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We Ranked All Of Chuck's Sexcapades (And A Few Relationships) In Gossip Girl

Most of the people on this list were more flings, one night stands, and sexual endeavors, but there are a few actual relationships, like Eva Coupeau and Blair Waldorf. Some swoon worthy, some vomit worthy, and some that we've completely forgotten, to tell the truth.

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8. Jenny Humphrey

Giovanni Rufino, "Dan de Fleurette" Pictured: Taylor Momsen as Jenny, Ed Westwick as Chuck Photo Credit: Giovanni Rufino / The CW © 2009 The CW Network, LLC. All Rights Reserved. / Via–Jenny_relationship

Chuck did his fair share of awful things (and people, lets be honest here) during the six season run of Gossip Girl, but one of the worst was when he slept with Jenny. This one might even have been comparable to when he traded his girlfriend for a hotel. Sure, he and Blair weren't exactly together at the time, but still. And she was also Dan's little sister, and his step-sister (Lily married Bart, so he was Lily's step-son, Bart widowed Lily, Lily married Rufus, so Chuck was Rufus' step-son, and therefore, he was also the step-brother to Jenny.) There are a lot of effed up things happening in this show, but this one might just take the cake, or at least come close.

7. Amelia

Gossip Girl, The CW / Via

Chuck stooped pretty low with this one, too. Although nobody can be one hundred percent sure, its assumed that Chuck had a one night stand with Amelia, a girl employed by his father, after a falling out with Blair.

6. Alessandra Steele

Instagram @ig.ggconfession / Via

First things first, we are not rewriting 50 Shades of Grey with Ed Westwick/Chuck Bass as Christian Grey; its Alessandra, not Anastasia.

Honestly, I don't think anyone knew how or why this relationship happened. Dan's publicist dating Chuck? Probably one of the most unexpected relationships on the entire show (after Steven Spence and Lily, of course). But at least this one wasn't too dramatic.

5. Josh Ellis

Gossip Girl, The CW / Via

Who doesn't remember the time that Chuck and Blair were playing their "game" and Blair let Chuck kiss Josh Ellis, the admissions director, so that she could get into a school. This one was dramatic, explosive, but overall not a big deal. Compared to their other fights, this was just a small blip in Chuck and Blair's dramatic relationship.

4. Raina Thorpe

Gossip Girl, The CW / Via

Thankfully, Raina was actually one of Chuck's better love interests. She actually was quite like Blair; a strong minded, independent woman. Although her relationship with Chuck was full of many twists and turns - some funny, and some not - she came out as one of the best girlfriends he could have had. If it hadn't been for Nate's relationship with her and her father's involvement with Bart, she could have been runner up to Blair.

3. Vanessa Abrams

Gossip Girl, The CW

Vanessa just didn't fit in with Chuck's world, and there was no way Chuck was going to downgrade from his plentiful Upper East Side lifestyle for backpacking and Brooklyn to be with her. The relationship was not going to work out, no matter how hard the two of them tried. The best thing about this on-screen couple was that it led to a wonderful off-screen couple: Jessica Szhor and Ed Westwick!

2. Eva Coupeau

Gossip Girl, The CW / Via

Eva and Chuck's relationship was sweet, and one of the first times that viewers saw Chuck in a real, loving relationship. If it wasn't for the supremacy of the love between Blair and Chuck, this relationship could have definitely lasted. One thing it had that the majority of the relationships featured on the show lacked was a healthy dynamic.

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