Gossip Girl Rewatch (2007)- S2 Pt 2

Hello all, and welcome back to another week of GG commentary!

A quick note before we get into it: the screen grab tank on the Gossip Girl Wiki seems to have run dry, so all of the pictures you see here are courtesy of Home of the Nutty (thanks again, u/chairwriter on Reddit for directing me there)!

Additionally, I thought I’d do something fun this week: each picture I selected features outfits I love (of which there are a lot of throughout this series)!

As always, as there are spoilers throughout. Read at your own risk. Enjoy!

Episode 6- New Haven Can Wait

“I’m so ready to be surrounded by people more like me and less like…her.”


Random thoughts

  • Blair’s imagine spots based on classic movies & literature always make me chuckle. Shout out to My Fair Lady.
  • Why wouldn’t Dan be upset that Nate pretended to be him? Sure, we all know that Dan can be pretty judgmental, but I think this one was well warranted.
  • You mean to tell me these Yale kids all knew of Nate but had never seen what he looked like?


You can tell Lily is fighting an internal struggle to tap into her inner youth. It’s why she gravitates toward the “edgier” dress Eleanor sends over, and it’s why she keeps gravitating toward Rufus. There’s a lot of Serena in Lily, as we’ll see in just a few episodes (if memory serves.)

You can’t tell me Jenny didn’t plan Lily’s encounter with Rufus. It felt too staged for her to be wearing Jenny’s design and have such nice things about her. Regardless, it was a sweet gesture. Rufus’s soft spot has always been Lily.

Yale only wanted Serena because she was a socialite? I get that admissions offices like to diversify their student body, but I wish there had been other accolades they’d highlighted about her aside from what was probably mentioned in Page Six.

Episode 7- Chuck in Real Life

“There’s no shame if the prize isn’t worth it. You can do your own dirty work. There’s not enough in it for me.”


Random thoughts

  • This looks like the first episode where Jenny starts ditching her Little J persona and embracing her rock glam era.
  • Say what you want about Chuck, but he’s got pretty strong business acumen and an eye for watering holes. But make no mistake, Vanessa: that is no reason for you to trust him.


You can hand wave Eric’s happy-go-lucky personality by him being young and naive, but I find his optimism charming. Serena was definitely being unfair regarding Lily and Bart’s united front.

Speaking of, I feel for Lily here. Serena is being quite the brat, and regardless of how her mom acted with her previous husbands, she could stand to have some structure in her life. She’s a high school senior who gets to traipse around New York with no supervision. It’s a wonder she’s alive.

I don’t like Serena’s temper tantrum, but I get where she’s coming from. She’s a hurt teenager who’s had numerous men come in and out of her life attempting to fill the place of her father. How else would you expect her to act?

Episode 8- Pret-a-Poor-J

Random thoughts

  • Blair and Chuck are relentlessly drawn to each other because they’re too much alike.
  • I can be quite the over explainer myself, but I hope I don’t sound as annoying as Dan does when he gets on a roll.
  • Blair must’ve been pretty desperate to divulge her love life to Dan. Love really does make you do crazy things.
  • I want to make this very clear: I am not a Nate + Jenny shipper.


Do none of these characters know how to turn a phone on silent? I know that had to be a thing even with those older phones. Blair could have gotten exactly what she wanted if her phone hadn’t been ringing off the hook.

Agnes is a piece of work. Sure, she makes good points about Eleanor working Jenny to death only to rip off her designs as her own, but she planted toxic seeds into her mind to sabotage her job at the atelier. And where did that get her? Keep watching and find out.

What Dan and Vanessa don’t seem to realize is that when the NJBC (sans Nate) are hurt, they stop at nothing to get back at the culprit. Then, once they’ve had time to lick their wounds, they become human again, thinking that all is forgiven.

Conversely, people like Serena and Blair don’t understand that they can’t just go around throwing temper tantrums and expect for people to have amnesia when they’re ready to be vulnerable. It’s a vicious cycle.

Episode 9- There Might Be Blood

“…Success, people praising you… it goes away. And when that day comes, if you don’t like who you are, you’re done.”


Random thoughts


Exactly how old is Emma? We know Chuck is no stranger to robbing cradles (or at least attempting to, anyway.) Thankfully it didn’t go that far.

I really don’t like how quickly Agnes influenced Jenny. Her haphazard decision-making was what made Jenny lose her job and make some really stupid choices.

It’s sad that the only reason Blair wanted to stop Emma from losing her virginity at first was to get into Yale. As soon as she caught her mom having an affair at the bar, she could care less about poor little Emma. And she says Chuck is despicable. I guess she makes up for it by the end of the episode, though.

Two things: 1) why have Aaron leave that unnecessarily long voicemail message when he could’ve just called Serena directly and said the same thing? 2) How is it that someone is able to answer the phone midway through Serena’s voicemail?

Episode 10- Bonfire of the Vanity

“I wanted a Harry Winston choker for my birthday. Instead, I got a conscience.”


Random thoughts


Someone should have told Jenny not to put all of her eggs in one basket. Because she blindly followed Agnes and her “passionate” antics, she ended up right back at square one.

Chuck gave Bart such a thoughtful gift…only for him to throw it in his face. When you tell someone they’re no good long enough, eventually they’ll start to believe it.

I know Dan needed that recommendation, but my goodness did he make a huge mistake in getting in between Chuck and his dad. Like most characters on this show though, he makes up for it later.

So Aaron is supposed to be this cool, artsy guy who’s a free spirit and likes to come and go as he pleases. And to top it all off, he is also oblivious to how his lifestyle could upset someone like Serena. What a schmuck (I feel like his dad would say something like that).

Aaron and Agnes are easily my least favorite characters, but you know who’s my favorite? Cyrus Rose. He is such a sweetheart, and like Eric, one of the few characters in this show that must be protected at all costs. It’s hard for someone like Blair to warm up to someone, and I love that Cyrus won her over simply by being himself.

Are you rewatching with us? What are your thoughts on season 2 so far? Let us know in the comments!


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