Gossip Girl: 10 Boyfriends, Ranked From Worst To Best

Gossip Girl is a series that is most known for its romantic relationships. Being the CW Soap Opera that it is, when it comes to these couples we are able to smell drama from a mile away. Saying Gossip Girl is "dramatic" is a bit of an understatement, considering all that has gone down on The Upper East Side with Manhattan's finest elites. While the girls on the show can be incredibly cruel, the boys on Gossip Girl take the crown for being even worse. Some of the men on GG were genuinely good people who didn't get the on-screen attention that they deserved. Most of them, though, were impressively terrible.

Speaking of the men on Gossip Girl, let's take a look at the boyfriends of the series ranked from the absolute worst to the absolute best. Shall we?

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10 Chuck Bass

Blair: I love you

Chuck: Well that's too bad.

Back in the day, Chuck Bass was known by Gossip Girl fans as the misunderstood heartthrob. Sure, he was both physically and verbally abusive towards his girlfriend Blair. Sure, he pimped her out to his uncle in exchange for a freaking hotel- But have you seen his jawline?

Is that boyfriend material or what?

We have been excusing Chuck Bass as the bad boy who's simply "misunderstood" for far too long. He is not misunderstood, he is just a straight up terrible person. He tried to force himself on both Jenny and Serena in the pilot episode. Are we supposed to let that slide because he's got fairly decent hair and a half-assed sort of charm? Chuck Bass isn't the kind of "bad boy" that "needs to be fixed". He is a downright mean-spirited person who tries to buy Blaire's love all the time with expensive gifts when he could just, you know, apologize for being a major a-hole all the time. Seriously. It's like a 24/7 job for him to constantly be the worst person in the room.

Fans of Gossip Girl have been admiring Chuck and Blair's dynamic for over a decade, labeling the two of them as "relationship goals". Since when has it become a "goal" to find a man as selfish and controlling as Chuck? Sure, Chuck and Blair a.k.a "Chair" had strong chemistry throughout Gossip Girl, but chemistry doesn't keep you warm at night, now does it? Chemistry isn't there to emotionally support you or provide you with any sense of security. We are older now and wiser since the days of Gossip Girl being on air. Hopefully, we can now see that Chuck is so far from being "goals" and is pretty much the worst boyfriend ever.

RELATED: Gossip Girl: 20 Things That Make No Sense About Blair And Chuck’s Relationship

Chuck (to Blair): You held a certain fascination when you were beautiful, delicate and untouched. But now you're like one of the Arabians my father used to own. Rode hard and put away wet. I don't want you anymore and I can't see why anyone else would.  (WTF?)

9 Dan Humphrey

Oh, Dan... What are we going to do with you? Why do you see yourself as such a "nice guy" when you're actually the worst? Is it because you're a writer? Do you think being a writer makes you "sensitive" and somehow excuses you from being a terrible person? Well, guess what Dan? Hitler was a writer too.


RELATED: Gossip Girl: 20 Things That Make No Sense About Dan Humphrey

The fact that Dan has been lying to not only his friends but his "true love" this whole time about being Gossip Girl is only half of the problem here. It's not like he was revealing through Gossip Girl all of the good deeds his friends have done. Dan only reports on his friends in the worst light, always ready to spill the tea regardless of how much it humiliates the people he is supposed to be looking out for. He makes Serena out to be a hot mess on GG, shaming her multiple times throughout the series just so his blog can continue to thrive. Imagine how cheated Serena must feel! Not cool, Dan. Not cool.

8 Tripp Vanderbilt

First of all, his name is Tripp. If you are going to go on living with the name "Tripp", especially the name "Tripp Vanderbilt", you can't expect us to trust you as a human being. His name sounds like it would belong to the bad guy in an 80s movie.

All roasting of his name aside, Tripp V is not an amazing person. First of all, he is a full grown man and he still chooses to obsess over Serena, who can't be older than 16 during the height of his infatuation. If that isn't bad enough, Tripp is a married man! Despite Vanderbilt being a politician in the spotlight, he still chooses to pursue an affair with Serena. Lame move, T.V!

7 Carter Baizen

Gossip Girl Serena Carter

Blaire warns Serena that, "guys like Carter don't change," and she is right about that. When Carter and Serena begin to date, all seems peachy. Although Carter does seem to truly care about Serena, the way he goes about keeping her around is pretty manipulative. Carter lies to Serena about knowing where her father is when he really doesn't, just to keep her around. If you want to keep a lady interested, why not invest in a nice cologne? No need to lie to her about knowing her father's whereabouts.

6 Gabriel Edwards

Gabriel Edwards, portrayed by Armie Hammer, was one of Serena's brief boyfriend's who was basically scamming her the whole time. While they dated, Serena claimed Gabriel was impossible to make plans with because he was always ignoring her calls. Turns out, he had been seeing his supposed "ex" the whole time, Poppy, who was not really his ex. The two never broke up. Poppy and Gabriel were both using Serena as a part of a larger Ponzi scheme. How romantic!

It was a strange little plotline, and their relationship was just unnatural throughout.

5 Nate Archibald

Chace Crawford as Nate Archibald in Gossip Girl

As pretty as Chase Crawford may be, I've seen dish rags with more personality than Archibald. This Troy Bolton wannabe is about as interesting as a wet carrot, but then again, I don't want to insult wet carrots. It doesn't matter how long his eyelashes are, Nate Archibald is too bland to ever be labeled as a fantastic boyfriend, period. The only reason he's lower down on this list is due to the fact that he has never compared any of his girlfriends to one of his fathers "Arabians", he has never tried to rape anyone, and he has never created a gossip blog in secret while targeting the ones he loves most. In the world of Gossip Girl, he is a decent fella. Being a "decent fella" in Gossip Girl basically means you aren't sociopathic. So, congrats Nate!

4 Jonathan Whitney

Gossip Girl Eric Jonathan

Remember Jonathan? He was the poor kid who got stuck in the middle of Jenny Humphrey's whole angsty teenage power struggle. Jonathan, portrayed by actor Matt Doyle, was Eric's boyfriend for a short amount of time before everything took a turn for the worse. Eric and Jonathan were going on just fine until little J decided to pour yogurt on Jonathan's head for questioning her ego after she became queen B. The violence involving food products didn't stop there.

RELATED: 10 Couples That Hurt Gossip Girl (And 10 That Saved It)

Jenny tells her followers to egg Jonathan while he's on his way to visit Eric, and they go ahead and do it. This poor kid can't catch a break! After Eric seeks revenge on Jenny for putting his main-squeeze through all this food-related torture, Jonathan breaks up with Eric in an effort to escape the drama. Poor kid! He was too good for all of these children.

3 Vanya

Vanya is Dorota's love interest on Gossip Girl. He is also one of the purest of souls to enter the series. He is known in the show as the Van Der Woodsen's doorman. Although his job requires him to hold doors, his personality holds our hearts. Too cheesy for yah? Too bad. Vanya deserves all the cheese. Dorota and Vanya end up getting married and go on to have a daughter named Anastasia, officially making the three of them the most adorable family on The Upper East Side. We all know Vanya and Dorota are the real OTP of Gossip Girl.

2 Rufus

Matthew Settle as Rufus Humphrey in Gossip Girl

Rufus may not have the wealth of those on The Upper East Side, but what he lacks in the Fitzgerald style of luxury, he makes up for by being an incredible boyfriend/lover to Lily. Rufus has been patiently waiting for Lily for twenty long years, and it's no secret that he has been in love with her the whole time. It's so nice to see the two of them on screen because we get to take a breather from all the cheating and lying going on with the core characters. Thank you, Rufus, for actually listening to your woman's wants and needs!

RELATED: Gossip Girl: Guest Stars, Ranked

Plus, it is rumored that the two actors who play Rufus and Lily are dating IRL. How cute is that??

1 Cyrus Rose

Wallace Shawn as Cyrus Rose in Gossip Girl

Cyrus Rose is not only the best boyfriend on Gossip Girl, but he is also the best person on Gossip Girl. There is no fresh snow on earth that is as pure as Cyrus mother effin Rose. If he is able to humanize his wife Eleanor and his stepdaughter Blair, he deserves all the praise this world can offer. He truly makes Eleanor happy, something we honestly thought would never happen. He is always loyal to Blair and treats her as though she were his own daughter. Cyrus, congrats! You are the true gem of Gossip Girl and we can only hope to one day find a person who is as kind as you are.

NEXT: Gossip Girl: Characters Sorted Into Hogwarts Houses

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