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Holiday Revisit: Gossip Girl “Roman Holiday”

Kerensa worships Blair Waldorf and questions Dan Humphrey's writing talents with Emma Fraser and Whitney McIntosh

Holiday Revisit: Gossip Girl “Roman Holiday”

I’m joined by Emma Fraser and Whitney McIntosh to talk all things Gossip Girl—UES holidays, parental love triangles and the glory that is Blair Waldorf.

“Roman Holiday” picks up after Blair (Leighton Meester) has had her whatever-it-was with Chuck and gets back together with Nate (Chase Crawford) but she’s horrified that Nate will find out about her and Chuck (Ed Westwick). On top of that, it’s Christmas and Blair’s dad is back in town and our girl is obviously scheming to get him to stay in New York and if he conveniently left Roman…

Serena (Blake Lively) and Dan (Penn Badgley) are in love and super boring, so they decide to surprise each other with meaningful gifts which is obviously a struggle for Serena. There’s also some parental (Lily/Rufus/Alison/Bart) love triangle drama.

Kerensa: So I hate that this is how I'm opening our convo about "Roman Holiday" a Gossip Girl episode I loveeeee but....

I still can't get over Dan being GG because it literally makes the rest of the show, including THIS EPISODE, make no goddamn sense!

Whitney: You just haaaaaad to bring it up didn't you? Yes, it's true that eventual reveal makes the entire episode (and most episodes) fall apart at the seams, but it's still a classic and no amount of terrible plot decisions can change the magic of a Blair Waldorf plan coming together.

Emma: The only thing I'm sad about regarding this with this episode is there were no Dan reacts to things on Gossip Girl by himself scenes. But yeah it is a super fun episode with just the amount of drama, adult angst, schemes and side eye. I'd also forgotten what Taylor Momsen looked like pre eyeliner and every single terrible Vanessa outfit.

Kerensa: Vanessa has so many terrible outfits in this episode!

I mean, let's talk our girl Blair first though because duh. Watching Leighton Meester on this show always makes me so angry that she's not more famous. But Blair is particularly heartbreaking in this episode because she's dealing with the fallout from sleeping with Chuck--who is SUCH A SOCIOPATH. And she's trying to figure out how to get her dad back in NYC and she can't really accept that he's very much with Roman now. So, like Whitney said--enter classic Blair Waldorf plan!

Whitney: Vanessa's outfits are truly horrendous here. What makes it worse is that it comes off as the show incorrectly assuming that those types of over-accessorized and mismatched outfits are what a trendy hispanic Brooklynite would wear instead of, you know, dressing like most of the other characters in Brooklyn. Serena's outfits are pretty bad too though, what with the (not at all shocking) seasonal inappropriateness and unwrapping of presents in front of her mom's new boyfriend while in skimpy lingerie. Blair's outfits, obviously, are incredible from the cape/mock turtleneck/pearls skating combo to the A-line party dress and dramatic headband. She is perfect.

Blair's plan here is one of the better ones of the first season, mostly because it comes from a really true and human place rather than just a scheme to mess with people's lives because she finds it fun. She truly misses her dad and doesn't understand why he doesn't try to save face and be with his daughter more in New York. It's sad, and Blair's reaction makes her much less of a robot than she would become in later years. The music choices during their final two scenes together, Band of Horses and The Weepies, are very on point with this particular mood, and keeping with Gossip Girl's trend of picking very apt indie bands to highlight.

Emma: I honestly howled when I saw Serena's super slinky, sexy present opening attire especially as no one else batted an eyelid. I get that she might feel very comfortable with her body (which I'm all for) but considering how skeezed out she was when Lily mentioned Bart you would think she might change up her choice of morning clothing. Serena did wear one thing that felt appropriate for the time of year (shock horror) and that is the stripped knit dress AND she even has tights on. Bonus winter wardrobe points. Non one can beat Blair when it comes to perfectly picked out ensembles and the skating one as you mention is fantastic.

To the real star of the show and like you Kerensa I am so confused as to which Gossip Girl actress is the one on the cover of Vogue and in the public eye a whole lot more. This is the perfect showcase of who Blair is and her mother rightly puts it that she might seem like an adult, but deep down she is still a little girl. Blair needs to be grounded in this way to demonstrate why her scheming isn't just because she is a power hungry bitch and her father's departure has obviously had a huge impact. Her tricks are kind of way off and it doesn't take long for Eleanor to realize what her daughter is doing. Maybe because Blair gets her tricky ways from her mother (although I can't think of any devious Eleanor plans) she sees straight through it and recognizes this bratty reaction comes from a place of pain.

Music wise Gossip Girl is still one of my go to sources and right now because I sometimes like to go on the nose for what I'm listening to/writing about I have this epic Gossip Girl playlist on (it runs for 32 hours).

What do we all make of the Chuck subplot that runs through the episode? It's hard to remember how I felt about this Chuck storyline at the time over how I feel about this pairing now.

Kerensa: Oh man, I laughed so hard at Serena's Christmas present opening pajamas too! I legitimately think that people casually wearing lingerie like that only exists on television.

I love the relationship between Blair and Eleanor because beyond seeing how close they are you can totally see where Blair gets some of her tendencies from. I'm thinking in particular of the scene in Central Park where both Blair and Eleanor are sort of giving Roman the side eye, even though he's trying so hard. But they both can sense it and are very careful (and maybe rightfully so) in their treatment of him. Emma, I like that you bring up that Blair's bratty reaction comes from a place of pain because so true. I feel like so many of Blair's schemes on this show come from there too :(

Ugh, ugh, ugh Chuck. I think at the time was into it because DAIR (!) didn't exist yet but watching it now, like, Chuck Bass is such a fucking psycho. All his texts to B are so cryptic and awful and that last pic he sends her of him and Nate, ew ew ew ew.

Whitney: If I remember correctly, I was on board the Chuck/Blair ship back when it first came around, but only because Nate was so bland and Dair wasn't even a glint in the writers' eyes at that point. Chuck was much more "sexy mysterious" than "unabashed sociopath" for a short time in the beginning, so the pairing was intriguing instead of the blatantly unhealthy match it ended up being. The whole Monaco thing does come off as super creepy though. Only a glimpse of how twisted his blackmailing schemes were throughout their relationship.

All of the texting in this episode did give me a good laugh though, what with so many of the characters' "trendy" cell phones being Razrs or those ubiquitous Verizon flip keyboard monstrosities that were everywhere in the late-aughts. It's almost hard to take seriously how wealthy and flashy everyone was when they're carrying around those bricks and acting all smug when they send blurry cell phone pictures with an old school smile attached. I did love when Dorota gets a phone of her own for Christmas from Blair considering how much Dorota's texting contributes to the success or failure of so many schemes down the road. Dorota is the best.

Emma: Seeing which cell phones are on trend is one of my favorite things about watching teen shows from the 00s because it is the one thing that really dates it. I would actually find Dan far more believable as Gossip Girl if iPhones existed from the first episode because it would have been so much easier for him to post, but nope not with the phones they had. And the teeny tiny blurry shot is A+ Chuck skeeve. And it's such a great way to close out the episode.

Talking of shipping I'm pretty sure I was full on the Dan/Serena ship for at least the first two seasons. I am also weirdly swayed by couples when they're dating in real life for some reason so that might have added to this. Also they are both kind of smug about things (Serena's smug is oblivious to Dan's self-righteous smug) and that makes them perfect for each other. I hate to say it, but they're actually pretty adorable in this episode and I think the only reason why I'm giving their gift giving a cheese pass is because it's Christmas. However I can't excuse what feels like a fairly standard 'the first time sleeping together is magical' teen TV trope, this does not get the Christmas cheese pass. Am I right in thinking that this is Dan's first time?

Whitney: If I remember accurately, it was Dan's first time and they had that whole discussion about it a few episodes earlier when they almost had sex and he told Serena that. Or something. The gift giving is fine, but Dan turning down an expensive watch is so not believable. A middle class kid from Brooklyn turning down a $1000 or more watch? Worst case scenario he can hawk it when they break up. Poor planning there, Humphrey. Serena's smug face is so annoying, but mostly because that's the only face she makes besides her blank stare the entire series. I affectionately call it "Blake face" and it's probably one of the reasons I disliked Serena as a character so much after the first two seasons. Dan was clearly so much better than her as a person at this point that it always bothered me how much he worshipped her in their relationship.

Speaking of the gift giving, am I the only one who got irrationally angry when Dan gets published in The New Yorker when he is so clearly a mediocre writer at best? I don't care how much of a fantasy world these people are living in, but in no way shape or form does it make sense that a 17 year old could get published in The New Yorker with a story about how much of a crush he had on a girl when he was 15. It's more obvious that he can't really write worth a damn when his book gets published later on, but even here it's clear that he is not that creative. In my mind, Dan Humphrey is currently an editor for Vice who can't think of another original book pitch and still thinks his gelled hair is very hip. He's that certain kind of angsty 25 year old who acts like he is 45 and has more talent than everyone in the room. Serena probably got him the job as an apology for cheating on him shortly after their first anniversary trip to Zurich.

Kerensa: It was Dan's first time--and like I get that the whole snow thing was more of Serena's gift but she would be like "Merry Christmas you get to have sex with me!" The gift thing is cute but it also shows like how deeply Serena doesn't get it. The whole time I kept thinking Blair would have got Dan something amazing!

Whitney, I totally agree. And I don't think I can outdo that paragraph. But Dan Humphrey definitely works at Vice, for SURE. What kind of #hottakes do you think he's writing about?

Emma: The super cleavy sparkly dress Serena wears for her gift giving is another in the surprising tick column, but the way she pulls her strap down made me eye roll so much. I mean I like seeing the girl take control, but when accompanied by her half giggle thing it's just a bit too much to take.

Like you both I also found the whole The New Yorker gift from V beyond annoying and considering how much they harped on about him being this AMAZING writer Inside really wasn't all that (although I would love to read it). I definitely think Dan would be writing about how over Brooklyn is and I can see him wanting to move Upstate so he can find himself.

Whitney:  Dan’s Vice articles:

How My Ex-Girlfriend's Maid Taught Me Everything I Ever Needed to Know About Love (#MaidAdvice)

The Art of Finding A Girl Who Is Smart and Gorgeous in New York City - It's Possible! (#WifeMaterial)

I Made It Out of Brooklyn, and You Can Too! (#BoroughBias)

Don't Let A Cheating Scandal Ruin Your Marriage: How Our Counselor Saved Our Marriage AND
Our Lives! - a joint piece by Serena and Dan van der Woodsen (#TherapyWorksMiracles)

Pay Your Groundskeeper Well, and Everything Else You Need to Know About Buying a Farm Upstate (#HamiltonCountyHideaway)

Kerensa: This is so so so good that I don't even know how to respond.

However, my friend just told me that Dan wouldn't even be an editor at Vice, he'd be like a junior staff writer.

What else in this episode stood out for y'all other than Serena's ANNOYING giggle?

Whitney: I'm not sure if it's because I live in Brooklyn now, or because I'm not 16 years old watching this, but it annoyed me slightly how earnestly the show tried to pretend it knew anything about Brooklyn besides the clichés. The coffee shop, if I read the door correctly, is called "Communitea" which, vomits. It's not that Brooklyn doesn't have 200 coffee spots exactly like that, but I don't feel like Dan would ever be seen there or Vanessa would enjoy working there. Plus, the room Serena uses for her gift is a Bedford Avenue art studio (conveniently obvious from the giant "Bedford Avenue" logo painted on the wall). It seems like the show is yelling on deaf ears about how hip it can be when not dealing with UES hotel locations. I don't why, but it rankled me just a little throughout.

Emma: That makes sense. TV versions of things, especially on a show like this tend to pick the most exaggerated portrayal of something and then run with it.

The one other thing I want to mention is the another maybe real life Gossip Girl coupling with Rufus and Lily (I really want that to be true). This is just the start of all the drama surrounding this couple and while I grew to dislike them as an actual couple at this point it's sweet in that 'adults who have trouble addressing their feelings' kind of way. Plus Bart is terrible so of course I want Rufus to say how he feels before it is too late (he doesn't).

I don't think Gossip Girl managed to weave the adult stories with the teens as effortlessly as something like The O.C., but I do appreciate how Eleanor and the Rufus/Lily/Alison triangle (with gross bonus Bart) add something to the messiness of relationships on this Christmas episode.

Random nitpick but isn't Victoria's Secret a little lowbrow for the Waldorf's? I know it's just product placement but it is a brand I can imagine Blair scoffing at. Agent Provocateur would be a better fit.

Kerensa: Yeah, the Rufus/Lily/Alison triangle is zzzzzzz. I loved Rufus and Lily and like y'all grew to hate them. Gossip Girl wasn't super great at blending the adult storylines like The O.C did. But I mean Alison basically completely disappears after this! But it does add a lot to the messiness of relationships in the episode, ha, especially when you think about the whole Serena and Dan pairing!

EMMA! I thought the same thing. Blair wouldn't fuck with Victoria's Secret ever, especially that garbage Pink line!

Whitney: I agree about the VS sponsorship. It's something Eleanor would do on the down low for a quick buck (basically however much it takes to fuel the jet) not brag about. And there would DEFINITELY be no chance the Christmas party gift bags Eleanor was handing out would be VS. So wrong.

Next time: I’ll be seeing whether or not Saved by the Bell holds up…

FYI: Whitney McIntosh is a writer currently living in Brooklyn. She refuses to admit how addicted she is to Taylor Swift, but will happily talk about a single piece of Alicia Florrick's wardrobe for hours.

Emma Fraser is the creator of TV Ate My Wardrobe and spends most of her time writing about TV, fashion and costuming; Olivia Pope's coats, the wigs on The Americans and April Ludgate's sweaters are just as vital as talking Team Noel or Team Ben and other '90s/'00s teen shows.

Categories: Tubin' Tags: christmasgossip girl
Kerensa Cadenas's photo About the Author: Kerensa is a writer living in Los Angeles. She grew up on binge reading Sweet Valley High and watching Saved by the Bell at a very young age. Hence, she is now unable to grow out of this life-long phase. She loves terrible teen television, young adult novels and probably listens to One Direction more than she should. She also enjoys more adult things like margaritas on patios and dance parties. A Marcus Flutie/Nate Archibald man-hybrid remains her ideal.