Tough Love: The Worst On-Screen Boyfriends

Romance, everlasting love, and cute couples are the three elements that comprise most of the plots in the movies, and TV shows that we watch every day. Watching on-screen relationships makes us want to have relationships of our own so that maybe we can feel the same happiness and bliss that our favorite characters feel. It’s not unusual to come across people who are die-hard fans of male characters or of a certain relationship — the so-called ships.

Oftentimes, the male characters are loved by the audience, especially when the characters are bad-boys — and also when the actors who portray these characters are handsome. The thing is, sometimes these male characters suck at being boyfriends and their relationships aren’t exactly what we call healthy — even if their fans won’t admit it.

In this article, we’re going to see the worst on-screen boyfriends of all time! Oh, there will be a lot of spoilers from now on, so read at your own discretion!

Chuck Bass, Gossip Girl

Back when Gossip Girl was released in 2007, it was an instant hit. A TV show narrating the dramatic lives of Manhattan’s elite, which was portrayed by the hottest young actors on the scene? Gossip Girl had everything necessary to become a success. 

Not only did we get to see those teens spending tons of money, but we also watched their chaotic romantic lives unfolding in front of our eyes. Chuck Bass, particularly, was the local Casanova. He treated women like objects and even attempted to force himself on a young Jenny. Definitely one of the worst boyfriends we’ve ever seen on TV.

Derek Shepherd, Grey’s Anatomy

Derek “McDreamy” Shepherd, the charming and talented doctor from Grey’s Anatomy, won over the female audience’s heart as soon as the first season of the show premiered back in 2005. He also captured Meredith Grey’s heart shortly after they met for the first time.

The thing about Doctor McDreamy is that he was not a dream of a man — at all. First things first: he was still married to Dr. Addison Montgomery when he first hooked up with Meredith. Asides from the whole Addison-drama and Derek’s cheating streak, there’s also the fact that he wanted to control Meredith’s life and never accepted that she was just as good of a surgeon as he was.

Dean Forester, Gilmore Girls

We all know how Rory Gilmore was an exceptionally intelligent and sweet girl, but she did have her flaws. But we’re not talking about the worst girlfriends here, so let’s focus on Rory’s love life: it sucked. The younger Gilmore girl had a knack for picking the worst boys to fall in love with.

Dean was Rory’s first boyfriend and, at first, he was the personification of the term “perfect first boyfriend”. Until the two of them started dating seriously, that is. Dean was an overly jealous, possessive, and irritated guy who would raise his voice and lose his temper over the stupidest of things. Definitely ‘worst boyfriend’ material!

Ross Geller, Friends

“Friends” is one of the few TV shows that remains immensely popular even though it first aired in 1994 — almost three decades ago! Among the main characters, one that has always been a topic of discussion is Ross: you either love him or hate him.

Even though Rachel loved him, I’m pretty sure most of us wouldn’t endure half of the things that Rachel did. Ross was extremely possessive — to the point of wanting to forbid Rachel from hanging out with her male co-workers —, he was the most jealous guy on the show, and he kept using that lame excuse “we were on a break!” all the time.

John Bennett, Orange Is The New Black

Although inmate Daya and correctional officer John Bennett’s relationship wasn’t the focus of Netflix’s hit show, fans were absolutely in love with their journey and their tale of forbidden love. From the beginning of their relationship to their engagement, we rooted for the two of them all the way.

Well, we rooted for them until Daya got pregnant, and Bennet suddenly vanished from the face of the Earth — even though he seemed more than excited to have a baby with Daya. Sure, we get it that being a first-time parent is hard, especially when your baby mama is in prison. But that doesn’t mean he should’ve fled the town and abandoned Daya and their child.

Mr. Big, Sex and the City

Even though Carrie and Mr. Big ultimately ended up together, we could think of a bunch of reasons as to why they shouldn’t have been endgame in Sex and the City — asides from the fact that at times it seemed like Mr. Big was more in love with the idea of pursuing Carrie than with Carrie herself.

We should probably start by saying that Mr. Big didn’t seem to understand that Carrie was allowed to have other relationships — especially considering that he was married to someone else, and Carrie wasn’t his property! Also, it didn’t look like he considered Carrie’s feelings that much, often doing things without talking to his partner first.

Mon-El, Supergirl

If you ever thought that maybe there’s no ideal man for you on this planet, I have some bad news for you: men from other planets are just the same! At least Mon-El is just like any other trashy man. 

Properly introduced to us in the second season of Supergirl, Mon-El just felt like an overall forced character, almost as if he didn’t fit in the story. To make matters worse, Mon-El inherited all of his planet’s sexist and stubborn ways, often ignoring Kara’s advice or blatantly picking on her.

Lucas Scott, One Tree Hill

Lucas Scott was created to be the nice Scott brother, a character that was meant to be the opposite of Nathan Scott. Sure, Lucas did seem like a nice guy back in the day, but if we stop to think about it, there was so much that was wrong with him — and we just ignored it!

One of the main things that was wrong with Lucas, was the fact that, for a guy who was supposed to be the best guy in the show, Lucas was pretty into being in a love triangle with Peyton and Brooke. Also, he was seeing Peyton even when he was dating Brooke. Would a good guy do that? Definitely not.

Christopher Hayden, Gilmore Girls

Gilmore Girls was a show that was centered around the lives of Lorelai and Rory Gilmore, the most eccentric mother-and-daughter pair on TV. Their connection was really strong, and the two of them were similar in many ways. Including in their taste for men.

Lorelai and Christopher were high school sweethearts, and their love resulted in the birth of sweet baby Rory. While Lorelai was strong enough to be a teen mom, Christopher wasn’t. The first sign that your boyfriend is a douche: he abandons you when you need him the most. To make things worse, Christopher was away for 16 years and suddenly came back acting as if he could fix his mistakes just by being a good friend to Rory.

Dawson Leery, Dawson’s Creek

Dawson Leery is another example of a character whom you either love or hate him. No, he wasn’t exactly a bad guy, but he sure was self-absorbed, and he was the worst when it came to his behavior towards the women in his life. 

Not only was he way too emotional, but he was also utterly selfish in regards to Joey. He loved to make it clear that he was “different” from the other guys, but would still get possessive over Joey and fight for her like a prize. Also, let’s not forget that he was really mean and inappropriate when his girlfriend, Jen, told him about her sexual life.

Jess Mariano, Gilmore Girls

It seems like Gilmore Girls had a long list of bad boyfriends. Just like Rory’s first love Dean, Jess wasn’t exactly the best boyfriend on the planet — although everyone and their mothers seemed to root for the two of them. 

For starters, that boy was unable to understand what the word ‘respect’ meant. Jess was rude to pretty much everyone in Stars Hollow, including Rory and her family. And let’s not get started on the fact that Jess was borderline-aggressive, with his rage fits and all.

Roy Anderson, The Office

Before Pam and Jim got together in The Office, the young secretary dated her high school sweetheart, Roy Anderson. At first glance, one might have thought that the couple must really love each other, thanks to their long-lasting relationship. The truth is: that wasn’t the case, at all.

We could spend all day talking about the countless number of flaws that Roy has. But let’s stick to the most alarming ones. First, Roy never seemed like he cared about Pam as a person; he never even bothered to actually talk and listen to her. There’s also the fact that Roy didn’t put any effort in at least pretending that he was with Pam because he loved her, and not because it was convenient for him.

Don Draper, Mad Men

Mad Men is unarguably one of the most popular TV shows of all time. The series narrated the lives of men and women in the 60s — and let us tell you something: every single male character in that show deserved a spot on our list of the worst boyfriends. But let’s focus on the main character, Don Draper.

First things first: no woman should date a man who has been lying about his own identity for years. Don was also the biggest liar and cheater in the whole show. Although he was married to a beautiful and educated woman and had gorgeous children with her, Don cheated on Betty with pretty much every woman whose life crossed his.

Ezra Fitz, Pretty Little Liars

I suppose that most men in PLL also deserved to be on this list, considering that there were a lot of adult men who felt attracted to teenage girls in this show. The cute English teacher Ezra Fitz was one of them.

After he graduated from college, Ezra (who was probably 22 years old) first moved to Rosewood because he wanted to investigate the disappearance of 15-year-old Alison DiLaurentis — a girl who he had been involved with at some point. Not creepy at all, right? To make things worse, Ezra hooked up and engaged in a relationship with his teenage student Aria, even though that’s forbidden by law.

Pete Campbell, Mad Men

Yet another Mad Men character who is going down in history as one of the worst on-screen boyfriends ever is Mr. Pete Campbell, an ambitious advertiser who wanted nothing but to become the best in his craft. Oh, and did we mention that he was also a horrible husband and treated women as objects?

Pete earned himself a spot on our list right from the very first episode of the show when he showed up on Peggy’s doorstep and spent the night with her — although he was engaged and his wedding was only a few days away. Not only did Pete have a short-lived affair with Peggy, but he also enjoyed tearing her down in front of his colleagues in an attempt to hide his true feelings, which is not cute at all!

George O’Malley, Grey’s Anatomy

Although we feel bad about adding sweet Dr. O’Malley to our list, he sure deserves a spot, no matter how cute he was. As a friend, a colleague, and a professional, George was honestly one of the best guys on the show. But as a lover, he sure had his flaws.

Two moments consolidated George as an awful man regarding his significant others: he cheated on his wife, Callie, and treated her in the worst way possible; he slept with his co-worker Meredith and then proceeded to ignore her. 

Emmett Bledsoe, Switched At Birth

Emmett from Switched At Birth was a living proof that men will suck even if they haven’t gone through difficulties in their lives. The teenager had everything to be one of the best on-screen boyfriends, but then he chose to cheat on Bay. Yikes.

If cheating wasn’t wrong enough, Emmett proceeded to get his girl back…only to be awful to her again! Right when Bay needed him the most, he ghosted her and dumped her after she had been sexually assaulted. Seems like things spiraled really fast for Emmett.

Ted Mosby, How I Met Your Mother

There’s one thing we know for sure: Ted Mosby could’ve easily been a character in a show called How To Get Away With Being A Jerk. This show doesn’t exist, obviously, but Ted still managed to get away with being one of the worst on-screen boyfriends ever.

Maybe we’re part of a minority of people who have decided to call Ted Mosby out on his BS, but even fans can’t deny that he wasn’t the best guy ever. Ted was pretty much obsessed with finding the love of his life — and that made him go after women and never take ‘no’ for an answer. Typical ‘entitled guy’ behavior. And when he did get the girl he wanted, Ted was never the good guy he claimed he was.

Bill Compton, True Blood

We can ignore the fact that True Blood didn’t have the best plot on television. But we can’t ignore that this show had some awful men, who made for particularly bad boyfriends. Bill Compton is the perfect example of this — he’s possessive, dull, manipulative, and a liar.

When Bill was in a relationship with Sookie, he lied to her about being under orders for the entirety of their romance. He dated her for three seasons and didn’t have the guts to tell her the truth. Is there anything worse than that? Yes, there is: he almost killed her, too.

Aidan Shaw, Sex and the City

Although many people don’t understand why Carried ended up with Mr. Big when she could’ve chosen Aidan instead, we think that she would’ve been better off without either of the two! We have already listed Mr. Big’s flaws, and now it’s time to list Aidan’s, too.

Aidan was supposed to be the perfect guy — especially considering that he was meant to be the opposite of Mr. Big. The thing is, the writers’ plan backfired. Aidan was far from being perfect: 1) he wanted Carrie to change so she could fit his lifestyle; 2)  he proposed to her just because he couldn’t trust her anymore and wanted to control her; 3) he flirted with another woman just because he wanted to make Carrie jealous.

Logan Huntzberger, Gilmore Girls

We’ve already stated why Rory’s first and second boyfriends, Dean and Jess, sucked. The former was annoyingly possessive and the latter simply had no respect for anyone. Finally, it’s about time we talk about Rory’s third boyfriend, her college sweetheart Logan Huntzberger.

Logan was a privileged rich boy who was not only extremely dramatic but was also an entitled brat who slept with different girls and proceeded to claim that he and Rory “were on a break”. Let’s not even get started on the fact that Logan cheated on his fiancé in the revival and then got Rory pregnant.

Tristan DuGrey, Gilmore Girls

We’re finally reaching the end of our Gilmore Girls’ bad boyfriends list with Chad Michael Murray’s handsome character Tristan, who was first introduced when Rory started studying at Chilton. Tristan was a player and he wasted no time picking on Rory from her very first day at school.

Although Tristan wasn’t officially Rory’s boyfriend, it was clear that he was in love with her, and they even kissed at some point. The thing about Tristan was that, although he was a teenage boy, he bullied Rory as a way to get her attention — just like 10-year-old kids do!

Fitzgerald “Fitz” Grant, Scandal

One would think that someone as important as the president of a country would be, at the very least, a good husband. Well, that’s not the case in Scandal: Kerry Washington’s character Olivia Pope is romantically involved with the president of the United States, Fitz, but a lot of people don’t understand why — because he absolutely sucks!

In a nutshell, Fitz is a misogynistic, abusive man and it seems like there are only two things that he enjoys doing when it comes to Olivia: sex and yelling. To make things worse, Fitz is selfish and entitled — and he sure loves whining all the time!

Danny Castellano, The Mindy Project

Danny Castellano had three main qualities: he was extremely handsome, he was really nice to his parents, and he was a great father. But one thing that we can’t say about Danny is that he was the perfect boyfriend. 

First things first, Danny could be awfully rude to everyone, including the people he cared about. On top of that, he was actually quite mean to Mindy and didn’t seem like he measured his words sometimes. Remember when he told Mindy that he didn’t see himself marrying Mindy? In front of a bunch of people? Yeah.

Steve Harrington, Stranger Things

Steve Harrington unarguably won over many fans’ hearts over the years — especially thanks to his character development, which is one of the best in television history. As a human being, he is an incredible guy but as a boyfriend, we don’t think he’s that nice. 

Back when Steve and Nancy were still dating, he sure was awful to her. He was insensitive and selfish and never trusted Nancy, even though he was a womanizer. Steve bullied Jonathan because he was suspicious of him and Nancy, and he was pretty aloof. Not exactly the best boyfriend, but thankfully he recognized that later on.

Xander Harris, Buffy

Buffy, The Vampire Slayer was one of the biggest hits in the 90s, and the show nurtured a fanbase that still watches and talks about the show almost religiously. One thing that we can agree on is that after so many years, we can finally talk about some Buffy things that aren’t as cool today — and Xander is one of them.

At first sight, Xander Harris looked like he could be a good boyfriend. He was goofy and it was pretty hard not to like him. And maybe that’s why we all ignored the fact that he made pretty awful jokes about women, and he cheated on Cordelia repeatedly, even though she sacrificed a lot in order to be with him. Oh, and he abandoned Anya at the altar when he was the one who proposed.

Dan Humphrey, Gossip Girl

Maybe we can all agree that Dan wasn’t just one of the worst boyfriends in Gossip Girl — he was one of the worst characters in general! On top of having an annoying “fish-out-of-water” complex, Dan could also be pretty condescending to those around him — especially his girlfriends.

Guys who hide under the ‘good guy’ facade are always the worst, and that’s precisely who Dan was. Remember when Dan found out that Serena had hooked up with Nate before she left town, and proceeded to act disappointed because he thought she was “different”? Sexist much? So not cool.

Owen Hunt, Grey’s Anatomy

What is it with fictional doctors being fabulous in their profession but being awful regarding their personal lives? Owen Hunt is a perfect example of this: he’s a rockstar surgeon, but none of his relationships last for very long — and it’s always his fault.

For starters, Owen obviously had some anger issues, losing his temper over stuff that didn’t call for shouting and harsh words. Also, he was a bit controlling in his relationships, always trying to push his needs before his partner’s. For instance, he openly blamed Christina Yang for having an abortion even though she had always made it clear that she didn’t want kids. 

Joe Goldberg, You

As of 2018, it became impossible to create a list of worst boyfriends and not mention Netflix’s sociopathic character, Joe Goldberg. We can all agree that it can’t get any worse than a guy who stalks your social media and follows your every move?

Joe not only manipulated Beck into falling for him, but he also drove her away from her friends. And if that wasn’t enough, he murdered every single person who stood in his way of getting Beck all to himself. Not exactly the type of guy we would want to date, right?

Alex Karev, Grey’s Anatomy

Over the past 15 years, we’ve watched Alex Karev leave his rude bad boy ways behind himself and become an incredibly talented surgeon. However, no matter how mature he seemed, Karev still had a long way to go regarding the way he treated his love interests.

For instance, when Alex was suspicious that Jo was having a fling with Doctor DeLuca, he got so angry that he beat up the younger doctor, even though he had no confirmation that anything was going between Jo and Andrew. 

Nate Cooper, The Devil Wears Prada

Nate Cooper was possibly one of the worst boyfriends in cinematic history. Maybe he couldn’t handle that Andy had a brighter future than he would ever have, or maybe he was downright sexist and couldn’t bear to see a woman succeeding. 

When we watch this movie, after noticing how terribly annoying and whiny Nate truly is, it’s quite hard to make it to the end of the film. Nate makes light of Andy’s career, disapproves of her new outfits, gets upset when she doesn’t prioritize his birthday over an important work event, and complains that she’s always changing — as if human beings are supposed to stay the same forever!

Kit Carruthers, Badlands

Another sociopathic boyfriend that has made it to our list is Kit Carruthers, from 1973’s neo-noir film Badlands. The movie has since developed a cult following, and Kit remains as one of the meanest villains — and one of the worst on-screen boyfriends as well.

Where should we get started? Maybe on the fact that Kit is ten years older than 15-year-old Holly. Her father obviously disapproves of their relationship, so Kit decides that the man must die. After that, he proceeds to drag Holly with him as they go on a killing spree across Montana.

Danny Zuko, Grease

Although Grease is one of the most beloved movies in America — and features a young John Travolta at his prime —, we have to admit that Danny Zuko was a terrible boyfriend, and he didn’t deserve Sandy at all. 

For starters, Danny doesn’t even feel bad when he lies to Sandy at the beach — we all know he wasn’t planning on seeing her after the summer was over. Also, Danny told his friends a ridiculous story about how he had gotten it on with Sandy, which is an awful and disrespectful thing to do!

Billy Loomis, Scream

Can a guy get any worse than Scream’s Billy? We don’t think so. First of all, no good person goes on a killing spree out of anger because of their parents’ divorce. Billy Loomis was a delusional psychopath and he turned his girlfriend’s life into hell.

Billy not only pressured Sydney into losing her virginity when she was clearly not ready, but he also decided to take revenge on his girlfriend as if she had anything to do with the fact that her mother and Billy’s father had an affair.

Cal Hockley, Titanic

Since the movie premiered in 1997, we have known that Cal Hockley was the worst in Titanic: he was a terrible person and an even worse fiancé — and that was part of the reason why we rooted so much for Rose and Jack.

Cal was snobbish and treated others as inferior to him, solely because he was rich. He also hid his true colors from Rose — until he noticed that she was developing feelings for Jack. Shortly after that, Cal started being abusive and even tried to kill Rose!

Patrick Bateman, American Psycho

Maybe you may have noticed a pattern here: sociopathic characters don’t exactly make the best on-screen boyfriends. As handsome as Patrick Bateman was, he was an awful fiancé — who cheated on his fiancé and didn’t take her seriously — and an even worse lover.

Patrick was conceited and way too vain. On top of that, he was also extremely violent in bed, and he hired the services of prostitutes just so that he could treat them horribly. Oh, and did we mention that he was also a serial killer?

Jim, Edward Scissorhands

Jim from Tim Burton’s Edward Scissorhands was the typical arrogant jock who somehow managed to date the nice girl. Just like many other characters from other films, Jim was technically harmless — until he became jealous of Edward and Kim’s connection.

Blinded by his stupid jealousy, Jim decided that it was his duty to turn Edward’s life into hell — and he never cared about how that would make his girlfriend feel, especially considering that Edward was her friend. When Kim finally dumps him, Jim goes on a drunken rage, which is totally not cool! Boy, bye!

J.D., Scrubs

Sure, we have got to admit that J.D. had the potential of being the perfect boyfriend — and he was pretty good sometimes. But we can’t ignore the fact that J.D. could also be a capital jerk when he wanted to, which is why he earned a spot on our list.

For starters, when J.D. heard Kylie’s story about her ex-boyfriend who had cheated on her, he decided it would be a good idea to lie to her. Not so nice. Also, when J.D. was involved in that weird relationship with Danni, he treated her horribly, instead of simply ending things.

Jason Teague, Smallville

Though it seemed that Jason was truly in love with Lana Lang, we can’t say that he was the boyfriend that Lana had ever dreamed of. Even if we ignore that Jason was probably lying to Lana since the beginning of their relationship, there are other things we can’t ignore.

Let’s begin with the fact that he was an adult man and Lana was just 17 years old when they started dating. To make things worse, he moved to Smallville and started working at the school where Lana studied, which is pretty creepy. And we obviously can’t forget that Jason attacked Clark after he got jealous when he saw Clark talking to Lana.

Riley Finn, Buffy

It’s common knowledge that Buffy had an awful taste in men. And we also know that the writers of the show would have a very challenging time coming up with another love interest for Buffy after Angel was gone. Riley was supposed to be the perfect guy for Buffy — except that he wasn’t.

Perhaps there will be a day when screenwriters realize that good guys don’t necessarily have to be boring. Riley Finn, as nice as he was in season 4, was the ultimate boring boyfriend. In addition to that, Riley simply couldn’t handle that Buffy was a strong woman — and no sexist guy is a good boyfriend, ever!

Damon Salvatore, The Vampire Diaries

Although Damon and Elena were the main romantic pairing in The Vampire Diaries, we can easily point out a few of Damon’s character traits that make him one of the worst boyfriends on television. Starting with the fact that Elena was originally his brother’s girlfriend.

Also, Damon and Elena’s relationship wasn’t one of the healthiest. Elena herself couldn’t explain exactly why she stuck with Damon. And even if she mostly ignored it, we all know that Damon was actually pretty violent. For instance, He would go on killing sprees at the slightest spark of jealousy, which is totally unacceptable. 

John Willoughby, Sense and Sensibility

Willoughby was a terrible character both in the novel by Jane Austen and in the 1995 British movie that was based on the novel. He was basically a wolf in sheep’s clothing, and that made him a terrible boyfriend to poor Marianne.

Marianne and John spent a lot of time together after they meet for the first time, and the young woman falls for him. And guess what John gives her in return? He abandons Marianne and flees to London, where he married a rich woman. When Marianne discovers this, she finally realizes what we all guessed from the start: John Willoughby only ever cared about money.

Lex Luthor, Smallville

In Smallville, Lex was more than just an evil villain: he was also Clark Kent’s rival regarding Lana Lang. The thing is, Lex knew how much Clark and Lana cared for each other, and he even tried to help his friends get together. And then everything changed.

First of all, Lex hired someone to break Clark and Lana apart. And when he got what he wanted, Lex started hiding things from Lana, instead of confiding in his partner. Oh, and he was also injecting Lana with hormones to make her believe she was pregnant. That’s not the way to keep a girl by your side, dude!

Steve Wood, Dead to Me

Although Judy couldn’t resist Steve’s charms and often overlooked his obvious flaws, viewers had no problems noticing how bad of a fiancé James Marsden’s character truly was. From his connections to the Greek mafia to his habit of belittling Judy, Steve Wood was the worst boyfriend ever.

Personally, we believe that asides from his other issues, there’s one thing that made Steve Wood earn a spot on this list: he left Judy because he couldn’t handle the fact that she couldn’t have children! Your fiancé just had yet another miscarriage and you decide it’s the perfect timing to leave her? Not nice at all, Mr. Wood.

Noah Flynn, The Kissing Booth

Noah Flynn and Elle Evans are a fan-favorite couple in Netflix’s hit movie The Kissing Booth. And because they are a couple that most people adore, maybe we’re taking a risk by stating that Noah sucks as a boyfriend. 

For starters, Noah doesn’t take Elle’s feelings into consideration after he moves to Boston for college, when he knew that Elle was feeling pretty insecure about their long-distance relationship. On top of that, he lied to Elle about his friendship with Chloe — because he knew that their proximity was not exactly a good thing.