Ranking All Gossip Girl Relationships Based On Normalcy

Ranking All Gossip Girl Relationships Based On Normalcy

Everyone watched “Gossip Girl” in high school, and I do mean everyone. As a girl, it became a thing to define yourself as either a Blair or a Serena. I guess technically you could’ve also been a Vanessa, but honestly, who would’ve ever wanted that. We all lived for the show, salivating over the beautiful clothes, shoes, bags, and people. And then there were the relationships. Over the course of six seasons, the main characters found love in a variety of places with an assortment of hot people (seriously, how was everyone so fucking hot?). We all had our favorites, Chuck and Blair more than likely being at the top of that list. I’d call you a liar if you never once considered them to be #goals.

And then I re-watched the “Gossip Girl.” As an older, hopefully more mature, semi-responsible adult, I couldn’t help but noticed how extremely and completely fucked up all the relationships are. I mean seriously, not only are these relationships not #goals, but rather a warning of what to avoid. From multiple teacher-student affairs to affairs with married people to sex with minors (hello statutory rape), GG had it all. In the spirit of all the terrible relationships Gossip Girl brought us throughout the years, I thought it’d be fun to rank main character relationships*** on a scale of ‘normal and acceptable’ to ‘how the fuck aren’t you in an insane asylum or jail for this relationship?’. Let the fun begin.

**Main characters include Blair Waldorf, Serena Van der Woodsen, Jenny Humphrey, Chuck Bass, Nate Archibald, and Dan Humphrey. The relationships being ranked are only the committed relationships throughout the show and do not include any flings or one time hook-ups.

30. Blair & Nate
The most normal and non-offensive relationship on the show. The most interesting thing about this couple happens when they break up, i.e. the beginning of the craziness that is Chuck and Blair. Blair and Nate were just a high school couple trying to defy the odds and make it work.

29. Serena & Nate
Again, a pretty standard couple. Sure, S and N cheated on Blair back in high school, but that honestly just makes them more relatable. They are just two genetically blessed people who want to sit around and bask in their awesomeness.

28. Dan & Vanessa Abrams
Another fairly average and not all that exciting couple. They were best friends growing up, had the same quirky interests, and were both outsiders looking in. As with all things Dan Humphrey, this relationship is not that interesting.

27. Nate & Vanessa Abrams
Ostensibly this is a couple without too much drama but it’s still an awkward as hell match. I mean this is Nate Archibald – if you didn’t awaken any untapped sexual desires you have then you’re psychotic. Someone as perfect as Nate never should have been with someone as annoying as Vanessa. #sorrynotsorry.

26. Serena & Aaron Rose
A little weird because Aaron is B’s new step brother but this relationship was uneventful, short lived, and easy to forget. Plus Serena always liked them a little weird anyway.

25. Nate & Bree Buckley
Rebelling against your parents and family by intentionally dating someone they wouldn’t approve of? How passé.

24. Jenny & Asher Hornsby
In the grand scheme of “Gossip Girl,” accidentally dating a gay falls pretty low on the interesting plot line chart.

23. Nate & Raina Thorpe
Sure, Raina was Nate’s best friend’s ex, but in the Upper East Side, that’s just a regular Tuesday. The only slightly ridiculous thing is why a career driven and focused woman like Raina would ever want to be with a no plan stoner like Nate.

22. Chuck & Raina Thorpe
Fucking your enemy’s daughter to get ahead? All in a day’s work for Chuck Bass.

21. Dan & Olivia Burke
Honestly, this whole relationship was just completely unrealistic. How the fuck was Dan and his unruly chest hair ever supposed to land a movie star like Olivia? And then convince her to threeway? Next please.

20. Nate & Lola Rhodes
The long lost Rhodes cousin. Or actually sister. Yep, Nate did the dirty with his first love’s secret half-sister.

19. Serena & Steven Spence
Sure, Steven was older and had a teenage daughter, but given S’s very severe and prominent daddy issues, this seems almost normal. But only almost.

18. Serena & Colin Forrester
Having an affair with your hot as hell college professor? I’d be lying if I said that wasn’t the only thing I wasn’t able to cross of off my undergraduate bucket list.

17. Jenny & Damien Dalgaard
Little J was only vaguely interesting when she was moonlighting as an UES drug dealer with her ridiculously hot older boyfriend. Who was also the son of a diplomat. #goals for anyone else? Just me? Cool.

16. Dan & Georgina Sparks
Homegirl defines crazy. Enough said.

15. Serena & Carter Baizen
Another blip in the romantic life of SVDW. The blonde goddess that was Serena needed Carter to help her find her long lost father and then later played poker to win his freedom? Sure, that seems realistic.

14. Dan & Rachel Carr
How redundant the teacher/student affair would come to be. This one was only vaguely fucked up considering the Blair drama and that Dan was still in high school.

13. Blair & Louis Grimaldi
B ending up with a prince? HAHAHAHAHA.

12. Serena & Tripp Vanderbilt
Having an affair with a married man is bad. Having an affair with a public officer is worse, scandal wise. Having an affair with a political figure and him leaving alone post car wreck? That’s all kinds of fucked.

11. Chuck & Eva Coupeau
Falling in love with someone when they don’t even know your real name and after they cleaned your gunshot wound? What is this, a James Bond movie?

10. Blair & Marcus Beaton
I think it’s time to admit you’ve hit rock bottom when your boyfriend cheats on you with his step-mom.

9. Nate & Catherine Beaton
Again, if the person you’re dating is cheating on you with someone in their own family, it’s time to reevaluate your life. This is only worse because when Nate and Catherine were together, she was married. To the father of the other man she was sleeping with. I think someone needs a therapist.

8. Blair & Dan
He was your best friend’s first great (and only) love and he just wrote a book chronicling all the internal drama in your friend group. And you were married to a prince at the time. Do better, Blair. Please just do better.

7. Serena & Gabriel Edwards
If only Serena wasn’t so desperately searching for love in all the wrong places, maybe then she wouldn’t have fallen for a con artist who tried to rob her family and friends out of millions of dollars.

6. Nate & Sage Spence
How was this not a bigger issue when the show was on. Sage was in [i[high school. She was a fucking minor. Nate had to have been around 22 or 23. That shit is creepy and wrong and borderline illegal. No. Just no.

5. Nate & Juliet Sharpe
Nate was dating a girl who conned herself into his and his friends’ lives in order to stalk Serena and ruin her life because ‘she’ was the one to put Juliet’s brother in jail back in high school. Wait, you’re saying the exact same scenario didn’t happen to you too your freshman year of college? Weird.

4. Serena & Ben Donovan
I think it’s time to admit that if your mom perjures herself in order to send an innocent man to prison on statutory rape charges and then he plots to ruin your life in tandem with his sister behind bars, this probably isn’t the most healthy relationship. Serena needs a good psychiatrist, not a boyfriend.

3. Nate & Diana Payne
Is Diana your best friend’s supposedly dead mom? Is she a madam of a high end prostitution ring who goes by the name of India? Did she help fake the death of the father of the child who she may or may not be the mother of? Did she conspire with your grandfather to get you a job at a paper and build up your professional credibility? Are all of these semi true when it comes to Nate and Diana? Yep, seems like a foundation for a lasting and trusting relationship.

2. Serena & Dan
Serena and Dan are step-siblings who share a half-brother. Any way you slice it, that’s fucked up and borderline incestual. Couple that with Dan being Gossip Girl (still one of the worst ending to any TV show, ever), the online anynomous blogger who ruined their lives for years as well as all the backstory between the S and D and I think there is a pretty solid argument to be made for diagnosing the two of them as clinically insane.

1. Blair & Chuck
If Blair and Chuck are your #relationshipgoals then you are wrong and need help. It’s a masochist coupled with a narcissist who hurt each other in truly terrible and innovative ways. This is not something to aspire to, but rather an example of a toxic relationship with heavy doses of mental abuse on both sides. This relationship is so incredibly fucked up that it is physically painful when they end up together.

Email this to a friend


Champagne Showers is a contributing writer for TSM. She is your typical Northern Diva. If curse words, sexual content, and drug use offend you, then bless your heart. CS will continue living the life you're too scared to live. email her at:

For More Photos and Videos

Latest podcasts

New Stories

Load More