Even if we know it never works out, it’s almost impossible to avoid trying a friends-with-benefits situation at one point or another. Luckily for us, even fictional couples can’t avoid this classic trap and can teach us something we need to learn: that they, under no circumstances, actually work. You either start as friends and add a ~physical~ component or started romantically and try to make things more casual for one reason or another. Either way, someone ends up getting their feelings hurt. It’s nearly impossible to remove the romantic component of a relationship once you add it.
So, if you’re tempted to try an FWB relationship for yourself, here are 20 fictional couples who prove that they’re almost never successful…

1. Richard and Monica on Friends

The end of Richard and Monica’s relationship was one of the saddest breakups in the history of fictional couples. They really love each other, but their age difference finally tears them apart when she wants kids, and he doesn’t. When they run into each other later in life, they decide to try and make things work again, but strictly as friends with benefits. Shockingly, the situation didn’t pan out so well. When Monica realizes she still has feelings for Richard, she proposes getting back together. They both realize that nothing has changed, and they won’t work as a couple. *Sigh*.

2. Jess and Sam on New Girl

The relationship between Jess and Sam on New Girl was just another one of the frustrating stepping stones in the way of Jess and Nick’s love. Although Nick and Jess are one of everyone’s favorite fictional couples, they had to go through a few annoying flings to get through it. Specifically, Jess and Sam’s short-lived friends with benefits situation. Jess obviously has feelings for Nick, but Sam has feelings for her. She ends up cheating on him, and they get back together one last time before she finally admits her feelings for Nick. It was stressful.

3. Shawn and Angela on Boy Meets World

The story of Shawn and Angela is one of the most tragic examples of fictional couples that never were. Boy Meets World was an emotional rollercoaster from start to finish, but the romance between Shawn and Angela was especially turbulent. They finally admit that they have feelings for each other, but decide to see other people and remain friends when they go to college. It’s a constant back and forth of wanting to be together for real, but not being sure how to tell the other person. When they try “no-strings” sex, Shawn realizes he’s still got it bad for his ex and Angela ends things during the makeout session. Eventually, Angela marries someone else in Girl Meets World.

4. JD and Elliot on Scrubs

We can all agree that Elliot and JD from Scrubs are one of the most exhausting fictional couples ever. Their relationship is so on-again-off-again, and it seems like they only realize they like each other when the other has moved on. At one point, they realize they aren’t really working as a couple, and decide to be “sex buddies” instead. Of course, by the end of the episode, they both realize that they care way too much about each other to be FWB only. For the time, they agree just to be friends. Later, they end up together. Either way, another case of a failed friendship with benefits.

5. Zack and Miri in Zack and Miri Make a Porno

As far as fictional couples go, Zack and Miri’s relationship was so great because their situation was just so bizarre, and obviously made for a great movie. In Zack and Miri Make a Porno, two friends and roommates find themselves with almost no money and rent to pay. How do they decide to make some extra cash? By making a pornography together. Of course, when it’s time to get down to it, they realize they may have had feelings for each other all along. Technically not a casual friends with benefits situation, but still, — friends with pornographic benefits doesn’t work either.

6. Jerry and Elaine on Seinfeld

Jerry and Elaine from Seinfeld are one of the most confusing fictional couples of all time. While we know that they dated in the past, the series starts with them being purely platonic friends. As the series goes on, however, this gets pretty complicated. In one episode, “The Deal,” they attempt being friends with benefits. This is almost immediately ruined when Jerry gives Elaine a thoughtless birthday gift of $182 in cash. They realize it’s too difficult to remain platonic while having sex, so they end their “deal,” and continue just being friends. But, it’s pretty clear that these two will always have feelings for each other.

7. Dylan and Jamie in Friends With Benefits (Film)

As you can guess, this movie is all about the difficulties of being friends with benefits. Friends With Benefits follows Dylan and Jamie (played by Justin Timberlake and Mila Kunis), who think they can continue their platonic friendship while engaging in a sexual relationship. However, they travel to California together, get in a few pretty serious arguments, until finally Dylan realizes he loves Jamie. They finally admit their feelings for each other and end up together after a super-cheesy flash mob scene. It’s honestly rom-com gold but obviously the point of FWBs is not to fall in love, so, fail.

8. Ben and Sara on Friends with Benefits (TV Series)

While not based on the aforementioned film, the series Friends With Benefits follows a pretty similar narrative to the movie. Both fictional couples try to navigate their tricky FWB situation, but in the TV show, we follow Sara and Ben as they try to stay friends with benefits, while each pursuing totally different romantic paths. Sara is ready to settle down, while Ben is all about playing the field. However, the show was canceled after its first season (potentially because it’s almost identical to the movie), but Ben and Sara constantly go back and forth on who’s feeling like making things more than just ~physical~.

9. Chloe Sullivan and Oliver Queen on Smallville

Even on a show about superheroes and evil villains, the fictional couples in Smallville aren’t able to avoid very real romantic problems. In particular, the relationship between Chloe and Oliver shows that even the Green Arrow (a superhero!) can’t make a friends-with-benefits situation work. Their friendship was always extremely close and intimate, but it certainly had its fair share of drama and disagreements. Once they become each other’s partners in the Justice League, they realize they have always been more than friends. They try to engage in a casual sexual relationship to maintain a solid partnership, but it obviously falls apart. Once love conquers, they end up as a happily married with a child.

10. Carrie and John on Sex and the City

There are a whole lot of messed-up, fictional couples to choose from in Sex and the City, but none exemplify friends with benefits better than Carrie and John. Although we always knew that Carrie and Mr. Big would end up together, we had to watch a whole lot of nonsense before they realized it. Enter, John. He basically acts as a band-aid for Carrie whenever she’s lonely. They hook up every time she feels lonely just to boost her self-esteem, with no strings attached. It’s pretty messed up, and totally falls apart when they decide to get dinner together. There’s zero chemistry, and they both realize they’re kind of wasting each other’s time.

11. Santana and Brittany on Glee

Finally, some LGBTQ+ representation for fictional couples! Brittany and Santana were one of the most complex relationships on Glee, mostly because every Gleek just wanted them to be together so badly. The show did a pretty good job covering how difficult it can be for two best friends to realize they have feelings for each other, especially when both aren’t out as being queer in any way. Santana and Brittany clearly have feelings for one another, which entirely complicates their status as best friends who occassionally hook up. Luckily for fans everywhere, the two end up getting married.

12. Kelly and Ryan on The Office

Kelly and Ryan are one of the best examples as to why being friends with benefits almost never works. Not only were they one of the worst fictional couples ever, but Ryan was also just an awful human being. Period. Against all odds, they end up together, but that’s not until after Ryan tortured her for years. They would get together; he would treat her badly then end it. Then they would get back together, try to keep it “casual,” then end it. Whenever she tried to end it, he would claim he loved her. Basically, if you can’t figure out if someone loves you, they most likely do not. We’ve all been there, Kelly.

13. Kelso and Laurie on That 70s Show

Kelso and Laurie were one of those fictional couples that nobody liked, not even the two of them. It started as just a casual fling. They would hang out in the Forman’s basement, then hook up in the back of Kelso’s car. This even went on while Kelso was dating Jackie, so yikes. Either way, somewhere along the line Laurie realizes she has feelings for Kelso, and blackmails him into being with her despite the fact that he’s with Jackie. Casual friends with benefits, or a huge disaster waiting to happen? We’re going with the latter.

14. Emma and Adam in No Strings Attached

So this is pretty much just Friends With Benefits (the movie) with Mila Kunis‘ now-husband and Black Swan co-star. It honestly feels redundent to even describe what goes down in No Strings Attached, and is made worse by the fact that both films were released within just a few months of each other. Either way, Emma and Adam, who have been friends for years, decide to starting bangin’ with “no strings attached.” Of course, Adam gets jealous when another guy starts showing interest and everything kind of blows up. First, feelings are hurt. Then, they wind up together. In both scenarios, the FWB was ultimately a failure.

15. Ted and Annie in Bridesmaids

There are few fictional couples with a sex scene as uncomfortable as the one between Ted and Annie in Bridesmaids. They work together, and have a purely physical relationship, although it’s pretty clear that Annie secretly wants more from Ted than just sex. Ted is a huge jerk, though, and kind of treats her like a doormat. Ted and Annie prove that having any kind of ~sexual~ relationship and nothing more is pretty impossible when someone’s caught feelings.

16. Monica and Chandler on Friends

Let’s be honest, we all knew this attempt at being friends with benefits was doomed from the start. Despite lasting plenty of seasons with almost no romantic spark, the chemistry between Monica and Chandler on Friends was totally unstoppable. After they hooked up in London, they vowed it would be the first and last time they interacted as more than friends. Their steamy hookups continued when they were back in the States, and they couldn’t keep apart from each other. When caught in the act, Chandler finally admitted he was in love with Monica. Granted, their friendship with benefits failed, but they are arguably one of the best fictional couples in history.

17. Nicky and Morello on Orange is the New Black

Orange is the New Black is teeming with tons of complicated, fictional couples. While some of them are just looking for a fling to get through their sentence, Nicky and Lorna Morello show truly how difficult that can be. Nicky catches serious feelings for Lorna, who can’t seem to get over her ex. The two remain close friends and continue hooking up, but it doesn’t end well for Nicky, who ultimately is left heartbroken.

18. Brooke and Felix on One Tree Hill

Of course, B. Davis has tried a friends with benefits situation on for size. Lucas broke her heart and she wasn’t ready to be ~vulnerable~ again. But of course, during their no strings attached hookups, both Brooke and new kid Felix started developing real feelings. They become official, just for Brooke to realize that he’s a homophobic piece of trash who spray painted a slur on her BFF’s locker. Bye, boy.

19. Robin and Ted on How I Met Your Mother

When it comes to fictional couples, few are as controversial as Robin and Ted on How I Met Your Mother. They’re constantly on-again-off-again, and date a whole bunch of ridiculous people in between their flings. At one point in the show, Robin and Ted begin a strictly friends with benefits relationship, which drives Barney absolutely insane, due to his feelings for Robin. Ted and Robin have to end the whole thing because they realize the whole thing is just too romantically complicated with their ~history~ and ~feelings~ and stuff. Of course, we know what happens in that series finale.

20. Cordelia and Xander on Buffy the Vampire Slayer

Cordelia and Xander were a couple that definitely didn’t make sense, but had very sweet moments. As part of the Scoobies, the two are constantly put in scary, life-threatening situations, and it’s kind of hot. Of course, Xander and his BFF, Willow, have hated Cordelia since they were children but work with her anyways. Well, hatred is passionate, so their repulsion towards one another quickly turned into an attraction when they were stuck in the basement of Buffy’s house. They end up making out, and proceed to make out several more times in secret until Xander asks if they should just “admit that [their] dating.” Of course, Cordy doesn’t want to go there, saying, “Groping in a broom closet isn’t dating.”
The secret gets out eventually, and the two do end up dating. That’s proof enough that friends with benefits don’t work. If you need another reason to believe it’s bad, the end of their relationship involves Xander cheating on Cordelia with Willow and Cordy getting impaled… after she finds out her BF is hooking up with someone else.

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