The Ten Worst Fictional Boyfriends

Think your boyfriend’s pretty crappy? Well, these craptacular boyfriends will make your guy look like a puppy in a sweater-vest.

1. Tony Soprano, The Sopranos

The Sopranos is probably my favourite TV show of all time (besides The Simpsons). Now you know me a little better, lets hold hands. I came on too strong didn’t I? Aaaaanyway, Tony and Carmela’s marriage was one of the most intriguing aspects of the show. I really disliked the vacuous and opportunistic Carmela but that still doesn’t take away from the fact that Tony was a liar and a cheat. Tony’s treatment of the majority of his mistresses was so terrible that one even committed suicide. All this aside, their marriage was more dysfunctional than a Kardashian family barbeque. They finally form a silent understanding that Tony will continue to provide for Carmela but that means he should also be allowed to play away. And that he does. Honestly, they made my parents look like the Waltons on Prozac. Also, RIP James Gandolfini, you had me at the ducks.

2. Jimmy McNulty, The Wire

Oh dear. Where to begin? He cheats on his wife with a work colleague. He uses said colleague for sex. He has inebriated, sweaty intercourse with random diner girl. He meets a genuinely lovely lady and also fails to stay faithful to her. He also drinks too much. But because he’s Dominic West we kind of forgive him. Damn it, McNulty.

3. Ross Gellar, Friends

Ross seems to be most people’s least favourite Friends character. I genuinely don’t understand this. Not only has he uttered some of the best lines of the entire series (MY SANDWICH??!!) but he also has the perfect mix of funny, nerdy and sweet going on. The problem is is that he makes a pretty terrible boyfriend. Don’t believe me? Lets look at the evidence. First girlfriend after his marriage breakup is Julie, the Chinese palaeontologist. Lets just take a second to appreciate the fact that I spelled that correctly. Ok, moment over. He cheats on Julie with Rachel even though we all totally wanted them to get together. He then cheats on Rachel. You may choose to defend him by yelling ‘they were on a break!’ but you can’t deny that what he did was pretty awful. And also, keep your voice down. My cat’s trying to sleep. Anyway, his escapades don’t stop there. He also treats Mona (no matter how annoying she was) pretty abominably. I know, I know, it’s a comedy. And I probably would have skipped my own wedding (not that I’m married…time to go cry into my cat’s fur) to watch Ross and Rachel finally get together in the final, but there’s no denying he can be a pretty bad boyfriend.

4. Hamlet, Hamlet

Since I teach English (I’d like to take this opportunity to state that the multiple typos are a result of a combination of laziness and stubby fingers, curse you bad genes. And Dad), I felt I’d better insert some old school references in here. As Shakespearean boyfriends go, Hamlet is a bit of a jerk or as I have often opined ‘a whiny indecisive man-baby’. We actually had a debate on whether Ophelia deserved his disdain for agreeing to betray his trust in class with lots of students pointing out that she’s a goody goody who needs to (wo)man up to her father. But when she goes genuinely mad and dies, you can’t help but feel sorry for her. And you also can’t help but blame Hamlet. I mean if someone yelled ‘get thee to a nunnery at me’ I don’t think I’d ever get over it.
Honourable mention has to go to Macbeth also. The weasel.

5. Carlo Rizzi, The Godfather

Remember Connie’s husband? He beats her, he cheats on her and he also contributes to her brother’s death. Somehow I don’t think he’ll be winning ‘Husband Of The Year’ any time soon. I think I’m going to go watch Sonny beat the crap out of him for the hundredth time. Be right back.

6. Cal Hockley, Titanic

Cal is like a panto villain; that is, so evil I don’t know how anyone like him could exist in real life. Selfish, greedy, materialistic and just downright mean (“why Dawson, you could almost pass for a gentleman.” I mean, talk about BURN!). Ok, so there are plenty like him, but they’re usually blond and called Tiffany. His treatment of Rose is so bad that she would rather risk a life of destitution than be his wife. The wig probably doesn’t help either.

7. Edward Cullen, Twilight

I’m not going to waste time dissecting his character because it might give credence to any belief that this character has any semblance of depth. But the guy is a possessive, whiny buzz-kill. He needs a herbal tea and a warm bath.

8. Christian Grey, Fifty Shades Of Grey

Basically, see above. Also, spare a thought for concept of feminism. It was nice while it lasted.

9. Nate, The Devil Wears Prada

This guy. One of my biggest pet peeves is when you’re watching a TV show/film and a character basically acts like a selfish douche and NOBODY seems to see it. In fact, he actually makes Anne Hathaway’s character (Andy) feel as if she is in fact the titular devil in Prada.
Ok, so Andy has her faults. She also comes very close to cheating on Nate with guy with questionable scarf taste/sexual orientation. It’s not just her fault that their relationship starts to suffer, it’s also his lack of understanding about the pressures of her job. She’s in a really really tough job. Cut the girl some slack. She’s under so much pressure that we fear she might just explode. Or suffer some kind of medical emergency. But that wouldn’t have been very glamourous. There’s two events in this movie that drive me crazy. Crazy because we’re suppose to believe that Andy is the villain in both instances when really the people around her are not being very considerate. One is when her friends and boyfriend start throwing her phone around the table when her crazy boss is calling her. Sometimes my friends can be kind of mean to me, and I once glued my friend’s face to a table, but hers come across quite petty in this scene. She’s just given them free stuff. Free DESIGNER stuff. She’s stressed. Her boss rings and they take her phone from her, adding to her stress. The worst part is is that we the viewer are supposed to believe her reaction is over the top, when really she only half-heartedly calls them ‘assholes.’ Which they kinda were.
The next incident shows how her boyfriend obviously has ovaries because he gets a case of PMS so bad, I want to hand him a hot water bottle and a blanket. Andy has a huge work thing and can’t attend his birthday. Don’t get me wrong, birthdays are special and all. But unless you’re seven years old and call your father ‘daddy’, you have to understand that sometimes not everyone will be able to drop all their plans on your birthday. Andy makes a really big effort to get home to Nate on time. She even turns down a chance to meet an influential editor and leaves the event. She brings home a cute cupcake. What does Nate do? He pulls the trick your parents pull on you when they want you to feel really bad. He’s not mad, just disappointed. Ugh. Now why am I taking such issue with a fairly mediocre and frankly forgettable film? Because it basically suggests that career women are very very selfish and can no way manage a career *and* a boyfriend. Our purpose in life as women is clearly to bake birthday cakes for our boyfriends and wait at home for them to call in case there’s a social occasion we’re needed at. *Stares wistfully at phone.*

10. Wickham/Willoughby, Pride and Prejudice/Sense and Sensibility

I have always found these Jane Austen characters to be very similar. Wickham is probably the worst of the two but because Marianne Dashwood’s heart ends up in a million pieces when Willoughby abruptly leaves her, he also deserves a mention. Both men are handsome and charming. Both men are also deceptive and secretive about their shady pasts. The only people who know their true intentions are their respective love rivals, Mr. Darcy and Colonel Brandon. Both men end up married to someone else, the cads. Wickham’s punishment is that he marries Lydia Bennett, aka the most detestable female character ever. Willoughby’s punishment is that he has to see the woman he did truly love marry someone far more deserving of her. Neither of these are exactly ‘please wife me’ material.

So there you go. Now go hug your boyfriend. I’ll lurk in the bushes.

5 thoughts on “The Ten Worst Fictional Boyfriends

  1. weight2lose2013 says:

    How about Van Gogh? What girl wants her boyfriend to hack his ear off because he’s in love with her? If he’s not top ten, then he’s number eleven. 🙂

  2. Yawn says:

    I know this article is old but I saw this movie on cable tonight and wanted to stab my TV (devil wears prada). My ex wife and I both had demanding jobs/bosses and the first thing we agreed on was “work comes first”. There was never any question about that. Phone rings pick it up. Gotta work late? Unlucky.

    The two scenes you mention infuriate me. So much so that whenever i bump into this movie I make sure to pause it for 5-10 minutes on TiVo, walk away, then watch the movie…. Simply so I can FF past these two annoying scenes. I mean seriously the douche waits up for her then when she finally gets home he goes to bed… Such a chick passive aggressive thing to do (no offense)….

    Anyway… Google led me here and I’m happy my first click brought me to a like minded opinion.. Wanna be my third ex wife? Wait… That came out wrong 😛


    • janeybgood says:

      I could not have loved this comment any more. You get me, you really do. I have been ranting about this movie to everyone since it came out and no one seems to see it! And you’re right; he’s the queen of passive aggressiveness. I would say king but…you know. The message of the film is probably supposed to be that you should never let a career come between you and those you love, no matter what you have to sacrifice. The thing is, the message of the film comes across as “you’re completely selfish and horrible if you want to be successful and it’s okay for people to resent you for it.” It’s so frustrating!
      Ha, I would love to be someone’s ex wife!

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