Top 10 Most Embarrassing Things That Happened to Ted on HIMYM
#10: Mistakenly Assuming What His Date’s Job Is “Mary the Paralegal”
When Robin is angered at him for lying about breaking up with Victoria to hook up with her, Ted tries to get revenge by finding a beautiful date. This is set up by Barney, who claims the woman is a hooker posing as Mary the paralegal. While he has reservations dating a supposed prostitute, Ted finds himself enjoying her company. His limits are tested when Mary invites him over to her room, and Ted is forced to confront her. He then goes so far as to begin arguing with Mary that she’s a prostitute, despite her repeated claims that she’s not. Unfortunately, Ted’s too late to realize this, and an offended Mary kicks him out. To complete his embarrassment, Barney and Marshall waste no time laughing in Ted’s face.
#9: Teaching the Wrong Class “Definitions”
After realizing that being a teacher is his true calling, Ted begins his new job as a professor of architecture. However, things go wrong straight away, as a nervous Ted is unsure how to address his new students. Alternating between personas of a chill professor and an unreasonably stern one, he proceeds to speak in circles. Rather than charm his students as he hoped, Ted continues to make awkward conversation, including failed attempts at humor. After his nervousness gets the best of him, which involves even forgetting how to spell words, he’s horrified to learn that he’s been “teaching” Econ 305 all along. It's a small consolation that at least The Mother appreciated that shellfish joke.
#8: Witnessing Marshall & Lily's First Time “First Time in New York”
Ted, Lily, and Marshall have always been an exceptionally close trio. Despite realizing that he shared the same toothbrush with them for almost a decade, Ted was part of an even more embarrassing situation involving the couple. Having become best friends with Marshall as roommates in college, Ted also had to be around for Marshall’s more intimate moments. As shown in a flashback, Marshall and Lily get together for the first time in his dormitory room. While they present it as a romantic story, Ted reveals that his recollection of things aren’t all that memorable. To make matters worse, not only did Marshall and Lily ignore Ted, they evidently did it again despite his protests. Many years later, Ted finds himself at the wrong place once again.
#7: Telling His Date He’s Peeing Himself “Okay Awesome”
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When Robin sets Ted up with a friend at the cool new club known as Okay, he and Barney head over to find out it’s a bit too loud for comfort. Despite giving his date a chance, Ted begins to get annoyed when he realizes she’s more interested in dancing than listening. In order to get some fun out of this situation, he begins screaming random and outrageous statements. Ted’s luck runs out, however, as the music cuts away just when he delivers his craziest line yet. With the entire dance floor having heard about Ted’s supposedly unfortunate accident, and no hope to get his date back, Ted’s forced to concede that clubs just aren’t for him.
#6: The Pineapple Incident “The Pineapple Incident”
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Jealous of Robin’s new rich date, and dismayed with the lack of progress in his love life, Ted takes Barney’s advice to stop thinking. This leads to Ted becoming severely drunk, and he happily embarasses himself at McLaren's much to everyone’s amusement. The next day, a confused Ted pieces together the previous night’s events. Wondering who the mysterious girl he hooked up with is and why he’s woken up with a pineapple, he learns of his foolish behavior from his friends. This involves things like singing like a maniac, makes Carl the bartender think he’s hitting on him, and getting burned by Barney. Not only does he learn that Trudy, the girl in his bed, is ashamed of their hook-up; Ted also fails to remember why he has a pineapple in the first place.
#5: Getting a Lower Back Tattoo “Wait for It”
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The breakup with Robin hits Ted harder than he realizes. As his jealousy over her new handsome boyfriend Gael sets in, Ted decides to “win” the breakup by using Barney as his wingman. However, he takes an instant attraction to Amy, a tattooed girl who’s clearly bad news. Ignoring Barney’s arguments against Amy, Ted decides to go along with her crazy antics. After going a little too far in his over-the-top behavior, he finds himself about to get a tattoo. Unfortunately, Ted doesn’t remember this until the next morning, and upon learning this fact, his friends launch into a tirade of jokes. Realizing that he’s gotten a butterfly tattoo on his back, a horrified Ted’s humiliation is complete when Barney calls it this: [“it’s a tramp stamp.”]
#4: Partaking in Barney's Plays “Weekend at Barney’s”
At a time when his friends are in committed relationships, and being the only single one left, Ted agrees to take part in plays from Barney’s playbook. He ends up regretting this move, as Barney decides to make Ted go through the most outrageous moves imaginable. Despite some promising material, which makes it seem as if Ted might be successful, Barney’s insistence of using his horrible punch line gets Ted into trouble each time. Eventually, Ted’s constant bickering in his ear with Barney bugs him to the point where he begins to embarrass himself on his own. Poor Ted’s luckless day is sealed when his ex-girlfriend Jeanette finds the playbook and publicly destroys his possessions, even his beloved cowboy boots.
#3: Getting Beaten Up for Dumping His Girlfriend on Her Birthday “Return of the Shirt”
There are some embarrassments that are thoroughly deserved, and this is the one for Ted. Upon being overcome by nostalgia over his ex-girlfriend Natalie, he pursues her once again until she takes him back. In classic Ted Mosby fashion, though, he soon realizes he’s made a big mistake, and thinking he’s doing the noble thing, breaks up with Natalie. It’s too bad he picks the worst timing, as an incensed Natalie reminds him that he’s just broken up with her on her birthday. Having done the same thing on their last breakup, Ted’s excuses only make Natalie angrier. It’s here that Ted gets a painful lesson in Krav Maga, as Natalie delivers a beatdown that Future Ted's children find hilarious.
#2: Classic Schmosby Videos “The Best Man”
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It’s one thing to be publicly humiliated, and another to have others laugh at your misery. For Ted, this came true when his repeated mishaps in love made him an internet celebrity. At his childhood friend Punchy’s wedding, he learns that his school friends have filmed his many meltdowns over the years and put them up on the internet. These turn out to be so popular that fans show up from as far away as Finland just to meet Ted. Of course, there’s also the nickname that Ted is stuck with, as his classmates love to rib on “Schmosby” and the fact that most wedding guests actually turn up just to see him lose it again. Fortunately, Marshall sticks up to defend his friend. Before we unveil our top pick, here are a few honorable mentions. Getting His Hair Dyed Blonde, “Doppelgangers” Because This Is a Chance at Humiliation His Friends Can’t Pass on Getting Beaten Up by a Goat, “The Leap” Because Ted’s Fighting Skills Are Hilariously Awful Finding Out an Adult Star Uses His Name, “I’m Not That Guy” Because That’s the Not the Best Kind of Mix-Up Firing a Man While He Has a Heart Attack, “Columns” So Much for Being the Good Boss Has a Movie Made About Him Where He's the Villain, “The Wedding Bride” Because Millions Laughed at Ted’s Misery
#1: Saying "I Love You" on the First Date “Pilot”
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All of Ted’s failures in his relationships can probably be traced back to this moment. The second he lays eyes on Robin, Ted falls head over heels in love. And while their first date starts off , including him stealing the blue french horn for her, Ted ultimately messes up any future chances when they resume their date following an interruption. Just when things seem to be perfect, he says the three words you never say on the first date. Along with ruining things with Robin, Ted’s spontaneous confession of love becomes a recurring gag among the gang. Terming this as “the Mosby”, his friends not only make fun of Ted, but also use the move themselves when hoping to get rid of an unwanted lover.
