10 Couples That Hurt How I Met Your Mother (And 10 That Saved It)

How I Met Your Mother The Mother

One of the most successful modern sitcoms, How I Met Your Mother managed to pull off a truly impressive feat. It was popular enough to receive huge ratings while also attracting the kind of following that is more common for smaller, cult shows. Over the years, the series’ biggest fans even bought several books based on things like Barney’s Bro Code and his infamous Playbook.

While there is no doubt that the friendships shared among the core 5 How I Met Your Mother characters were hugely important, the show was still largely based around romantic couplings. After all, the series was all about a man’s endless search for the love of his life. However, some of the romantic pairings introduced over the show’s runs actually took away from fans' love for the series. It's time to look back on the best and the worst of the bunch.

In order for a couple from How I Met Your Mother to be considered for possible inclusion on this list, they first and foremost need to have been important enough to have impacted the show’s legacy. From there they were categorized into relationships that made the show a great deal better and those that took away from its quality. Finally, it should be noted that even How I Met Your Mother couples that were only briefly together were in the running, as long as they were important to the show’s fans in one way or another.

Here are 10 Couples That Hurt How I Met Your Mother (And 10 That Saved It).

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20 Hurt: Robin and Don

How I Met Your Mother Don

Introduced during How I Met Your Mother’s 5th season, Don Frank was hired as the new co-host of Robin’s show and right from the start there was some chemistry between them. An off-and-on couple throughout that season, it, at one point, seemed like they could wind up being a pretty serious pairing, at least in the short term. In fact, Robin even chose to turn down a news anchor job in Chicago in order to remain with Don-- unbeknownst to him. Unfortunately, she would be hugely disappointed to learn he was leaving because he was offered the same job and took it.

It was frustrating to invest in a relationship that went nowhere, and was ultimately revealed to be more of a plot device than anything else,

19 Saved: Ted and Cathy

Ted and Cathy were never meant to be, as it was only a matter of time before he realized that she never stopped talking. However, when the gang pointed it out to him and he heard glass shatter as his perception of her was burst, it was pretty hilarious. More than that, his irritation that his friends had ruined the way he saw Cathy led to a hilarious episode full of each of the core cast member’s foibles coming to light.

As means to an end, this couple was not especially meaningful, but the episode Cathy inspired is one of the best in series history, so they undoubtedly helped the show.

18 Hurt: Zoey and The Captain

How I Met Your Mother Zoey

The only couple on this list that does not involve one of the show’s core cast members, Zoey and The Captain were an odd pair who were pretty difficult to understand. The idea of Zoey marrying someone as obviously eccentric as The Captain seemed more than a little bit farfetched.

Right from the start, it seemed incredibly obvious that the only reason they were together was so there would be an obstacle in Ted’s attempts to wop Zoey. As a result, this pairing is yet another couple in the long history of gimmicky television relationships that only serve to draw out a storyline for as long as possible.

17 Saved: Robin and Simon

How I Met Your Mother Simon

James Van Der Beek is an underrated comedic actor; any Don’t Trust the B in Apartment 23 viewer would agree. The character he played on How I Met Your Mother, Simon Tremblay, was absolutely hilarious. As the first boyfriend Robin ever had, even as an adult, he still held enough sway over her that she failed to see his obviously negative qualities.

A balding and failed musician who still lives with his mother, Simon was also a self-centered jerk who broke up with Robin after she carried his gear to his van twice. While there were ample reasons to dislike him, this relationship was fun since it was never anything more than a joke with a funny punchline.

16 Hurt: Ted and Naomi

Josh Radnor as Ted Mosby and Katie Holmes as The Slutty Pumpkin on How I Met Your Mother

The woman in the Halloween pumpkin costume was given quite the introduction on How I Met Your Mother. Ted met her at a rooftop party and felt an instant connection, but he totally bungled things by losing her number and any chance to be with her.

Still, this is the romance-obsessed Ted we are talking about, so he returned to the same party wearing the same costume over and over again in hopes that she would arrive and recognize him. They were eventually able to reconnect several seasons after the character was first discussed, but after years of build-up they found they had shared zero chemistry. It was yet another "Mother" fake-out.

15 Saved: Robin and Kevin

How I Met Your Mother Kal Penn

By season 7, when Robin got involved with Kevin, her court-appointed therapist, fans realized he was unlikely to matter in the longterm. This was confirmed when she betrayed with Barney. Even when she agreed to marry Kevin, it was completely obvious that was not destined to happen.

Instead, viewers got to sit back and enjoy a wholly new element that Kevin’s character brought to the show: his mental health training. Kevin was the perfect person to address some of the deep-seated issues the gang dealt with, and his reactions to their antics were fun to see. On top of that, it was pretty hilarious to learn in season 9 that Kevin had become romantically involved with Jeanette.

14 Hurt: Lily and Scooter

How I Met Your Mother Scooter

As her love for Marshall was clear from the pilot, Lily Aldrin was only ever involved with two men, and one of those relationships was pretty awful. They were together during Lily’s goth phase, and it is abundantly clear that Lily  outgrew her first boyfriend Scooter when she outgrew that look.

On the other end of things, no matter how many years passed by Scooter never got over her and at first blush that made him seem like a pretty crazy dude. However, it turns out that ever since they broke up, Lily kept giving him reasons to hold out hope, which was pretty low of her, even if Marshall ended up helping to keep him on the hook.

13 Saved: Barney and Quinn

How I Met Your Mother Barney and Quinn

The perception of Barney as a relationship-adverse sociopath who heartlessly deceives women is certainly accurate at times.. However, over the seasons, the show revealed what inspired him to be so awful to his fellow human beings. More than that, he also grew as a person and ended up getting involved in a trio of serious relationships, including one with Quinn, his ex-fiancée.

Not only an independent woman who is able to hold her own with Barney, Quinn was also such a strong person that she made him want to become a better man and partner. Though they didn't last, if that isn’t the definition of a good relationship, we don’t know what is.

12 Hurt: Ted and Stella

How I Met Your Mother Sarah Chalke

From the moment Ted met Stella, the doctor he went to in order to have his ill-advised tattoo removed, he wanted to be with her. Nearing his final tattoo removal session and well aware that he may never see Stella again, Ted wouldn't give up-- despite the fact that she had made it clear that she didn’t want to date.

Though he was eventually able to wear her down, Ted should have listened when Stella made it clear she was not ready to be with him. Yet, somehow the show makes it seem like we are supposed to feel bad for Ted when Stella ends up getting back together with her ex. While Stella certainly should have turned down Ted’s proposal and timed their breakup better, based on how this relationship began, we never felt too bad for him.

11 Saved: Ted and Victoria (The first time)

How I Met Your Mother Ted and Victoria

The kind of introduction that often leads to long-lasting and loving relationships on television, when Ted and Victoria saw each other from across a room it seemed like love at first sight. Upping the ante further in terms of romantic comedy tropes, Victoria even convinced Ted to keep their real names a secret so they could enjoy one romance-filled night together.

In one of the first indications that Ted thought his feelings give him permission to ignore the wishes of women he likes, the next day Ted decided to track Victoria down. However, in this case, his insistence seemed to work out a lot better. In fact, it seemed liked the only reason things didn’t work out for Ted and Victoria was because she moved to Germany due to her career.

10 Hurt: Ted and Victoria (The second Time)

How I Met Your Mother Ted and Victoria

Victoria was brought back into Ted’s life, 6 seasons after distance came between them. Yet again, Ted pays the price for only thinking about his own feelings. He was willing to get involved with a woman who met him in a bar wearing her wedding gown, despite his anger that Stella left him at the alter.

Ted was paid back for his karmic misdeeds by Victoria. The second time around, their relationship was awful. She had a problem with Ted and Robin being friends, yet wanted her ex-fiance to move in with them. While it was a little bit delicious to see Ted get his just desserts, it was disappointing that Victoria’s return tarnished her earlier time on the show.

9 Saved: Barney and Robin

Initially a pairing that just felt wrong, the idea of Barney and Robin dating seemed to be a betrayal of everything the show had built up to prior to that. However, no matter how things seemed at first, it was a relief that the show at least temporarily put the whole Ted and Robin thing to rest. On top of that, it was really interesting to see two people that had problems with commitment bring a desire to be in a lasting relationship out of one another.

Highlighted by several grand gestures and a whole season about their wedding, Barney and Robin’s relationship was far from perfect, but added a lot to the show.

8 Hurt: Ted and Zoey

How I Met Your Mother Jennifer Morrison

Brought together by their shared appreciation for the beauty of architecture, Ted and Zoey find themselves on the opposite side of a fight over the fate of a building. Given the opportunity to design how GNB will rebuild The Arcadian after destroying much of it, Ted is outraged when Zoey fights to keep the original building intact. In the past, Ted clearly would have sided with Zoey, but he puts his own self-interests first and these two bicker endlessly.

Worse still, Zoey was married when she met Ted. He helps inspire her to leave her husband, even though he knows they will fight over the building, then he breaks up with her over her stance on The Arcadian.

7 Saved: Ted and Robin (Seasons 1-4)

Probably the relationship that most fans think of first when How I Met Your Mother comes up, Ted and Robin were an on-and-off couple that many viewers cared deeply about. It is alos very telling that the show’s debut and final episodes both heavily revolved around this pairing.

When it comes to believing in love, it often seemed like Ted and Robin couldn’t have been more different. Perhaps because of that, when they were at their best, they brought the best out of one another. Either way, as tiresome as the whole "will they or won’t they" thing gets after a while, they drove a lot of the series' plot.

6 Hurt: Ted and Jeanette

How I Met Your Mother Jeanette and Ted

To say that getting involved with Jeanette was a huge misstep for Ted is a gigantic understatement. Jeanette spotted Ted on a train and tracked him down at work the next day. Naturally, the rest of the gang warn Ted that Jeanette seemed like a stalker, but he dismisses that idea. Considering that is the kind of thing Ted has actually done in the past, his trust in her made some sense, but he wound up paying dearly for it.

A police lieutenant who seemed to think her position meant she could get away with unstable behavior, Jeanette flew into one rage after another during their brief relationship. Though played for laughs on the show, her dangerous actions actually were uncomfortable to watch.

5 Saved: Marshall and Lily

Jason Segel as Marshall and Alyson Hannigan as Lily on How I Met Your Mother

Even though the show’s writers sometimes made bad decisions when it came to this couple, Marshall and Lily were undoubtedly the bedrock couple of How I Met Your Mother. Ignoring some of the dubious storylines that were thrown at them, it seems clear how much they adore one another. The chemistry between Jason Segel and Alyson Hannigan was natural, which is why Marshall and Lily felt like friends as well as soulmates.

On top of that, some of the show’s most touching moments revolved around this couple and it would have been an outrage if the show ended without them together.

4 Hurt: Ted and Karen

How I Met Your Mother Laura Prepon

First involved with Ted throughout high school and college, Karen two-timed him at every opportunity and didn’t even try very hard to hide that fact. On top of that, she always carried herself with an air of pretension which inspired Ted to embrace the worst part of his sometimes snobby personality.

Somehow incapable of seeing how awful Karen was, Ted got back together with her as an adult. The only reason he finally left her is that she insisted he cut Lily out of his life. While it was bad enough that Ted ever got involved with Karen, what does it say about HIMYM’s chief protagonist that he never saw her for what she is?

3 Saved: Barney and Nora

How I Met Your Mother Barney and Nora

Nora was the first woman who was able to wrap Barney around her finger after a brief interaction. Right off the start there was something different about Barney's feelings for her. She was able to see through his foolishness and more than happy to reject his advances at first. It was only after some gentle prodding from Robin that Barney a chance with Nora.

A sweet woman who even took care of a sick Barney in lieu of going on their first date together, Nora also seemed to have the ability to see through most of his nonsense. The only downside to their relationship was when Barney inevitably reverted to his old ways and two-timed her.

2 Hurt: Ted and Robin (In the Finale)

Ted Mosby blue french horn series finale of How I Met Your Mother

Given the premise established in How I Met Your Mother’s pilot episode, viewers thought they knew Ted and Robin would not end up together. After all, the entire concept of the show was Ted telling his kids about how he met, fell in love with, and ended up with their mother, but he frequently referred to their "Aunt Robin." Yet, in the latter part of the final episode, it was revealed that the show apparently wanted to have its cake and eat it too.

Despite being shown to be devoted to his children’s mother up until her untimely demise, in the closing moment, Ted yet again threw himself at Robin. It was the ultimate "will they or won’t they" ending and drove many fans to distraction.

1 Saved: Ted and Tracy

How I Met Your Mother The Mother

Finally fully seen on screen in the final episode of How I Met Your Mother’s 8th season, the titular mother had a lot to live up to since she had been teased from the very beginning. Thankfully for fans of the series, she was lovable enough that she lived up to all of the glowing ways Future Ted had described her.

The extremely talented Cristin Milioti managed to make Tracy seem like Ted’s perfect partner while also giving the character her own fantastic independent personality. In fact, the only problems with Ted and Tracy together are that we didn't get to see enough of them-- and that Tracy deserved better than that tragic ending.


Who's your favorite couple on How I Met Your Mother? Let us know in the comments!

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