How I Met Your Mother 10 Worst First Dates The Characters Had

How I Met Your Mother: 10 Worst First Dates The Characters Had

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Ted, Robin, and Barney may have found their perfect match in the end but they did have to go through some awful dates to get there.

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How I Met Your Mother 10 Worst First Dates The Characters Had

Love is one of the major themes of How I Met Your Mother. After all, it’s a show all about how Ted met the woman of his dreams and mother to his children, Tracy. Of course, the dating process usually requires a first date of sorts.

For Ted and Tracy, their first date didn’t go quite as planned but it was adorable and ultimately successful. However, the same can’t be said for many of Ted’s other first dates or those involving the other characters on the show. As all of the members of the gang went on a journey to find love, they occasionally had some awful romantic encounters on the way, with some of them ending before they even started.

10 Robin And Ian

How I Met Your Mother 10 Worst First Dates The Characters Had

In an effort to “behave” herself, Robin decides that for her first date with Ian, she wouldn’t shave her legs until at least three dates. Turns out, Ian is a charming and attractive British brain surgeon who Robin realizes she won’t be able to resist by the end of the night.

Breaking her no shave rule, Robin tries her hardest to shave her legs quickly, going as far as paying the waitress $50 to get her a razor. Her attempts at a last-minute leg shave doesn’t go over so well in this public bathroom. By the end of the night, she’s stuck in the bathroom, giving the annoyed waitress time to swoop in and take Ian.

9 Ted With Robyn, Lizbeth, And Holly

How I Met Your Mother 10 Worst First Dates The Characters Had

It’s tough to get over a break-up. All it takes is one little thing to remind a person of them and all of those painful memories come flooding back. For Ted, however, just about everything reminded him of Robin.

In order to get past his recent heartbreak with Robin, Ted is set up with three girls. The problem is, Ted sees similarities to Robin in all three of them. Robyn, of course, is an obvious stand out because of her name. With Lizbeth, all it took was her to say “lasagna” to remind Ted of that very one time Robin made it (poorly). Then there’s Holly, whose ex-husband’s name is Wayne, forcing Ted to connect it to Batman, whose sidekick’s name is Robin.

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8 Ted And Janet McIntyre

How I Met Your Mother 10 Worst First Dates The Characters Had

Nowadays, it’s so easy to look someone up on social media before you even meet them. Annoyed by this trend, Ted and Janet make a promise to not look each other up online before their first date.

Unfortunately, Barney and Robin are too impatient and they decide to look her up, against Ted’s wishes. They find out that Janet is basically a perfect person who saves lives and has a billion-dollar fortune. If only they hadn’t insisted Ted look up the info they found, Ted may have had a good future with Janet. Instead, curiosity got the better of him and he became too self-conscious to even speak to her even further.

7 Barney And His Magic Phone

How I Met Your Mother 10 Worst First Dates The Characters Had

In one of Barney’s most extreme attempts at getting women, he literally shows his phone number to millions of viewers during the Super Bowl. This turns out to be successful, maybe a little too successful.

Barney’s phone just doesn’t stop ringing. Every time he does meet one of the girls, he’s immediately distracted by the texts and calls he’s getting from other women. The fear of missing out on a potentially hotter girl gets to be too much. By the end of the night, Barney realizes that the magic phone he possesses is actually a curse.

6 Ted And Jen

How I Met Your Mother 10 Worst First Dates The Characters Had

Ted thinks he’s going on a blind date he was set up with. Little does he know, he had met this exact same woman years earlier on another blind date. After realizing this, they both reminisce on what made their original date so bad.

Both of them were at fault for making the date a failure, from Ted pointing typos in the menu to Jen not doing “the cheque dance.” Let’s also not forget that Ted was in his infamous goatee phase that almost everyone agrees is not a good look for him. Of course, people do grow and change. It’s just a shame that they weren’t destined to be together despite getting another chance.

5 Marshall/Lily And Robin/Barney

How I Met Your Mother 10 Worst First Dates The Characters Had

Marshall and Lily have always wanted a couple they could hang out with, something that was difficult when you hang out with all single people. Once Robin and Barney started dating, Lily and Marshall couldn’t wait to have their first couples’ night with them. It was essentially the first date as far Lily and Marshall were concerned.

For Marshall and Lily, it was the best night ever. However, for Barney and Robin, it was one of the worst nights ever. Marshall and Lily try way too hard to make the night perfect, coming off a little desperate. Marshall also takes a little too much pride in his gouda slices, the only thing Lily would allow him to prepare.

4 Barney’s Naked Man Attempt

How I Met Your Mother 10 Worst First Dates The Characters Had

Two out of three times. That’s the success rate of The Naked Man, as invented by Mitch. After Mitch got it to work with Robin, Ted and Barney both agree to try The Naked Man on some first dates. Lily also gives an attempt on Marshall that same night.

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As statistics would show, The Naked Man worked two times that night (obviously it was going to work for Lily). The odd one out was Barney, who’s attempt ended poorly, to say the least. The unnamed woman was so horrified that she threatened to call the police and kicked out a still nude Barney. Barney was forced to walk around New York City completely naked, yet still refused to put on a cheap suit that he found.

3 Ted And Cindy

How I Met Your Mother 10 Worst First Dates The Characters Had

Ted’s first date with Cindy actually goes kind of well. It’s only in retrospect that it must be an awkward time. It’s revealed that Cindy’s roommate was Tracy, the woman Ted would end up marrying and begin telling his kids a nine-year-long story of how he met her.

The entire date, a self-conscious Cindy kept going on and on about a little these quirks she couldn’t stand about Tracy. Ted had to sit there and pretend that Tracy is just so lame. In reality, he thought she sounded awesome. This would later ruin his relationship with Cindy as he points objects in her room that he thinks are cool, all of which actually belonged to Tracy.

2 Ted And Amy

How I Met Your Mother 10 Worst First Dates The Characters Had

After Robin brings home her new boyfriend, Gael, Ted makes it his mission to come out on top and win the break-up. His solution is the wild and unpredictable Amy, who takes him out on a drunken night where Ted ends up blacking out at a tattoo parlor.

Thinking he avoided getting a tattoo, Ted thought the whole night was a win. Unbeknownst to him, the tattoo artist was Amy’s ex-boyfriend, takes his jealousy out on Ted’s lower back, giving him a butterfly tattoo. In a way, this tattoo turned out to be a blessing and a curse since it led him to meet Stella. Stella may have left him at the altar but is also responsible for getting Ted his job as a professor.

1 Ted And Robin

To say Ted and Robin had a rocky relationship would be an understatement. They were together for a while before breaking up. Then, they became the best of friends but had some heartbreaks along the way. In the end, however, they would find their way back to each other.

All of this started with their hilariously awkward first date. The actual night had been perfect until the last second, where Ted made things weird. Being the hopeless romantic that he is, Ted confesses his love for Robin. This might just be one of Ted’s most embarrassing moments of the show that the gang will never let him forget.

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