When it comes to entertaining television, Gossip Girl definitely takes the cake! It is one of the best shows from the early 2000s and it is still easily binge-watched today. The technology might seem a bit out of date with their flip phones and everything, but that truly doesn’t take away from how amazing the show is!

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The show focuses on the lives of Serena van der Woodsen, Blair Waldorf, and Dan Humphrey. They start off as high school students who are just trying to figure out friendships, relationships, and going to college in the future. The show continues to progress beyond their high school graduation. The mystery of who Gossip Girl is is constantly being questioned by the characters of the show and they don’t find out until the end! Here is a list of Dan Humphrey’s love interest, ranked from worst to best.

10 Worst: Rachel Carr, His High School Teacher

Dan Humphrey and Rachel Carr had no business getting together. First of all, he was an underage high school student and she was an adult woman in her 20s when they first hooked up. She knew exactly what she was doing was doing was wrong.

She gave into temptation because Dan Humphrey was one of the only students who was really kind to her at the high school in the midst of her getting bullied by Blair Waldorf... but that is still no excuse.

9 Worst: Georgina Sparks, Blair And Serena's Enemy

The relationship between Dan Humphrey and Georgina Sparks ranks as being one of the worst relationships he could’ve gotten into. First of all, Georgina Sparks is one of Blair and Serena’s biggest enemies throughout the course of the show. That alone should’ve kept Dan from getting involved with her.

Second of all, Georgina pretended to get pregnant by Dan Humphrey even though she knew that she was pregnant with someone else’s child.

8 Worst: Alessandra Steele, The Shady Publicist

Alessandra Steele and Dan Humphrey never actually hooked up but the flirtations were initially there… Until she messed up by hooking up with Chuck Bass who was literally only trying to use her for his own selfish benefits.

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Every time Alessandra realized she needed to do her job as a publicist and take care of Dan’s future publication, she jumped to it. The fact that she actually cared about Dan’s book is what makes her slightly redeemable but for the most part, she was not a great character and it is probably a good thing for Dan that he never actually hooked up with her.

7 Worst: Ivy Dickens Was Unstable

Ivy Dickens ranks at being one of Dan Humphrey’s worst romantic interests in Gossip Girl because she was mentally unstable. She was a hired actress who entered into the lives of the Van der Woodsen family for a paycheck.

Once she was living a life of wealth and luxury, she stopped taking her medication and started acting out in a way that made everyone question her sanity. At one point when she was hooking up with Dan, she asked him to call her Serena which was really creepy and weird.

6 Worst: Amanda Lasher, Hired By Chuck To Date Dan

Amanda Lasher is definitely one of Dan Humphrey’s worst romantic interests on Gossip Girl. She never actually was interested in him for who he was as a person. She was hired by Chuck Bass to pretend that she had a crush on him in order for Chuck to maintain power and control over a situation.

She ended up getting her hair burned off by Blair’s minions in a nightclub so she sort of got what she deserved. Dan Humphrey should have taken more time to get to know her before starting to date her. She wasn’t actually into him at all.

5 Not So Bad: Blair Waldorf Hated Him For Years But He Adored Her

Dan Humphrey’s relationship with Blair Waldorf, played by Leighton Meester, wasn’t all that bad even though it seemed very peculiar at the time. Blair Waldorf hated him for years and never thought he was good enough for Serena yet she personally decided that he was good enough to become her own boyfriend.

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It is probably based on the fact that he was emotionally there for her in quite a few occasions and the fact that he adored her so much that he wrote about her in such a positive and uplifting way in his book. The relationship between Dan and Blair broke girl code in every way because Blair should’ve been more concerned about her friendship with Serena. Ultimately, everyone was happy to see Blair with Chuck in the end.

4 Not So Bad: Willa Weinstein, The College Girl

Dan Humphrey’s relationship with Willow Weinstein wasn’t so bad. She was a college girl who did quite a bit of meddling when it came to his and Vanessa Abrams' book publication… Other than that, Willow wasn’t that horrible of a person.

She just really wanted to show Dan that she was down for him and that she would do whatever it took to take care of him. Her father was connected in high places and had a lot of power and she was able to contact her father to try & help Dan with his future. He is the one who lost interest in her.

3 Not So Bad: Olivia Burke, The Gorgeous Actress

Dan Humphrey and Olivia Burke had a really great relationship! He didn’t know that she was a famous actress when he first met so he didn’t treat her like she was on a pedestal. She felt like she was a normal girl when she was with him and that is exactly what she was seeking.

They had a great connection… The only thing they got in the way was the fact that he still had feelings for Vanessa and those feelings were taking over his heart. If Vanessa had never been in the picture, Dan and Olivia might have had a great long-term relationship. She was played by Hilary Duff.

2 Not So Bad: Vanessa Abrams Since They Were Best Friends For Years

Dan’s relationship with Vanessa Abrams wasn’t that bad because they were friends for years! It was kind of obvious to viewers that a relationship between Dan and Vanessa was going to happen at some point. They grew up together and were always very close.

The fact that they had a strong friendship before entering into a romantic relationship gave them a good foundation. Unfortunately, they ended up realizing that they were better off as friends than romantic partners and they decided to part ways.

1 Best: Serena Van Der Woodsen, His Dream Girl

The best relationship Dan Humphrey had over the course of Gossip Girl was obviously his relationship with Serena van der Woodsen. She was played by Blake Lively. They ended up getting married which is proof enough that they loved each other hard for years, even though they dated off-and-on and other people in between.

The scene where they get married at the end of the show is super sweet and romantic! It let viewers know that even though Dan Humphrey was Gossip Girl the entire time, Serena had it in her heart to forgive him and keep loving him anyway.

NEXT: Here’s What Blake Lively Has Been Up To Since Gossip Girl