Romance has always been a big theme in episodes focused on love, relationships, and dating, and the main characters all have different opinions on the subject. However, none of them are experts. During the series, each one of them makes some questionable decisions surrounding their love lives.
It's not always a case of them choosing the wrong mate, either. Sometimes, they're with the right person, but they do certain things in those relationships that aren't smart. Other times, they engage in ill-advised hook-ups which have disastrous effects. Here are some of their worst choices.
Barney Pursuing A Relationship With Quinn
Simply based on the things she says and does, Quinn seems like the perfect match for Barney. Yet, they end up breaking off their engagement because they can't trust each other, and this is something Barney should've realized when they first met.
After all, in their early interactions, she cons him out of a lot of money. At this moment, Barney should've seen the problems they'd eventually face as a couple. But, no, he keeps pursuing her, and it ends in heartbreak.
Barney Hooking Up With Robin Behind Ted's Back
During season three, Barney and Robin hook-up for the first time after she gets dumped by her loser boyfriend again. The incident on its own is fine; they are two consenting adults, after all.
However, Robin's complicated past with Ted makes the whole thing troublesome. As Barney has no real feelings for Robin at the time, he basically risks his friendship with Ted for a one-night hook-up. Once Mosby finds out, he stops hanging out with Barney for some time.
Ted Professing His Love To Robin After Only One Date
Ted and Robin didn't enter into a relationship together until the end of season one, and the ending of their first real night together is a big reason why. After a great first date and some blue instrument-based thievery, Ted says to Robin, "I think I'm in love with you."
These words put a halt on everything and creep Robin out in the process. The very premature declaration of love ends their relationship before it really starts. At least it provides an interesting conclusion to the near-perfect pilot episode.
Marshall Taking The Judgeship Without Telling Lily
While Marshall makes his fair share of mistakes throughout the series, few are romantically related. He meets his soulmate in college, marries her, and they go on to have a wonderful life together. It's not completely smooth sailing, though, as the relationship does have its ups and downs.
One of them occurs in the later years when Marshall accepts a position as Judge even though he and Lily have already planned to move to Italy. He, of course, doesn't consult Lily before making this life-changing decision. It's a rare selfish move from the Minnesota native that almost derails his marriage.
Robin Dating Her Therapist
Dating one's therapist isn't a healthy move. It immediately creates an awkward power dynamic in the relationship, as one person already knows everything about the other.
Yet, Robin makes that exact mistake in season seven when she gets together with Kevin. It surprisingly doesn't have any disastrous effects for her, mainly because Kevin is a good guy. Still, choosing to date him in the first place still ranks as one of her worst mistakes.
Ted Ignoring The Problems In His Relationship With Zoey
Ted and Zoey share some fantastic chemistry together. However, she is still considered among Ted's most hated girlfriends ever. This is because they're constantly at odds over what to do with the Arcadian. Zoey wants to save it, whereas Ted wants to destroy it to make a place for a new building he's deg.
Their differing opinions on the subject is an obstacle that their romance can't overcome. For a while, Ted tries to ignore their differences and push on with their relationship. In the end, though, it breaks the two up. Both of them could've saved each other from a lot of pain by confronting their problems before they truly fell in love.
Ted Moving Too Fast With Stella
After finally getting together, Ted and Stella embark on a whirlwind romance that ends with them getting engaged way too soon. Disaster then strikes as Stella leaves him at the alter to get back with her ex-husband Tony.
It's very unfortunate for Ted, especially as he could've avoided the whole thing. If he hadn't rushed into marrying Stella, he would've found out about her feelings for Tony much sooner, and he wouldn't have been dumped in the most hurtful way possible.
Barney Cheating On Nora
After impregnating a stranger, Barney finishes the show as a single dad. It's not a terrible end for him, but he could've been even happier if he remained with Nora. Besides Robin, she is arguably the woman he cares most about throughout the series. In fact, she's the one who truly pulls him away from his womanizing ways, simply by being sweet and caring.
But, he ruins their relationship by cheating on her with Robin. He then subsequently leaves her to be with the Canadian, who doesn't return the favor. Out of all of his mistakes, hurting and pushing Nora away might be the worst.
Lily Leaving Marshall To Go To San Francisco
At the climax of the first season, Marshall sits outside in the rain, heartbroken because Lily has left him to go to San Francisco. Her reasons for departing are understandable, as she's going to study art, a subject she's always loved.
Yet, she could've left on better by having a proper discussion with Marshall about it. It's not as if he's an unreasonable guy; he would've eventually understood. In the end, the choice backfires, as her time in San Francisco is awful, and she misses her ex-fiancé.
Ted Not Letting Go Of Robin
"There is a reason that it didn't work out between you and me, but it's not , and I'm willing to bet it's the same reason none of your other relationships in the last six years have lasted either. It's Robin." This quote by Victoria perfectly summarizes why Ted's obsession with Robin wasn't a good thing.
He wastes so much of his life pining for her. It's not as, though, they are the perfect couple; their opposite goals in life prove that. Perhaps if he'd have let her go, then he could've avoided constant heartbreak and even enjoyed his love life more instead of waiting until the year 2030 to be with her.