Ranking 30 Of My Favorite And Least Favorite Gossip Girl Couples From Horrible To Adorable

I've watched Gossip Girl four times and counting, so I thought I would give my ranking of my least favorite to my favorite couples. Were Blair and Chuck a match made in Heaven, or should they have called it quits long ago? **SPOILERS**

30. Jenny and Asher

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Jenny and Asher weren't a good couple. Jenny was only dating Asher so that people would think she was "super cool" because she had a hot boyfriend, when in reality it all came crashing down.

29. Rufus and Ivy

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Ok, really with this one? Ivy was a 19 year old pretending to be Lily's niece. She was basically the same age as his actual kids, not to mention Dan kissed Ivy on several occasions.

28. Serena and Ben

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This one I don't get. Ben had thought that Serena sent him to jail, and he had been plotting his revenge for years, but when that time comes around they end up together? After he had been accused of being with a minor(Serena)? This relationship made no sense im my opinion

27. Chuck and Jenny/Vanessa

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Both of these "relationships" were stupid and not needed in my opinion. It was mostly Chuck's fault for sleeping with Jenny, but then Blair got mad at Jenny when it was only partially her fault. I feel like Chuck had already grown so much as a character, that him sleeping with Jenny back tracked all his progress by a lot. Him and Vanessa were just stupid.

26. Eric and Damien

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Honestly, I don't know if Damien was gay, but they were not a good match. Friends or not, Damien was a bad influence on Eric and had him doing a lot of bad things.

25. Jenny and Damien

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This was equally as bad as Eric and Damien. Damien had Jenny as her drug mule and he also kept trying to get her to sleep with him, even though she wasn't ready.

24. Eric and Asher

Ok, they weren't even really a couple. They only kissed a few times, but I feel like the whole purpose of them was to put a divide in between Eric and Jenny since they had both been with Asher.

23. Blair and Dan

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This coupling makes no sense. Blair had made it a point for most of the show that she wanted nothing to do with Dan. She didn't even want to be seen with them when they hung out, or when they were dating for a while. Dan was always jealous of her and Chuck and that interfered with their relationship.

22. Serena and Tripp

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Serena and Tripp were cute together, but Tripp was an absolute dick. First, he cheats on his wife to be with some teenager/young adult who was known for sleeping around. Then when they go on vacation together, he lies to her and leaves for the entire day. Then, when he does return and drives her home, when they get into an accident, he just leaves her? What an absolute idiot.

21. Nate and Diana/Catherine

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Nate was such a sweet guy, and then he goes and sleeps with this woman just so his family will have some money. Diana ended up using him as her "stud" and she never took him seriously while he was working for her. Not to mention the fact that Diana was Chuck's fake mother/ working with Nate's grandfather/ helping hide Chuck's dad whilst running a sex club. Catherine and Nate were just wrong, especially when Catherines step-son, who was also sleeping with Catherine, was dating Blair.

20. Dan and Georgina

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I'm not gonna lie, they were pretty cute together. Georgina did pretend to have Dan's kid and make him help raise it. The main problem was that Georgina brought out the bad side in Dan and she helped him write his expose on his friends. Also, don't forget the fact that she made up a pretend person to become friends with Dan to split up him and Serena.

19. Lily and Bart

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They were both manipulative and controlling, so I feel like they were a good match. Although, Lily did cheat on Bart the night before their wedding with Rufus. After Bart came back from the dead, he was way more controlling and evil towards Lily then before.

18. Blair and Louis

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OK, at first it was Blair's fairytale dream, then, Blair just kept talking to Chuck and Louis got super mad and defensive, so Louis did a lot of really bad things. The worst being when he told Blair on their wedding night that their whole wedding was just an act and that she belonged to him basically.

17. Lily and Rufus

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Lily and Rufus would've been a good match, if Rufus had actually put some effort into their marriage. He just walked around acting like he didn't belong, when he put absolutely no effort into trying to belong and not going to the events that Lily was going to. If he would've stopped acting like he didn't belong, then he probably would've fit in.

16. Serena and Steven

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What is it with people on the show dating people that are either way way younger than them, or old enough to be their parents. The fact that Steven had a daughter almost the same age as Serena, and that that same daughter was also dating Nate who is the same ages Serena was just messed up. They were pretty cute couple, but they would not have lasted especially since they met when Serena was going by a different name.

15. Nate and Serena

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Nate was definitely way too good for Serena, and Serena constantly took him for granted by making him go through her deciding whether she liked him or Dan. Also, the way they got together was just not OK. The fact that she slept with Nate while Blair and Nate were still dating was also not ok. Sure they were drunk, but its still their fault.

14. Nate and Jenny

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Nate and Jenny were super cute together, and I wish the riders would have explored their feelings for eachother more. Sure it was kind of awkward with Nate and Dan being close friends, but they were adorable. Jenny definitely did not deserve Nate though. Nate kept coming to the rescue Jenny, and all she did was rebel.

13. Dan and Olivia

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Dan and Olivia were cute together, but Dan should have been more honest about his feelings for Vanessa. Also, the whole threesome thing was a stupid mistake on their part and basically destroyed their relationship. Also, the fact that they were able to get Hillary duff to play on Gossip Girl was pretty cool.

12. Lily and William

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Lily and WIlliam were OK together. Sure, William gave Lily's mom fake cancer, and sure he also dated Lily's supposed niece, but he obviously wanted her back. The thing that bothered me the most was how Lola was also his daughter and the fact that he just left Serena after she had finally reconnected with her father. He could have been a bit nicer with Rufus since he had taken on the role of father after William left. They were cute nonetheless and gave Serena and Eric a glance back at their childhood.

11. Dan and Serena

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I know people have mixed opinions about this one, but really? He created a blog stalking her and making her out to be some villain, but yet she marries him? Serena calls what Dan had been doing a "love letter to her". Seriously girl, come on, he wrote an expose on you and your friends and ran a blog bullying and harassing all of you, and you call that a love letter? The reason this isn't ranked super low is that I feel like they are the best match for each other. Serena has done her fair share of bad things as well, but I feel like they bring a balance to each other.

10. Blair and Nate

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Maybe they were only dating because their parents wanted them to or because they were familiar. They were a cute couple together, sure Blair did some bad things when they were first dating, but they were a cute high school couple. They ended up to be good friends too, which was nice.

9. Dan and Vanessa

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I feel like they were a good match for each other because they were both manipulative and pretended to be the "good person". Vanessa always acted like if she did something bad to Serena or Blair, then "they deserved it", but no one ever stuck it to her. They mostly were friends with benefits, but their relationship was not the worst of them. Vanessa was very insecure while they were dating.

8. Chuck and Raina

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Chuck and Raina were from similar families and I think that made them go well together. They both knew what it was like to have business minded parents. It was sad that Chuck used her at first to get his company back, but then I think he actually liked her. Blair also did not help his case at all. If they really tried, I think they could have had a good shot

7. Nate and Vanessa

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Honestly, I think they were pretty cute together. Her feud with Jenny, however was not cute. They should have acted grown up about their feelings and Jenny should have just let Vanessa have him and see how they worked out. If they hadn't been so focused on revenge, I think they could've worked out great.

6. Nate and Sage

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Honestly, their relationship was super cute. Had she not been a minor, then it would have been ranked higher. Yes, she was sort of petty, but they were great together. The age was somewhat problematic, but they liked each other and helped each other out.

5. Chuck and Eva

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I think Chuck and Eva's relationship was beautiful. Eva was obviously a kind and loving woman to have taken care of Chuck when she didn't even know who she was or why he was injured. They would have worked better if Chuck didn't believe Blair over his girlfriend, Eva. Overall I don't think they would have lasted long-term unless Chuck worked on himself a bit and trusted Eva more.

4. Eric and Jonathan

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Eric and Jonathan were so good together. Sure, they had their ups and their downs, but so does everyone. Bart was one of the main problems in their relationship in my opinion, since he was constantly manipulating Eric. Also, If Jonathat hadn't cheated on Eric, I think they may have lasted, at least for a bit.

3. Serena and Carter

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Serena and Carter were super cute together, but I do think Serena took advantage of him and didn't appreciate him enough. Carter literally was willing to work in a labor farm for Serena. The fact that Carter also went all over the world with Serena in search of her dad must of meant that he really cared for her.

2. Blair and Chuck

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OK, hate me all you want, but Blair and Chuck were super good together. Yes, they both did horrendous things to each other, but they also grew so much together. The fact that they didn't get back together until after they had their lives situated really shows how much the grew because they knew if they got back together it would be their last shot, so they wanted to make sure they were ready. I think that Chuck's story is incredible and he grew so much as a character. Yes, he tried to sell Blair for a hotel, but he also grew. I love how Blair made Chuck a better person, and actually got him to fall in love. There's multiple occasions where I was kicking myself when they either had a misunderstanding or a missed opportunity.

1. Cyrus and Eleanor

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Cyrus and Eleanor were the best couple on the show altogether. They were so kind and Cyrus was such a great father figure in Blair's life. Even though at first Blair didn't like him, I think he really grew on her. Eleanor could be quite rude to Blair, but I think Cyrus really brought out the best of her. I love the fact that they were basically together for the entirety of the show, which is something that I don't think any other couple had . Overall, my favorite couple on the show.