#despite difference in vibes i feel like both serenessa and dair sort of like

[mrs-nate-humphrey]

how do u think a dair + serenessa double date would go? 👀

i tried my best, but tbh i think it’d be chaotic because i feel like the kind of things serena and vanessa would do on dates vs the kind of things dan and blair would do on dates would be wildly different! so if any of these options feel ooc that’s probably why. this was a fun ask though! and i came up with 5 potential double dates so hopefully at least ONE feels correct....

under the cut, because it got long (of course it did) 

pre-date, dan & vanessa get ready together, and blair & serena get ready together. i think blair would do fishtail braids for serena or something, and serena would give blair input on what to wear, zip her dress. they'd fix each other's make-up. dan and vanessa would be doing the same thing! vanessa fixes dan's tie (she's had practice with nate's ties after discreet make-out sessions at his WASPy relatives' place, she knows how to fix a tie) and smooths down his suit. dan probably does something elaborate or fancy or pretty with her hair, braiding ribbons in or something (he grew up with jenny, he knows how to help a girl look fancy for a special occasion).

option 1:

they'd meet at a neutral location, like a park or something, and vanessa and serena would walk around slightly ahead of dan and blair, arms looped together, talking excitedly about something that dan and blair exchange puzzled looks at. dan and blair would walk around too, more leisurely, not really saying much but just enjoying each other's company? or maybe the would talk a lot because, well, they're dan and blair. eventually, blair reaches out for dan's hand and holds it and dan turns a fascinating shade of pink

they're in the park for an hour, until they either get bored or get kicked out for hanging out in the kids area because they're making the children wait lkhfdlkfgklgf. i think vanessa and serena would spend a lot of time on the merry go round while dan and blair stare at them with disappointed horrified wonder, like "how are they going so fast and not throwing up?" / "i don't know" . dan and blair would just sit on swings and not swing LKFHLKDGH.

after this, they do dinner at a posh restaurant, blair's choice. 

option 2:

art gallery date!

dan and blair are being their lovely pretentious selves, going deep into symbolism and historical context and interpretation of paintings using different frameworks and like - vanessa knows enough to join them in the debate, but like....

serena is right there staring at various pictures and saying things like "this shade of green is so calming and soothing, makes me think of peppermint" or "if i could only see one colour for the rest of my life, it'd be this violet" or "this blue feels so melancholic" and vanessa finds herself so so so curious about what serena means, and she really wants to know what her girlfriend means, so she loops an arm around serena's waist and asks all the right questions (she's not trying to ask the right questions, she genuinely wants to know), all "what do you mean by that" or "why do you think that is" or "melancholic how? could you give me another example?"

serena is touched that vanessa actually wants to hear her interpretations as opposed to being academic or whatever

meanwhile dan and blair are two seconds away from yelling or frothing at the mouth. they are looking at a picture of sisyphus and arguing about what it means.

"do we do something about that?" serena asks. "nah, they're flirting," vanessa says.

db disappear for a hot minute, and when they return, blair's lipstick smudged on dan's face, serena and vanessa do a GREAT JOB at keeping their expressions neutral

option 3:

beach date! blair hates it because of all the sand but then dan piggybacks her everywhere and she's too busy having fun to really think about the sand. until dan runs right into the waves and she's shrieking, and she's like, humphrey do you know how much these clothes cost, and he thinks she's going to cry or something, and she knows he thinks that, because the next thing he knows, she's pushing him back into the water and he's spluttering because he actually dressed up for once (yes, he dressed up for the beach, his fancy ass girlfriend is totally rubbing off on him)

serena and vanessa just look at them like why are our friends like this

serena gets a surfboard and vanessa watches her and cheers

dan and blair are both just lying on a picnic blanket (vanessa's picnic blanket, now covered in seawater, thank you very much) and laughing so hard that vanessa goes, 'hey, are you both sober? did you show up here drunk?' and that just sets them off again

option 4:

open mic! blair bullies dan into performing a poem, and he goes, i know you write too, waldorf, so you’ve got to do something as well, and she does!! she’s never really thought of herself as a writer before but at that minute, she does. 

vanessa gives serena a poem she’s written on the back of a receipt from some coffee shop, and serena goes and performs it, and dan and blair are both like, why didn’t you perform your own poem? and vanessa’s like, i wrote it for serena to perform. it’s a poem meant for serena in every possible way 

they want to tease her for being a sap but they unfortunately have no ground to do so 

after this they go to some nice, fun, extremely casual eatery in brooklyn and blair complains loudly and at every possible opportunity but once they’re actually there, she’s all smiles. she steals the salad off dan’s plate

serena talks to vanessa later, about ‘did you give me a poem to ensure i wouldn’t feel left out?’ and vanessa goes ‘no i gave you a poem because i wanted to. because i can’t stop writing poems about you and you mean so much to me’ 

option 5: 

vanessa takes all of them to a lesbian concert

blair’s initially awkward about it like ‘i don’t want people to think im a lesbian!’ and dan is like “you can just kiss me in that case” and vanessa is like, “funny, nate never complained about that”

later, blair talks to dan about how the real reason she’s iffy about this concert is her hugeass crush on serena from when they were kids, and she’s over it, but sometimes she remembers it and it always hurts

and dan, to her surprise, gives her a hug and tells her about the hugeass crush he had on vanessa, and how she took him to these concerts all the time before she left and he kept wondering what it meant, because it always felt like a date, their bodies always smushed close together because of the way the crowd would be, and he tells her that it hurt, but he wants to go to a concert with blair, to make new memories or whatev

blair is like ‘nothing about this experience sounds appealing’

dan is like, ‘give it a try before you judge it’ 

and blair does and she hates the crowd as expected so she and dan sit outside together and she feels mildly awful about making him miss the concert, but they’re near one of the doors and they can still hear the music and blair thinks the band isn’t half bad and she tells him that, and dan laughs, like, ‘see? i knew you’d like them’ and blair gives him an incredulous look and kisses him 

and keeps kissing him

serena and vanessa come out of the venue laughing, faces pink and flushed, and they look at dan and blair, who are standing there and smiling and looking sort of quiet and at peace and happy despite leaving in the middle

vanessa checks on blair, and blair smiles at her and says it’s all good, and v believes her, because she looks really happy