Gossip Girl (2007): An Encore

When I really like a show, I rewatch it. A lot. Gossip Girl is one of those shows.

I was so excited when it was on Netflix a while back and watched it as much as I could before they took it off of the streaming service.

Now, the entire series is available on The Roku Channel for free. Cue confetti 🎉

To commemorate this moment, I decided it’s time for another rewatch, this time with play-by-play analysis from yours truly.

This is the first of many rewatches that we’ll do here, and I’m excited to get started. Each week, we’ll look at a handful of episodes and add brief commentary and random thoughts that come up while watching. Comments are highly encouraged!

A quick shout-out in advance to TV Tropes – one of my favorite sites on the planet – and the Gossip Girl Wiki for helping me fact-check details both in- and out-of-universe. All photos in this post are from the GG Wiki unless otherwise stated.

Lastly, since we’ll be going through every single episode, it goes without saying that spoilers will abound. Read at your own risk.

Without further ado, let’s jump into season one!

Episode 1- Pilot

“What we’re entitled to is a trust fund. Maybe a house in the Hamptons, a prescription drug problem. But happiness does not seem to be on the menu.

Chuck Bass

Random thoughts while watching

  • Ah, the good ole days, when the cell phones had personality. I still want a Sidekick.
  • Dan’s wild haircut – it gets me every time.
  • Speaking of Dan, watching him lurk around everywhere will never not make me (and every other You fan) think of Joe Goldberg.
  • I totally forgot about the first person they had playing Blair’s mom (Florencia Lozano.) Margaret Colin’s portrayal is much better.


I kind’ve wish I was watching this for the first time, because knowing what happens at the end of the show makes it so easy to see the main characters’ defining traits emerge here in the pilot.

For example, in the scene where Serena and Blair have a one-on-one at the bar, a first-time viewer may think Serena is the loving long-lost friend who went through a hard time and is just trying to reconcile with her bestie while Blair is being bratty and insensitive (which is partially true.) However, on rewatch, it’s evident that Serena feels guilty for what she did with Nate and is trying to clear her conscience, and Blair uses her hard exterior as a defense mechanism to protect her from future hurt.

In other news, they really get the non-verbal communication down in this show. When Serena and Blair see each other for the first time after B finds out about Nate’s infidelity with S, their looks tell the story of a thousand words.

Final random thought: I’m sure this goes without saying, but the whole public drinking while underage thing is wild. Does this really happen in the socialite world? No, really. I wouldn’t know.

Episode 2- The Wild Brunch

“If you’ll excuse me, I’m gonna go back inside, not tell anyone a thing, and mind my own business.”

-Dan Humphrey

Random thoughts

  • I absolutely LOVE the opening shot where the Bass brunch is being prepped. It makes my mouth water.
  • Dorota’s first appearance. Ugh I love her.
  • We get the lovely word “fustercluck” here.


I love that Serena thought Blair wouldn’t find out about her dirty little secret. Serena spends the entire episode pissed at Nate for telling her about their rendezvous, even making a jab at Blair for attempting to get intimate with Nate in Chuck’s suite.

Serena was 100% wrong in this situation. Not only did she sleep with her best friend’s boyfriend, she didn’t even have the decency to tell her. You can understand why Blair is so upset, yet the writers seem to want us to be on Serena’s side.

Blair is the queen of making others want what she has. Look how she lures Jenny into her trap as she’s getting dressed for brunch. Jenny is hanging onto every word she says. She wants to be in so bad, and honestly, so does Dan. How he finagled himself into the lives of the Upper East Side (outside of school) is impressive.

I love the climaxes of the GG episodes, when all of the characters’ dirt comes to the surface and they rush to air out each other’s dirty laundry in a wild game of Who’s Story Is Juicier? Something to note in this one is how clearly amused Blair and Chuck are when Dan gets physical with Chuck in front of everyone, as if to say “Typical outsider. That’s not how we handle disagreements in public.” But if there was ever a reason to make a scene, avenging a sibling has to be in the top 3.

In the last scene of the episode, Serena throws her phone in the trash. You’ve got to be pretty rich to mindlessly toss $249 down the drain.

Will all of these analyses end with socioeconomic observations? Maybe.

Episode 3- Poison Ivy

“All I wanna do is just finish high school in peace and go away to a state with lots of people who don’t know who I am and just start over.”

-Serena van der Woodsen

Random thoughts

  • The choir’s a cappella rendition of Fergie’s Glamorous always gets a chuckle out of me, especially that last breathy note. #flossyyyyyyyy
  • First appearance of Chuck’s fabulously arrogant catchphrase, “I’m…Chuck Bass.”


Nate is such a pushover. GG fans know this. But ugh, it’s so painstakingly obvious in these early episodes! Between his dad and Chuck, it’s a wonder this guy has any original thoughts. Kudos to him for standing up to his dad about not wanting to go to Dartmouth, though.

Why is Serena so unbearable here? Blair is the one who should be hurt, yet Serena acts as if Blair has done something equally reprehensible. Ay, yi, yi.

This blog series may be starting to sound like a never-ending Serena rant, and I promise you it won’t be. But really. She acts like she should just be able to say sorry and things will magically go back to normal. That’s not how it works in the real world, sweetie.

Speaking of unbearable van der Woodsens, Lily truly annoys me here. When Serena’s brother, Eric, expresses interest in leaving the treatment center, Lily becomes visibly upset, causing him to reconsider just to appease her. What’s the point of showing your support when you don’t actively support the decision being made?

I should note here how much I love Eric and how he must be protected at all costs. He is easily the mature one in the family and one of the few characters on the show everyone actively tried not to exploit. I mean, look at how bad Blair feels when Eric confronts her. It’s pretty cathartic, if you ask me (I told you this blog series wouldn’t be totally anti-Serena.)

I also love watching Eric and Jenny become friends here. It was one of the rare moments in the show where a connection was made organically with pure intent and not hidden behind some guise or ulterior motive. If only their friendship stayed that way…

Episode 4- Bad News Blair

“Once you turn away from money, you see it doesn’t buy you freedom, it pays for your prison.”

-Carter Baizen

Random thoughts

  • First appearance of Carter Baizen. Why did I think he didn’t show up in the show until much later?


We see the core reason why Blair and Serena are frenemies in this episode. Serena is naturally charming and charismatic while Blair is more buttoned-up and rigid, which makes her feel like she’s always playing second fiddle when it comes to her blonde bombshell of a friend.

The whole plot where Serena helps Blair come out of her shell while doing test shots for her mom’s clothing line is a genuine attempt at giving Blair the spotlight. But, of course, she ends up being chosen over Blair as the model of choice and they’re back at each other’s throats soon after.

Luckily, this episode is one of the rare moments when Serena does right by Blair, seeming to genuinely have no clue that Blair wasn’t invited back for the shoot, quitting when she finds out the truth, and even helping Blair get revenge on her mom by stealing her clothes and running around town in them for a rogue photo shoot of their own. It’s beautiful to see, really.

Speaking of things that are beautiful to see, Dan and Blair’s heart-to-heart is touching. Too bad revealing your inner thoughts is a cardinal sin on the UES. As we’ll see throughout the series, anything you say can and will be used against you.

Lastly, here Nate goes again, hitching a ride on yet another person’s coattails and getting played in a high stakes poker game in return. Did he really think Carter gave up the high life for one devoted to humanitarianism? However, it’s this wild series of events that leads Nate to begin discovering there’s trouble at home, so maybe it was worth it?

Episode 5- Dare Devil

“I am not a stop along the way. I am a destination.”

-Blair Waldorf

Random thoughts

  • Can we appreciate for a second Blair and Jenny’s amazing plan to break Eric out of rehab? Blair’s act to distract the front desk? Hilarious.
  • I literally laughed out loud when Eric pops up at the club in the middle of the Blair/Jenny/Amanda hoopla.


In the opening scene, Rufus confides in Dan about attempting to visit his estranged wife. I hate it when the eldest child gets roped into their parents’ drama.

Here we are again with a brilliant non-verbal exchange, this time in the form of attire. When Dan comes to pick up Serena for their first date, they both clearly have different ideas of what the other has in store for them. What makes this even funnier is that Serena thought riding a Vespa in a dress would be appropriate.

Jenny gets a round of applause in this episode. Getting invited to Blair’s annual sleepover (ahem, soiree), is definitely more than what she bargained for at first. But she kills it by the end of the night, turning Blair’s prank around on her and officially landing a spot on the Queen’s cabinet.

Episode 6- The Handmaiden’s Tale

“Serena must have the hottest date ever! If he’s got plans, he’ll change them, if he’s got a girlfriend, he’ll dump her, and if he’s out of town, he’ll charter a G5 and fly home. Make it happen.”


Random thoughts

  • I hate this episode title. It reminds me of a show that truly gives me the creeps. You know the one.
  • Y’all couldn’t hear Vanessa’s voice in the house when Dan was on the phone with her? Please.
  • Jessica Szohr (Vanessa) gives me strong Mila Kunis vibes here for some reason.
  • Eleanor’s dress at her Moroccan party is to die for. No notes.
  • Ah, the old “we’re at a masked ball so all of a sudden I don’t recognize you” trope. Yawn. On a brighter note, I love Nate’s Phantom of the Opera-inspired mask.


Kudos to Blair for genuinely wanting to make amends with Serena regarding the whole Nate debacle. I’m sure a lot of it was because she’s with Dan now, so she posed less of a threat.

How Dan “just so happens” to get into these events is really interesting. He just randomly comes across a drunk partygoer who’s so out of it that he doesn’t realize he’s stealing his mask and identity to get into the party? I definitely wasn’t this clever in high school.

I was about to go in on Serena for being such a brat to Dan, but I’d be a little upset too if I was on the phone with the guy I liked and heard another girl’s voice in the background, who he then lied about.

It’s wild how alike Jenny and Serena look from behind. I even got confused for a second in a previous episode.

Nate kills me with that dumb look he gets when he’s confused. After Blair ditched him for “not trying” to start over, he stands there like a lost puppy. Probably trying to figure out who he professed his love to at the ball, since it certainly wasn’t Serena.

That’s a wrap on season one, part one!

We’re still finding our groove between what’s a random thought versus commentary, but I foresee that getting better as we go along.

Also, I know I missed some key points, especially regarding the adults in the show (namely Lily, Rufus, and Bart.) But we have six seasons and lots of story arcs to get through, so don’t you worry.

Now, here’s the fun part. What are your thoughts on the first six episodes? What did I miss? Any points I made that you disagree with (respectfully, of course 🙂?)

Eps 7-12 are coming your way next week. Drop your email down in the box below so you don’t miss future posts.

Until then, you already know how I’m ending these.


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