Gossip Girl (2007) Rewatch- S 5 Pt 2

Happy #GGThursday!! Ready to rewatch with us? Grab a snack and settle in!

But first,

1. All photos are courtesy of Home of the Nutty unless otherwise specified.

2. Spoilers abound. Read at your own risk.

Episode 7- The Big Sleep No More

“You’re a Rhodes. If you had a boyfriend, the whole Upper East Side would know about it.”


Random thoughts

  • Is the life that Charlie has gained on the Upper East Side worth having to do Diana’s bidding and constantly look over her shoulder?
  • Why did Dan stay at home, of all places? If he wanted to keep up appearances and pretend that he was on his book tour, he probably shouldn’t have stayed at his dad’s loft.


There are a lot of parallels between Diana and Juliet: they both catch the eye of Nate and get involved in a romantic relationship with him, attempt to get close to Serena to keep her unaware of their hidden motives, all for some mysterious agenda that will be revealed later in the season. The only difference here is that one was trying to avenge their wronged brother while the other is only interested in climbing the corporate ladder.

Speaking of, why are Nate and Serena so trusting in the first place? Have they learned nothing in the past four years? Think, Serena: why would Diana have such an interest in setting you up with some random guy off the street? What’s in it for her? Serena is an adult; she doesn’t need a matchmaker to get a date with Max — he was already interested in her. S and N’s constant obliviousness is growing stale.

Episode 8- All The Pretty Sources

“Girls, I have been trying very hard lately to be good. Yet I don’t feel the slightest pang of guilt unleashing my attack dog right now. And I should warn you, he’s trained to go after fake Prada.”


Random thoughts

  • You’ve gotta give Ivy credit; she’s one heck of an actress.


I can’t wait until Louis is out of the picture for good. First, he pulls a Chuck on Blair to keep him away from her, then he begins to question her friends’ motives? Far be it from me to disagree, especially given some of the things that they’ve done to each other in the past, but he’s only been back in New York for two seconds and already stirring up trouble. Also, why is he subscribed to Gossip Girl blasts anyway?

Something I never liked about this show was how demeaning Chuck would be to Dan. However, they’ve seemed to become pretty cordial over the years. Unfortunately, Dan has to provide exposition on his life ad nauseam to the point that I could go for a good Bass style insult, but we don’t get the privilege of that in this episode.

Episode 9- Rhodes to Perdition

“Nice try, the bait and switch, but I was a teenage bulimic and my father came out when I was 15. This isn’t my first analysis.”


Random thoughts

  • I find it odd that Max has yet to be in the same room with both Ivy and Serena.
  • Ivy knows that the best way to win an argument is to build up your allies. There’s strength in numbers. Poor Max didn’t stand a chance.


I’m glad Nate has been able to land an awesome job as Editor-in-Chief…. but at the hand of his grandfather? I guess nepotism wins out yet again. However, I have to give him credit for seeking out the truth, even if it’s at the risk of tarnishing his family’s reputation.

I think Max is supposed to represent the typical outsider who gets greedy where dollar signs are involved. He was a genuinely nice guy who caught his girlfriend in a lie and has suddenly come into the possibility of more money than he’s probably ever possessed in his life. Now he’s blackmailing Ivy and using Serena in the process? They weren’t lying when they said the love of money is the root of all evil.

Episode 10- Riding in Town Cars with Boys

“Try as you might, you don’t scare me. I’m sorry to inform you that my love for you is unconditional.”


Random thoughts

  • Shout out to the ceramic cat callback from season 1.
  • How icky is it to be talking to your stepfather about your romantic relationship with his son?


When it comes to Blair and Chuck, it is very important for her to make whatever decision she feels is best for her future. As nice as it would’ve been for him to give her the answer when she called, she had to come to the conclusion herself or else she’d resent Chuck for forcing her hand. Besides, it’s not like he said that he wouldn’t love another man’s child. By the time Dan put them together, it was clear that Blair had already made her decision. All Chuck had to do was make his.

Episode 11- The End of the Affair?

“What is a lifetime of blackmailing authority figures and casting out townies if it doesn’t add up to the ability to at least feign a marginal level of happiness at an office party?”


Random thoughts

  • It’s amazing how empty this episode feels without Gossip Girl’s commentary. We the audience are feeling her absence just as much as the cast is, and I love that.
  • I don’t understand why Dan and Blair are walking around in broad daylight. Just because GG is silent doesn’t mean other people aren’t looking from them.


Why is Louis’s first thought that she’s having an affair? She just went through two very traumatic experiences. I’m sure an affair is the last thing on her mind. Which leads me to a major gripe I have with how Chuck and Louis behave in this episode: instead of being so focused on who she’s sleeping with or what secrets she’s hiding, why aren’t either of them seeing after her wellbeing? She’s gone through a lot. Has it ever occurred to them that she needs support instead of scheming?

Episode 12- Father and the Bride

“You’ve pitted us against each other our entire lives. Everything is a competition, and the prize is your approval. It’s the great Vanderbilt tradition.”


Random thoughts

  • How does Beatrice know all of this information about Blair?
  • Okay, I don’t like the circumstances that put Blair into such a drunken stupor, but I love seeing her be so fun.
  • Television’s portrayal of partying is hysterical. There is no way Blair would still be able to stand after 10+ shots.
  • Trip is a riot. He joins forces with Max to get back at Nate and thought he might just hit a parked car? Did he learn nothing from the accident he and Serena were in a few years ago?


It’s pretty messed up that Nate’s grandfather has such a lack of faith in him making it on his own, but it actually makes a lot of sense when you think about it. People like William, who are the patriarchs of really old money (think Rockefeller and Biltmore) want to do all that they can to keep their family’s wealth and power in tact. Part of how they do this is by pulling the strings and calling all the shots for the younger generation to simply step into with little to effort. If one of them goes rogue, it puts the legacy of the bloodline (and, by extension, the cash flow) at risk. Either William really didn’t think Nate had the guts to be successful without being attached to the Vanderbilt name, or he felt threatened by his grandson’s unwillingness to blindly follow the pack.

What are your favorite moments in season 5 so far? Let us know in the comments!


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