The character of Serena van der Woodsen was played by the beautiful and talented Blake Lively. Throughout the course of Gossip Girl, Serena van der Woodsen dated plenty of guys but ultimately, she ended up with the person who was right for her. In other words, she had to kiss a lot of frogs before she was able to find her prince! The funny thing is, she found her prince earlier on in the show but still dated around before coming to that realization.
The character of Blair Waldorf is played by the amazing and unforgettable Leighton Meester. Over six seasons of Gossip Girl, We watched the character of Blair Waldorf date a handful of guys that she found to be very interesting. Some of them were way below her level but one of them ended up being the person that she knew she wanted to be with for the rest of her life!
Continue reading to find out how we ranked all of Serena and Blair’s relationships throughout the entire Gossip Girl series.
15 Serena And Gabriel Edwards
Serena and Gabriel top our charts for being the worst couple in Gossip Girl. Serena dated plenty of men but he was the worst. The reason we feel this way is because their entire relationship was a sham. Gabriel only showed interest in Serena because he was trying to financially con her and her family out of their money. He was absolutely despicable.
14 Blair And Louis Grimaldi
Blair and Louis were never meant to be together and the fact that they actually ended up getting married was a seriously tragic storyline in Gossip Girl. On their wedding day, Louis found out Blair still loved Chuck so he threatened her and basically told her that she would be trapped in a loveless marriage with him! She ended up running away.
13 Serena And Colin Forrester
Serena and Colin Forrester weren’t a great couple, simply due to the fact that he was one of her college professors. Their relationship was totally inappropriate and uncalled for. She put her academic career at risk and he put his career as a professor at risk when they chose to engage in a relationship.
12 Blair And Jack Bass
Blair and Jack Bass we never technically a couple, but they did sleep together. The fact that Blair slept with Jack doesn’t make any sense because it is totally out of character for her. Jack is one of the slimiest characters in the entire show. He doesn’t have Chuck’s back and he tried to assault Lily van der Woodsen at one point!
11 Serena And Tripp Van Der Bilt
Tripp left Serena's battered body in a crashed vehicle on the side of the road. Need we say more? He crashed his car and then left her in the driver’s seat to make it look like it was her fault. It is super disturbing that he was willing to stoop to such a low level to cover his own reputation. It shows us that he never really cared for her at all.
10 Blair And Carter Baizen
Blair and Carter were never a good match and the fact that they had a little bit of a fling is super creepy! They had no business getting involved with each other because he didn’t have her best interest at heart. Their relationship made Chuck feel super unhappy and uneasy. He did, on the other hand, date Serena for a bit and he truly cared for her.
9 Serena And Steven Spence
Serena and Steven are another couple from Gossip Girl that we don’t really respect or support. The reason why they weren’t the best couple ever is that she lied about her entire identity to enter into the relationship with him. If you can’t be yourself with someone, there is no point in being with that person at all!
8 Blair And Marcus Beaton
Blair and Marcus Beaton are another terrible couple that we saw on Gossip Girl. The way their relationship unfolded was super uncomfortable for everyone around because he was secretly having an affair with his father's wife… His stepmother! How twisted is that? He was using Blair as a cover-up.
7 Serena And Aaron Rose
Serena and Aaron weren’t a great couple on Gossip Girl either because Serena realized that Aaron was not a one-woman type of guy. He was the type of guy who liked to date around and hook-up with multiple girls at one time. Serena was the type of girl who liked to be the center of attention with whichever guy she was dating... Aaron couldn't do that for her.
6 Serena And Ben Donovan
Serena and Ben Donovan were somewhat of a likable couple because they got together after finding out the truth about what happened when she was at boarding school. She understood that her own mother had put him through so much turmoil and pain (and prison time) and he looked past all of that and tried things out in a relationship with her.
5 Blair And Dan
Blair and Dan were somewhat of a likable couple because they went from being two people that couldn’t stand to be around each other at all, to having serious romantic feelings for each other. It was super unexpected and out of the blue for them to become a couple but it was also very interesting to watch unfold.
4 Serena And Nate
Serena and Nate were a somewhat likable couple because they were always good friends to each other. On top of that, Nate actually swiped his V-card with Serena so there was an undeniable connection and bond that he felt with her. Relationships that blossom from friendships are usually the strongest, and even though this one didn't work out, they were still able to remain friends.
3 Blair And Nate
Another somewhat likable couple would be Blair and Nate. Their relationship ended earlier on at the beginning of the show series, but when they started out, Blair was madly in love with Nate! She envisioned a beautiful and bright future for herself and Nate, far beyond high school and far beyond senior prom.
2 Serena And Dan
One of the most amazing couples on Gossip Girl would obviously have to be Serena and Dan. They had an off-and-on relationship throughout high school and they dated other people a lot of the time. But ultimately, it was clear to everyone that they were meant to be together. Seriously, we all knew that they were going to end up together.
1 Blair And Chuck
The most amazing couple of all, when it comes to Gossip Girl, would have to be Blair and Chuck. They definitely take the crown. Their relationship was so intense, intriguing, and majestic. The love that they felt for each other was undeniable and incomparable to any other relationship in the entire TV series. They certainly had their problems but their relationship was and is unforgettable.
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