Worst TV Boyfriends: The five least dateable guys on your favorite TV shows

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If you read last week’s post about the Most Date-able men on TV, you probably figured I’d do a follow-up cataloging the guys on the other end of the scale. And as much as I hate to be predictable, you were right.

So, here are the worst TV boyfriends – my top 5 picks for the characters you’d want to swipe left on.

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Worst TV Boyfriends

1. Ross Geller – Friends

Sure Chandler has commitment issues and Joey is a total womanizer, but it’s Ross who takes the title of Worst Boyfriend on Friends.

We all remember how he slept with the girl from the copy place almost immediately after a fight with Rachel. To be fair – they were on a break, so we can all put that debate to rest. But that still doesn’t excuse Ross for his actions!

After all, Rachel suggested taking a break in the first place because of how whiny and unsupportive Ross was when she landed her dream job. She did have less time for him, but I think we all know the real reason he was upset about her working more and it had everything to do with her handsome colleague, Mark.

2. Ryan Howard – The Office

Kelly may not have been perfect, but she definitely deserved better than Ryan. He cheated on her constantly, broke up with her after getting a promotion, and constantly played this on-again/off-again game with her.

At times, he seemed to find her annoying and acted as if he were “forced” into a relationship unwillingly, but then professes his love for her once she finds someone else. He was like a jealous toddler – he only wanted her back when she wasn’t available.

Plus, he treated women in general as objects and constantly acted like a fuckboy. Remember how he tried to hit on poor, innocent Erin? He was basically every girls tinder nightmare.

3. Big – Sex and the City

For one thing, I’m a huge Caidan shipper (that’s Carrie and Aidan for those not well-versed in made-up couple names), so the fact that the show’s heroine ended up with anyone other than this sweet-natured craftsman is a crime in and of itself.

But the fact that she ends up with Mr. Big?! Ridiculous. I know a lot of people found him mysterious and charming – personally, I found him arrogant and sketchy as hell.

First he tells Carrie that he doesn’t want a committed relationship. Then he goes and marries a younger woman. I mean… ?

Oh, and the whole thing in the movie – where he just decides not to show up to their wedding, leaving her humiliated in front of everyone she knows?

Let me repeat – He. Didn’t. Show. Up. To. Their. Wedding.

If that’s not a total dick move, I don’t know what is.

4. Michael Kelso – That 70’s Show

This one’s probably pretty obvious to anyone who’s ever watched the show, but Kelso is just the absolute worst.

He’s incredibly shallow and stupid – two things that should be deal-breakers right off the bat. But then, on top of that, he’s a terrible boyfriend. He cheats on Jackie All. The. Time.

Then, as if that’s not enough, he starts dating another girl (Annette – played by the beautiful Jessica Simpson) just to make her jealous.

Like his millennial counterpart, Ryan Howard, he seems to only want Jackie when she’s with someone else – always preventing her from truly being happy.

5. Don Draper – Mad Men

In all fairness, I think Don was always meant to be an anti-hero. The show is about him and the fact that he is, above all else, a flawed and broken man. But I couldn’t leave him off this list. Without a doubt, he’s one of the worst TV show boyfriends.

In every single relationship he has on the show (which is a LOT), he’s an asshole. He’s never faithful. For a minute there, it seemed like he might actually be monogamous with his second wife, Megan, but then, as soon as Sylvia comes along, he’s back to his old ways.

He’s also controlling and jealous – remember when he sabotages Betty’s chance of being a model because he wanted her at home full time? And then basically called Megan the equivalent of a prostitute for the fact that her television role involved kissing another guy on screen? ?

Yeah. Because that’s what’s problematic for a marriage, Don.

The show’s finale seemed to end on a note of hope, but after watching how Don behaved for seven seasons, I’m not convinced he’ll ever change.

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Worst TV Boyfriends Conclusion

So there you have it! Five of the worst boyfriends the small screen has to offer. Now it’s your turn. Who’s on your list of undateables? Leave a comment below and let me know your take on worst TV show boyfriends.

And tune in next time for how I’d rank the ladies of television.

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5 Worst TV Boyfriends


  1. avatar

    I immediately thought of bad-boy Don Draper, but I think seemingly-sweet Ross Geller is worse!

    1. avatar

      That’s a great point – he seems like a good guy, which makes his bad behavior even worse.

  2. avatar

    I’ve only watched Friends in this list and high-key agree! Also I am one who doesn’t understand why people like Friends lol. So that entire show is a no for me.

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30ish Lifestyle blogger, relationship "expert," and modern-day agony aunt.
Sometimes humorous, always honest.