Top 10 Worst Dates on How I Met Your Mother

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Top 10 Worst Dates on How I Met Your Mother

VOICE OVER: Phoebe de Jeu WRITTEN BY: Garrett Alden
On the road to meeting the Mother, Ted and company had a lot of bad dates. For this list, we'll be going over the most embarrassing, painful, or just awkward dates characters on this sitcom went on. Our countdown includes Ten & Jen, Robin & Ian, Ted & Natalie, and more!
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Top 10 Worst Dates on HIMYM


Welcome to MsMojo and today we’ll be counting down our picks for the Top 10 Worst Dates on “How I Met Your Mother.”
For this list, we’ll be going over the most embarrassing, painful, or just awkward dates characters on this sitcom went on.

If there’s a date the MacLaren’s gang went on that was decidedly not awesome, please let us know in the comments!

#10: Ted & Blah Blah
“How I Met Everyone Else”


Sure, her real name is Carol, but Ted doesn’t remember that right away. Also, it’s funnier. A woman Ted met online while playing “World of Warcraft,” Blah Blah is definitely on the wrong part of the hot/crazy scale. Jealous and narcissistic, she spends the entire evening at MacLaren's comparing herself with Robin and stirring up drama. She practically threatens Ted with exposing his new info about how Lily and Marshall met. Blah Blah is easily a hallmark of why sometimes hot isn’t worth the crazy. Still, at least their date did give us some great flashbacks on how the gang met each other.

#9: Ted & Jen
“Double Date”


Sometimes you only realize how bad a date was with hindsight. When Ted and Jen go out on a blind date, they realize that they’ve been on the same date years ago. They decide to spend their second date deconstructing what went wrong the first time. Ted is snobby and oblivious, while Jen can’t stop talking about her cats and her ex-boyfriend. While they do share a nice moment on the roof, Ted never calls her again. Thankfully, their second date goes much better, as they both learn some things about themselves, even if they decide not to pursue a relationship.

#8: Robin & Ian
“Third Wheel”


Before going out on a date with Ian, Robin shares with her friends that she has decided not to shave her legs on the first few dates so as not to go too fast. However, she soon regrets this policy, after meeting Ian, who’s British, hot, and a doctor. She tries to get Lily to bring her a razor so she can shave in the bathroom. When that falls through, she bribes a waitress to get one for her. But a slip and fall in the bathroom leaves her barely conscious on the bathroom floor, the waitress stealing Ian away, and Robin out 50 bucks.

#7: Ted & Cassie
“Knight Vision” & “The Lighthouse”


At Robin and Barney’s wedding, Ted is offered his pick of women to try to pick up over the weekend. Unfortunately, according to a ghostly vision of the knight from “Indiana Jones and the Last Crusade,” he chooses… poorly. Cassie may be beautiful, but her life becomes an absolute train wreck during the wedding weekend. She loses her job, her ex is at the wedding, her uncle dies, and when they try to have sex, she cries and vomits. Their trip up a lighthouse also results in her breaking her ankle and Ted vomiting off of it. The only silver lining is that Ted not getting together with anyone during the wedding means that he met his future wife by the end of it.

#6: Ted & Amy
“Wait For It”


After his breakup with Robin, the first breakup anyway, Ted goes on the rebound – in a big way! Determined to win the breakup, Ted hooks up with Amy at the bar. Amy is wild and has little respect for things like the law, stealing from the bar, and taking Ted and Barney to a hot tub at a house that was supposed to be empty but was not. To put it in perspective, Barney is the voice of reason on their double date with her friend. BARNEY! The night ends with her taking Ted to get a tattoo, unfortunately at her ex-boyfriend’s parlor. Ted’s infamous butterfly tramp stamp may have been worth it, though.

#5: Marshall / Lily & Robin / Barney
“The Sexless Innkeeper”


Marshall and Lily are grade-A adorable, but even they have their faults. One of them is that they’re desperate to have more couple friends. So when Robin and Barney get together, they decide to have a double date. They come on… a little strong. Both of them are nervous about the evening going well and every setback has them panicking. And then there’s Marshall’s website with a video montage entitled “It was the best night ever.” The song is catchy and entertaining, but it’s clear from the pictures that Robin and Barney are not having a good time. Thankfully, the foursome manages to patch things up.

#4: Ted & Natalie
“Return of the Shirt”


Some of these dates feature things going wrong because of the person one of the gang dates. This one is entirely on Ted. Ted decides to give an old girlfriend another try and wins back Natalie, whom he tragically broke up with on her birthday over the phone. Even more tragically, he decides to break up with her again 3 weeks later, when he feels like she isn’t “the one” – again on her birthday! With just a little more awareness, Ted could have avoided the ensuing beatdown she gave him in a restaurant. Krav Maga is no joke!

#3: Barney & Quinn
“Karma”


For the record, we’re not talking Barney and Quinn’s full relationship – they were surprisingly good together (until they suddenly weren’t). No, instead we’re looking towards the beginning of their acquaintance. After realizing she’s a stripper, Barney tries to win Quinn over. Because this happens where she works, Quinn insists on Barney paying her for a dance to make it “seem” like she’s working to her boss. This date ends up being Quinn essentially manipulating Barney into giving her money, which is not the best foundation for a relationship, it has to be said.

#2: Barney Tries the Naked Man
“The Naked Man”


When Robin has a date with Mitch, Ted walks in on him performing “the naked man.” Just as it implies, he waits while naked, which, according to him, leads to sex… two out of three times. When the rest of the gang hears about it, they all decide to try it out. Lily tries it on Marshall, which works, and Ted is successful with his date as well. Barney, who believes the Naked Man will revolutionize dating, is the unfortunate 1 out of 3 times when it doesn’t work. His date kicks him out of her place stark naked, forcing him to wander the streets in the buff. It could be worse though – if his rejection of free cheap suits is any indication.

#1: Ted & Robin
“Pilot” & “Game Night”


Take it easy, Ted and Robin fans – hear us out! Although Ted and Robin do hit it off, and they do get together eventually (multiple times), there’s no arguing that their first date is full of missteps. While they share common interests and things seem to be going well, their trip up to Robin’s place is interrupted when she’s called away for a story. Then, when Ted goes as far as to go back later after stealing the blue French horn, in a romantic gesture, he biffs it by telling her he loves her way too quickly! He even misses “the signal.” Oh, and his re-return after getting drunk and throwing up on her doormat didn’t help either.
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