they were supposed to ship out with the Peace Corps together for two years.
• In an early episode, Robin off-handedly jokes that she doesn't want kids, but might when she's like 60 or so. She insists that "medicine will catch up." Cue revelation that she cannot have children at all.
• In "Double Date" Marshall explains how a husband like him fantasizes about other women than Lily: First he has to kill Lily off via Soap Opera Disease, then lets "an appropriate amount of years" slip until said other woman reappears in his life and they can get it on. Of course everybody around Marshall agrees that this is ridiculous, disturbing, sad etc. And it bears an uncanny resemblance to what the writers eventually do to Tracy/The Mother in order to have Ted end up with Robin, though the mother's death is shown even more in passing than Lily's in the fantasy. What's really disturbing is that given the fact that the kids' final scene of "Lol, Mom's been dead for six years, go plough Aunt Robin like a cornfield" had already been filmed, this fantasy was probably completely intended to be Foreshadowing.
• Ted's kids, asking "Are we being punished or something?" and rolling their eyes at the beginning of the story looks pretty darn callous knowing that their wonderful, saintly mother is actually dead.
• In "The Yips," one of the plots involves the group joining a gym and Marshall (and later Ted) falling prey to a hardass gym trainer, who yells at Marshall that if he doesn't try harder she'll just leave him to the massive coronary that's coming his way. Nothing more than a throwaway joke until three seasons later, when Marshall's dad dies of a heart attack, implied to be a result of his diet and exercise habits.
• Hammond Druthers goes through a serious Humiliation Conga in his birthday in a Season 2 episode. His most famous character, Walter White similarly goes through a Humiliation Conga in all his birthdays, starting from getting a cancer diagnosis in his 50th birthday and desperately turning to cooking meth to his death in his 52nd birthday.
• In one episode, Lily teases Ted for wearing sweaters similar to the ones Bill Cosby was known for wearing. Ted responds, "Laugh all you want, America loved that man for a reason". With Cosby having faced numerous allegations of rape and sexual assault dating back to 1965, Ted has a lot less reasons to be proud of dressing like him.
• The episode "The Naked Man" revolves around a move in which a guy strips down while their date is out of the room in the hopes that they will be charmed enough to have sex with them. This episode looks a lot more disturbing in light of the Harvey Weinstein charges. Especially since Mitch (Robin's date and the first guy seen using this move) bears a passing resemblance to Weinstein, being a balding, paunchy man.
• Crossed with Fridge Logic; "We're Not From Here" has a plot in which Marshall and Lily write letters to each other for their "death folder". In the final moment of that episode, viewers are led to believe that after twenty years, Lily died and Marshall is about to read her letter, but she didn't in fact die, and she's mad at Marshall for opening her letter early yet again, which is basically "Busted! I knew you'd do it, you suck, Marshall, you totally suck". This is made hard to watch following the reveal at the end of the series that Ted lost the love of his life and mother of his children, to the point of raising the question of how does older Ted find this funny, since this can't be Hand Waved by the Framing Device as the voiceover has Ted specifically set the scene up for the children.
• In "Ted Moseby, Architect," the characters visit a Columbia University college party Marshall was invited to, with a number of jokes that these future lawyers, politicians and otherwise public figures had a history of of getting raging drunk. (girl spitting out alcohol) Future!Ted: "That is our attorney general." (shirtless guy asking people to shave his ass) "That guy went on to become a supreme court justice." The host also has the guests sign a waiver so the host won't be held accountable for any harm caused at the party. In September 2018, a nominee for the Supreme Court, Brett Kavanaugh, was accused of sexual assault while in high school and college, and a lot of the conversation when the subsequent hearings focused on that period of his life went to his partying days and him freely admitting to drinking a lot.
• Marshall's joke in Season 4 about there not being any black people in Minnesota is harsher after the death of George Floyd in Minneapolis in 2020 and the protests that occurred as a result.
• Barney's "Not a Father's Day" holiday from the season 4 episode of the same name becomes a bit darker as the "incel" (involuntarily celibate) movement gathered steam, with the line that these guys aren't childless by choice and paints them as, well, involuntarily celibate. While the movement existed before this episode, it wouldn't pick up steam and become a terrorism threat until into the 2010s.
• In "Cupcake", Barney's tailor speaks Russian, which Barney and Marshall identify as Ukrainian. Since 2014, Russia has been conducting a hybrid war in Ukraine, which culminated in a full-scale war in 2022, justifying their actions, among other things, as "protecting the Russian-speaking population". A lot of Ukrainians reacted to this excuse by switching from speaking Russian or both to using Ukrainian exclusively, and confusing one language for another went from a faux pas to being completely unacceptable.
• "Garbage Island" opens with Ted at the Hong Kong International Airport in 2021. While the writers' prediction of phones being able to project holograms is hilariously inaccurate, the idea of a crowded, maskless airport in 2021? Not so hilarious.
• The fact that Future Ted is voiced by Bob Saget while narrating the events from 2030. Saget passed away on January 9, 2022.

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