Gossip GIrl: The Male Characters, Ranked By Their Romantic Partner Potential

The Gossip Girl had a lot of characters throughout its six-season run. Allies, schemers, traitors, and friends, all came dancing into the lives of Serena and company. However, most of them were recurring or guest stars, and for the most part, the show kept the same core of six or seven mainstays during all 121 episodes.

The show is infamous for being a not-so-great representation of wealth and power, and some of the male characters definitely come off as manipulative and controlling. However, some act in a kinder, more decent way, proving that in the Upper East Side, not everything is games and betrayals. Please note, this list takes a look at the characters with the understanding that they aged throughout the show and finished the series as adults.

9 Bart Bass

Bartholomew “Bart” Bass is a pretty horrible human being. He’s cruel, ambitious, cunning, shameless, ruthless, and pretty much capable of anything to get what he wants. At many points in the series, he shows his awful true colors, manipulating everyone around him, keeping secrets, and even trying to have his own son killed.

Bart is, without a doubt, the worse person in the show because he actually fits the common definition of “evil.” He’s not simply a schemer like some of the other characters, he’s actually a dangerous sociopath that represents everything that’s wrong with the Upper East Side.

8 Jack Bass

The Bass family is truly rotten to the core. Bart’s younger brother, Jack is as shameless as his other two blood relatives, but he’s far less serious. A libertine with a flair for the dramatic and a very particular panache, Jack is almost like a teenager. He enjoys toying with his nephew, even engaging in petty games just to spite him.

Jack is not as evil as Bart (no one is), but he’s no prize either. Even though his allegiances fluctuate over the show, Jack only cares about himself and will always do what’s best for him.

7 William Van Der Woodsen

A much better father than Bart, but still quite worse than Rufus or Cyrus, William is rather selfish and arrogant. He does care for his family, at least, just not enough to put them above everyone else. William actually does a lot of damage to his children, especially Serena, who’s left with a severe case of abandonment issues after he leaves.

William is ultimately a bad husband because he’s too unreliable and self-absorbed to ever truly care about anyone but himself. His actions are erratic, his talent for lies, disturbing, and not even his most charming qualities can redeem him.

6 Dan Humphrey

Dan Humphrey could very well be a sociopath. He’s someone who lied to those closest to him for years on end, pretending to be their friend while plotting new and different ways to denigrate and expose them, only to finally reveal himself as the orchestrator of their humiliation in a somehow successful effort to win their respect in the last season of the show.

Dan is a narcissist who believes he’s morally superior to his rich and privileged friends while slow and steadily sneaking his way into their lives and lifestyles. He’s someone willing to write a scathing expose about the woman he claims to love, just so he can get the power he so craves for. Someone so selfish could never be a caring boyfriend.

5 Chuck Bass

Chuck starts the story as an entitled creep who thinks he’s better than everyone else just because he has money. Over time, the show goes to great lengths to redeem his character, even going so far as to turn him into a tragic hero. It doesn’t quite work, but Chuck does become less of a horrible human being.

Still, he never atones for his many crimes, he simply gets a free pass by those around him because “they don’t judge.” His tragic, toxic, romance with Blair throughout the later seasons of the show shows that he’s not dependable or stable. Not to mention, his dangerous, risky lifestyle will always end up dragging his significant other to his sick and violent games, just like he did with Blair when she got kidnapped by his business rival in season 4.

4 Louis Grimaldi

When first introduced in season 4, Louis comes off as a pretty nice guy. He’s sweet, attentive, loving, and understanding. Perhaps too understanding, actually. Indeed, he accepts Blair’s close relationship with Chuck and forgives her more than once when she does some rather inappropriate things with her ex.

By the time he marries her, his patience has run out. And because the writers of the show needed a reason to end the marriage, Louis is turned into a vindictive and cruel man who wishes to stay married just so he can make Blair suffer. It’s a horrible thing to do and makes him an inappropriate life partner.

3 Rufus Humphrey

Rufus is one of the best parental figures on the show. Sure, the bar is not really high in Gossip Girl, but that doesn’t make him any less good of a father. He makes a lot of mistakes during the show, like having an awfully misguided affair with Ivy and allowing Dan to live alone in Brooklyn while he shacks up with Lily in Manhattan.

In the end, though, Rufus is still a caring and loving father who strives to do the best for his children. He’s also ridiculously understanding and tolerant of Lily’s shenanigans and has a calm, rational, and mature mind. He’s not afraid to show his feelings and is an old-fashioned romantic. He isn’t perfect, but he’s still husband material.

2 Nate Archibald

Nate is very much a himbo. Loving, supportive, somewhat vacuous, but always willing to help, Nate famously never sends a tip to Gossip Girl, until the end of season 5, at least. He’s just a regular guy who happens to be extremely handsome and extremely rich, yet somehow doesn’t know what to do with either of those gifts.

Nate has the worst luck when it comes to romance, but he never gives up. In every relationship he has, misguided as it may be, he gives it his all and tries to be honest, like when he confesses his father’s prison situation to Juliet. He even tries to pursue a real relationship with Diana in season 5, because he’s always looking for a real and meaningful connection. He truly cares for each one of his girlfriends, proving time and again that, out of all the young men in the show, he’s the best one.

1 Cyrus Rose

Eleanor Waldorf ends up with the best husband. Cyrus truly is a good person, a loving father who unconditionally supports his children, and a great friend to anyone lucky enough to have him in their lives. During the Vietnam War, for example, he rescued one of his comrades under fire. He’s also close friends with Lady Gaga, who was inspired to write “Poker Face” after playing with him.

Cyrus is there for Blair, helping and rooting for her every step of the way. A case could be made that he’s more loving towards Blair than Eleanor herself! Sure, he’s not the most attractive of men, but looks aren’t everything and Cyrus is a true keeper. Anyone who meets him agrees that only a little bit of Cyrus is simply not enough!

About The Author

David Caballero
(803 Articles Published)

David is a twenty-eight-year-old Mexican writer and reader. Having studied Marketing in school, he spent three years working a nine-to-five desk job before deciding to pursue a writing career. He now works as a Senior Writer in ScreenRant and does some more freelancing job, talking about the entertainment business he so loves. Currently, he’s also writing his second novel while actively working to get his first one published.

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