One of the things I love most about Gossip Girl is the slew of random characters whose sole purpose is to keep the plot interesting by shaking things up for our favorite four Upper East Siders and two annoying Brooklynites who endlessly complain about their unfortunate financial lot in life from their gigantic loft in one of New York’s most expensive neighborhoods. I digress. Anyway, as with any television show, each season introduces a few new characters, some of whom are truly perfect temporary additions to the cast, like
Fleur Delacour Eva Coupeau, and others are less than perfect, like most of the writers’ choices.
I’m a loyal GG lover, so I typically hold back when it comes to some of the laughable wardrobe choices, but as I rewatch this scripted trash for the ninth time, I can’t bite my tongue about the most egregious part of this show: the randos. Without further ado, I give you the worst and/or most annoying random characters who we all love to hate. Enjoy.
For those of you who forgot who she is, allow me to remind you. She’s the sister of the boarding school teacher-turned-convicted-felon with whom Serena allegedly had an affair when she was 15 and he was…older than 15. Mhmm, makes sense. Anyway, if I had to pick the worst thing about Juliet, it would have to be the way she dresses. Literally, all of her outfits are different yet heinous versions of the same business-professional dress with a cropped blazer over it. Like???? When I was in college, I literally wore jeans and sweaters every goddamn day.
Aside from her sartorial errors. her character is also incredibly creepy. I’m pretty sure the most disturbing exchange in this entire series is one that took place between Juliet and her brother during a prison visit when she says, “Keep your focus on not getting raped or killed” to which he responds, “It’s a minimum security prison” and she counters with, “And you’re hot” and then they seductively hold hands across the table and exchange minxy smiles. I think it’s totally okay to say he’s handsome or attractive because, criminal or not, he is both of those things, but hot? That’s your BROTHER. Why don’t you go take a cold shower, sis! Also, her whole purpose on this show is to, like, physically injure Serena and get her expelled from college, which is pretty shameful. Even Georgina would disapprove of this.
Damien has a lot of unfortunate qualities that earned him a spot on this list, but the one thing I truly couldn’t stand was how condescending he was to Jenny while they were dating. When they were about to have sex, she was really nervous because she was a virgin and he was like, “I get it. I’m older than you and when I date someone, sex is a a big part of the relationship. You’re a young, innocent girl, so I get that you’re nervous.” He was in Serena’s class at boarding school, which would make him no more than two years older than Jenny, so I’m confused as to why he’s talking to her like a World War II veteran who’s seen more than she ever will.
Acting like a cultured citizen of the world was like, his whole persona, which I just found incredibly annoying because he was literally 18 at the time, so no one’s buying it, sweetie.
This is another character whose circumstances really confused me. My knowledge of British monarchy is based solely on The Crown, so forgive me if I’m wrong, but if Catherine were a “lady,” that would mean she’s married to a duke, which we’ve been told she is. So if that’s the case, why would they be summering in the Hamptons and living in a townhouse in Manhattan the rest of the time? Don’t they have royal duties in England to carry out? Don’t forget, this was pre-Meghan Markle.
The second, and slightly bigger, issue with this lady is that she has a title of nobility and yet she’s paying an underage American kid to bang her against her dryer every few days. Two felonies for the price of one! How did this affair even work? Would she text him on her burner cell and be like, “Hey, when you’re done with algebra, can you come over?” Let us not forget, she was also f*cking her stepson. Safe to say, this woman needs therapy.
I know she’s not technically considered random since she’s in every season, but she’s not part of the main six, so to me, she’s a random. Sorry (not really) to all of the Vanessa die-hards, but she plainly sucks. She’s one of those people who feels way too comfortable around people she just met and, maybe it’s just me because I still don’t feel comfortable around people I’ve known my whole life, but that’s not a likable quality. Second, I didn’t like how she was always at private events for schools she didn’t attend! Like, she was at literally every dance, party, and study session of the Constance girls and then at the Columbia alumni events. Seriously, she doesn’t even go here!
Okay, to set the record straight, I hated the fake Charlie Rhodes (Ivy Dickens), but lived for the real Lola Rhodes. I know this isn’t a character flaw, but there was something about her voice that made it really hard to get on board with anything she was talking about, and her pretending to have a mental illness to explain her behavior wasn’t cool.
I know she was an actress being paid by the real Lola Rhodes’ mom to pretend to be her (happens all the time), but couldn’t Ivy have just, like, gotten another acting job that didn’t involve fraud? I can’t imagine being so desperate for a job that I’d hear Carol’s pitch and think it was a good idea.
Sorry, but Tripp and his waspy-ass name was a giant p*ssy. Like, literally everything about him was so pathetic and sad—especially when he crashed his car and put Serena in the driver’s seat to make it seem like it was her fault. Why do all of these people in positions of power take no more than two seconds to consider whether or not they want to commit a crime? I take more time deciding between two identical pale pink nail polishes than Tripp did to pin a car crash on his mistress. I also feel like Nate’s fancy politico cousin should have been 10 times hotter than Tripp, who looks like he calls his mom four times a day. I definitely wouldn’t have voted for him.
Hands down Serena’s least likable boy toy. His skinny scarves and confusing haircut were enough for me to decide he sucks, but then he opened his mouth and…it didn’t help his cause. Like Damien with Jenny, Aaron acts like Serena is just a young and stupid child who doesn’t understand the complexities of adulthood, which is hilarious to me because Blake Lively was 22 playing a 17-year-old, but whatever. Anyway, even if that is the case, you are fully aware that she’s in high school, so stop acting like her being young is a flaw you have to get past! He should be more concerned with the statutory rape he’s committing.
Also, his whole “I date multiple women at once” thing is just gross. I understand that you can’t expect monogamy after knowing each other for approximately five minutes, but Aaron, you don’t need to constantly remind her that you’re f*cking 10 other women at the moment. All in all, he was not hot enough to act that smug and condescending, and I was truly elated when Serena told
us Dan that she left in him in Argentina.
And there you have it, the worst random characters in Gossip Girl! Did I leave any out? Let me know who you hated the most in the comments! Until next time, Upper East Siders. XOXO, Gossip Girl.
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People who are way too vocal about how a TV show or movie is nothing like the novels they’re based on are the absolute woooooooorst. And in case you haven’t noticed, I am the absolute woooooooorst, especially when it comes to my taste in TV shows, according to our comment section. Gotta be honest, I watched only binge watched Gossip Girl once, and once was all I needed. However, I work at Betches, so I’ve seen enough content to act like I’ve seen the show a thousand times. I used to read the books religiously when I was in middle school, so I’m expert here (kind of) on the differences between the books and the show. So I can say with confidence that some of the changes Josh Schwartz made to 11-year-old Millie’s beloved Gossip Girl franchise suck more than when he killed off Marissa on The O.C. or brought on Taylor and Oliver. Here’s the lowdown on the worst of the worst amendments made to the Gossip Girl TV show.
Almost Everything About Chuck
The only similarities between book Chuck and TV show Chuck are that he’s super loaded, he was involved with Blair, and I cannot believe he’s in high school. Both of those Chucks never had to worry about typical high school things like grades or getting random boners during class (feel like Nate in both settings would have to worry about the latter, though). But first off: Chuck in the novels barely dated Blair, and it happened for only a year when they were in Oxford together. He did assault Jenny in the novel and the show, and shame on CW for being so forgiving and romanticizing him after that. (Maybe Ed Westwick is hoping he’ll get the same treatment TV Chuck Bass did after getting #MeToo’d, and that’s probably gonna happen to because he’s a privileged white male.)
In the novel, people really didn’t like him to begin with and he was only allowed in the social scene because he’s rich. But as the series went on, it was alluded to that Chuck was bisexual. Chuck also got rejected from every college because his parents didn’t love him enough to participate in Operation Varsity Blues. He was forced to go to military school by his dad, but he never showed face to orientation or classes. Overall, the biggest difference between novel Chuck and TV Chuck is that TV Chuck was portraying as a brooding, smoldering dude, whereas novel Chuck was just an asshole with little to no redeeming qualities. I cannot tell you how many times I’ve seen girls post sappy photos of Chuck and Blair on social media, saying, “I want a Chuck to my Blair!” No! Why are we romanticizing TV Chuck? He’s totally the type of guy to ask for nudes before you go on a date or texting “making it move” in response to something that wasn’t remotely sexual. Being the friendless, rudderless guy with no real friends is what Chuck deserves, and I’m glad the novel put him in his place (until his random romance with Blair).
Everything About Jenny
TV show Jenny is blonde, lithe, and eventually, very edgy. Novel Jenny was really short, had brown curly hair, and had really big boobs. Book Jenny had a one-sided fling with Nate where she made googley eyes at everything about him and he just made googley eyes at her huge rack. They hooked up with him in Central Park and someone filmed it. The relationship ended because Nate is SUCH a boy. Ugh, typical. After getting expelled from Constance for partying, Novel Jenny eventually went off to boarding school, where she went from underdog to being pretty popular (and inspiring a v good spin-off book series, The It Girl).
TV show Jenny, meanwhile, bitched out and left because Blair banned her from Manhattan. As I get older and older, this city seems to get smaller and smaller, and I bump into random people I know at least three times a week. So yeah, I’d wanna ban someone I hate from this city too because I don’t want to see their face. But WTF kind of prick has the audacity to ban someone from a city? Are you the police? No? Then you can’t tell me where to live. And furthermore, what kind of loser is like, “K, I’ll leave because you, some person who has no power over how I live my life, say so”? That’s such a weak exit on the writers’ end for one of the only characters I actually liked. The books did Jenny way more justice by showing us her downward spiral riddled with illicit drugs and rockstars, only to be expelled and sent off to boarding school.
Everything About Dan
The worst change that was made to Dan is that he was Gossip Girl the entire time. And then what’s up with the writers being like, “Okay, the characters can be miffed but Dan is welcomed with open arms five minutes later.” That sh*t doesn’t make sense. His relationships on the show were almost as terrible as him running a blog so stalkerish it would put Joe Goldberg from You to shame. Serena and Dan dated very briefly in the books, but broke up when they realized their relationship has zero depth. In the TV series, they break up a bunch but end up getting married in spite of their entire relationship consisting of gossiping about drama, creating drama themselves, and having extended eye contact as music swells in the background. That kind of relationship ultimately has no depth either, but was way more torturous to be drawn out for years. Novel Blair and novel Dan hate each other or don’t even acknowledge each other the entire time. TV Dan and Blair hated each other initially but ended up having like, the healthiest relationship on the show. Why didn’t they end up together again? Novel Dan’s biggest relationship was his on-again-off-again relationship with his bestie Vanessa (who shaved her head bald in that world). In the TV show, he just dates Vanessa very briefly after a threesome with Lizzie McGuire and they decide they’re better off as friends.
TL;DR Everything about Dan sucked in the series because it just made him have as much depth as a martini glass. Novel Dan at least had redeeming qualities and—get this—had some character development.
The Blair-Serena-Nate Love Triangle
The TV series just made it seemed like Nate was riding a merry-go-round of hookups and high school romances with zero depth. He did date Serena and Blair, but neither of those relationships were as profound as the girls’ other relationships. They didn’t even give him a happy ending by giving him a soulmate, which is honestly the most realistic part of the show because literally 95% of 30-something-year-old NYC guys don’t find someone they’re going to spend the rest of their lives with. Shout-out to Josh Schwartz for being realistic for one time in any of his TV shows!
But novel Nate actually did volley between Serena and Blair throughout the entire book series because he was in love with both of them, and had a couple of hookups in between. He didn’t want to get in the way of their friendship and so he sailed around the world with a family friend. Again, this is totally realistic because guys will do anything to avoid confrontation and dealing with their issues. So, in both different instances, he’s a typical boy, but his love triangle with Blair and Serena was way better than Blair and Serena having sh*tty relationships with Chuck and Dan. I was more emotionally invested in the love triangle because they all genuinely seemed to love each other, and it was hard to see how that relationship would’ve worked itself out, which makes it juicier.
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