Time for a throwback…all the way back to the beginning of the Gossip Girl series with a prequel.
If you’re wondering why I waited this long to read this, it’s because I’m just reading them in the order they were released/Wikipedia had them. But you could definitely read this as the very first book in the series and it would fit in.
In this book we get the origin stories of how our lovely Upper East Siders came to be. Why Vanessa shaves her head, how Dan became a poet, how Nate became a stoner, how the big Nate, Serena and Blair love triangle came about and even about Jenny developing her massive chest. It’s all wild and it’s all right here.
Sadly the only origin story we don’t get is Gossip Girl herself. As far as I know she doesn’t reveal her identity in the books which I think is probably for the best. The TV show did a terrible reveal and I didn’t like it. I mean seriously. DAN HUMPHREY? As if. Especially in the books he could never be Gossip Girl lol.
Anyway that’s a rant for a whole other day. Let’s dive into this book shall we?
Starting off with Blair, our B. Gotta love her. So this is before she is with Nate and obviously all she is thinking about is being with him. She’s had a crush on him forever and feels like she’s gonna explode if he doesn’t marry her.
To save some time and explaining her scheming I’ll just let you know her and Nate do get together. But all Nate wants is to have sex and he thinks he is gonna get it from Blair because she loves him and he loves her so like it’s a no brainer.
As if. B begins to string Nate along and telling him she’s not ready but they can do it in summer, or after summer, or christmas…and you get where I’m going. Poor guy. Just wants to get laid lol. But I enjoy Blair being sneaky and manipulative. It’s the Blair we all know and love.
On top of that we discover the ruby ring she is so fond of was a gift from Nate. This is also when I realise that the ring hadn’t been mentioned much in the last few books and when it was it seemed out of place. Again, the effects of a ghostwriter. (I know I always sound negative about the ghostwriter but like there are just certain things you notice when suddenly a different person is writing the books).
We also discover she doesn’t handle the news about her father leaving her family for a gay man and so this is where her bulimia comes from. The book handles it in a kind of cast offish way which it has always done. Like oh Blair just went to throw up, she felt like she was gonna vomit hearing news she didn’t like. That kind of thing, definitely wouldn’t fly with that kind of writing now but I guess in 2007 it was chill.
Thankfully somewhere along the line Blair just stops throwing up. I don’t remember when but I feel like it hasn’t been mentioned in the books for ages so I guess she magically recovers. Kind of like how on TV they showed it like one time and forgot about it.
Time to move along to Serena. Our golden girl. Who is also madly in love with Nate. I guess they planted this love triangle early. And that’s fine. It was written a less annoying this time and plus this was the beginning, way before everything else so it’s fine.
Turns our Blair was not the first to kiss Nate. It was S. They kiss in bed while Blair is sleeping right next to them. So romantic lol. But this is when Serena knows for sure she loves him and Nate loves her back.
Serena was planning to tell Blair this but when she saw how Blair’s family was falling apart she thought the least she could do was let her have Nate. Even though it killed S to see her two best friends get together.
It was interesting to see Serena’s martyr act thinking she was the lost selfless person ever. But it got old real fast, like we get that you are heartbroken but time to move onto bigger and better things.
I can understand why she was pissed at Nate for just choosing Blair after they kissed and everything, but can she really fault Blair if she didn’t know S loved Nate too?
Anyway yeah I was kind of over Serena in this one. Just pining after Nate while also being a shitty friend to him and Blair. Not cute.
That being said, we did find out about how Nate “parted S’s red sea”. I mean we already knew because they’ve talked about it in previous books but in case you needed to relive it, it’s right there.
After all that goes down Serena realises she shouldn’t have slept with Nate because he is with Blair. But at the same time she is not going to stick around and watch them be in love anymore so that’s why she decides to go to boarding school. Which is kind of lame but then again it’s selfless Serena, leaving to let her two friends be happy.
Then we have Nate. And while the girls have been passing him back and forth like a game, it’s not like he hasn’t been responsible. In fact when you get right down to it, Nate is just a dick lol.
First he kisses Serena, then Blair kisses him and he decides to be with her, but once she doesn’t wanna have sex with him he decides to call up Serena and they have sex, then Blair comes back into town and he’s like “right my girlfriend”. I mean he’s trash hahaha. Sure Nate in the TV show is kind of trashy too but he is also cute in that he doesn’t mean to hurt people’s feelings and he isn’t a stoner on TV.
But yeah I guess the gist is with Nate is that he’s horny and helpless when it comes to pretty girls. He wasn’t even gonna get with Blair or Serena to begin with his was after some other girl that introduced him to weed. He liked how he felt and then just jumped in head first to become a fulltime stoner.
Safe to say him and the first girl didn’t work out. And he thought Serena wasn’t interested in him anymore when he saw her go kiss Chuck at a party. Even though she only went over there for Blair’s benefit. Not that Nate would know that. Which is how he needed up with Blair.
Nate can be kind of cute when he wants to be because when he gets with Blair he works hard to distract her from her crappy family and buys her pretty things from Tiffany we love that. But at the same time he isn’t getting any for her so the only logical thing would be to call Serena.
To be fair he only wanted to see her at first because he hadn’t seen his friend for forever but then they had sex and well…we all know the rest.
I will still stand by Nate being trash for jumping between the too. I guess the best thing he ever did was leave them both and sail around the world…
Moving on down to Brooklyn and the Upper West Side.
Dan and Jenny. Turns out both the Humphreys have an unhealthy obsession with S. Who can blame them when she is so perfect.
I think I was shocked by Jenny more just because I didn’t know her obsession ran so deep. Literally her stealing Serena’s bra and drawing all those pictures of her and everything. Crazy.
Plus in this book Jenny was twelve haha and obsessed with wanting to grow her boobs. She didn’t know she would end up with the chest she would. But at the time she was desperate to make them grow and so she ordered breast enhancement supplements lol.
It’s also kind of weird how she insisted on showing Dan the progress of her boob growth. Like I guess they are super close because they don’t have a mum but there are just some things you shouldn’t share with your brother. You should also never ask him to measure your boobs but that is a thing that happens too. Wild.
Over time Jenny’s boobs do grow. She stopped taking the supplements after like a week because Vanessa told her that she would grow naturally anyway. It’s just kind of funny she wanted them anyway. Plus she goes from loving her boobs to hating them real quick. So I guess you can never win.
So yeah…that was Jenny. Then we have Vanessa who joined Constance and had a full head of hair. I can’t believe it either. She decides that she needs to do something shocking to stand out from the girls at her school and what better way to do that than to shave your head. Not to mention Blair was with her at the time, cute.
Vanessa and Dan become friends after both getting locked out on the roof at a party and Vanessa instantly takes a liking to Dan. She knew he was different like her so maybe they could be friends, or more than that. It turns out Vanessa really loved Dan at the first sight of him and even tried to kiss him at one point.
It is kind of cute to see Vanessa wanting to be with Dan this way. In the other books she seems kind of edgy but in this one she is niave and just wants Dan to like her back. Well, until she finds out he’s like everyone else, in love with Serena. Then she’s mad. Who wouldn’t be?
I get that she was upset with Dan but at the same time she was definitely trying too hard haha I’m glad they friends though. The book talks about her being really into photography but not film making so I guess that comes after…I guess it’s not a huge leap from photography to film making. But I’m surprised it’s not mentioned.
Anyway moving on to, last but not least, Dan. Turns out he wasn’t always a smoking, depressed poet. But he always drank his coffee by the bucket load. So Dan is over here obsessing about Serena, wondering if she will ever remember him from that one party they were both at. Rufus, his dad is over Dan’s moping and suggests that he try poetry to express his feelings.
This lightbulb moment happens and suddenly Dan thinks, yes, that’s it. He writes some words down and decides he is a poet. His muse is Serena and he will write her all these love poems and she will read them and when she finds out it is him she will fall in love with him and they’ll live happily ever after. As if.
His poems are obviously super terrible, but he decides to give one to Jenny to slip into Serena’s locker anyway. She reads it and thinks it’s dark and kind of cool someone would write poetry for her but she is not fussed on finding out who wrote it. Let’s be real the girl probably gets millions of letters and poems from admirers, Dan will have to step up his game.
Dan also decides after he meets Vanessa to randomly start smoking. I guess he thought it went with his dark poet vibe. And so, this Dan we all know and kind of like was born.
Honestly not surprised that he just fell into poetry and smoking. That kind of sums up his life, maybe he is not so different from Nate. I mean he fell into poetry and it stuck, he went along with being with Vanessa and that was cool, he also just went with the flow when he was doing yoga with that one girl for some time…he even fell into being gay and out again haha. Dan doesn’t make decisions for himself, people make them for him, it’s only right his dad recommend he become a poet and he did. Plus Nate is the same, he just smokes weed and goes with the flow.
But yeah, after Vanessa finds out about Dan obsessing with Serena she is not too thrilled so they don’t talk for a while. It is actually Jenny who has to tell Dan that he should apologise to Vanessa because he could use a friend and social interaction. I guess it’s cute Jenny is looking out for him. So he goes to apologise to Vanessa and it looks like those two patch things up.
And that brings us to the end of the Gossip Girl prequel! This was cute. I feel like I would have appreciated it more if I wasn’t so jaded after the last few books. Anyway, one more book and we can be done with this series! Yes I know there is the spin off and also the It Girl book series about Jenny but I definitely need to read something new after being wrapped up in this world for a few months.
I think I’ll be glad to finish this series, it’s been a fun run but towards the end it just kind of got meh. Let’s hope the last book will allow us to finish on a high note.
You know you love me,
~ Courtney x