When Raina overhears him in the middle of a bitter argument with Lily, his adoptive mother who presents as a kind woman only out to support him, she draws a line. Raina Thorpe deserved more airtime, especially considering there was so much to unpack about her life, not the least of which being that she had to turn her dad in for the accidental murder of her mother.
Nate acts as a kind of mentor to her, since he is a few years older, and they end up kissing once in Season 2. The rest kind of fizzles into an unrequited crush, with Jenny continuing to pine for a while before moving on with very little damage.
One of the weirdest dynamics to emerge out of this almost nonexistent romance is the rivalry between Dan Humphrey and Nate. They already had some bad blood because they were in a not-so-subtle competition over Serena for several seasons, one that went into periods of passivity but never actually absolved. When it comes to blows between the two guys over Jenny Humphrey, it definitely seems like Dan is taking out other, unexpressed aggressions toward Nate.
These two really, really did not have to be such a disaster. Jonathan seemed to have endless patience for Eric as he sorted out who he was, and went through several especially moody phases. Jonathan deserved better from Eric, who continually gets caught up in the cat-and-mouse drama of the Upper East Side and ends up morphing into the type of person that the two had previously been united against. In Season 4, when Jonathan realizes that Eric is not necessarily slipping into these bad habits but maybe that they are characteristic of him as a person, he finalizes the breakup for the last time.
His disappearance highlights how little the show let him develop as a full character separate from this dysfunctional relationship, which is disappointing since these two were the only queer couple featured on Gossip Girl. Okay, it might not seem like this pairing belongs anywhere on this list; after all, they are one of the rare couples that stays together—as much as breaking up and getting back together one million times before getting married can be considered "staying together.
It can be hard to remember everything that Chuck put Blair through selling her for a hotel, lying at every turn about basically everything, devising elaborate plans to tarnish her reputation, going into hiding in Paris to avoid ever seeing her again, etc. As much as they seem to make each other happy in a strange, twisted way that only they can, their relationship is built on the backs of a lot of casualties, from those they led on while trying to make the other jealous to deeper, more substantial relationships that were never going to work out while the other still lived and breathed.
Forging a bond that was more compulsion than love, the two do come to a kind of mutual understanding, but their complicated history cannot be completely erased. Speaking of the casualties of the Blair and Chuck fiasco… Nate, while objectively one of the least likable characters on the show, definitely got the short end of the stick here.
The series begins after Nate, the long-time partner and established marital prospect of Blair, cheats on her with her best friend Serena. While Serena leaves town shortly after the incident, Nate stays behind and deals with the fallout. Which also, another thing is my cousin, she's a huge fan of Gossip Girl.
And when my parents and I called her, she was really surprised and elated that I was in it, which was pretty cool. TV: I love that. How much did you learn about the old series as you were preparing to play Milo? AR: Yeah, I learned. I looked at a lot of stuff about Georgina Sparks, who is my mother in the show, and how evil and I was thinking of a word to sound fancy, but how evil she is and how she sets up a bunch of stuff and different confrontations that could potentially hurt the others.
She's just like an agent of chaos. I feel like she's like Dr. Evil and I'm Mini-Me. TV : Did you get to talk to Michelle Trachtenberg at all about that character?
Do you think that's how it's going to be with Milo? Will he just kind of appear periodically to cause chaos? AR: Yes, that's definitely what I'm hoping for. Whenever things seem all fine and dandy and nice and all the conflict's resolved, he comes in to mess everything up again. AR: Oh, she's super nice. Her character Zoya is who Milo is interacting with the most. It was cool working with her. We talked a lot and yeah, overall, very cool.
Very fun to talk to. What you need is a coup. Would you ever strategize against someone like that? AR: I agree with him because whenever I I'm not as smart as him. I'm not as devious and strategic as him, but if I were to strategize against an enemy I had or something, I would take the time to consider something they don't expect like that. TV : Milo skips a couple of grades in the show.
He's in eighth grade, I think. Would you ever want to do that? AR: I actually did. I skipped a grade, just a single one.
I went from fourth to sixth grade, and it's something similar that we both have in common. TV : What's that like, because that's kind of a big jump? Sixth grade is a big year. AR: Yeah, I guess. This is the first year of middle school. It was weird going to another school when I'm supposed to be in another year at my school. But it's good. I still keep in touch with all of my friends from my elementary school, and I made a few new ones.
TV : That's great. I was watching another of your interviews where you were talking about remote learning and the pandemic and how it isn't that different from your set tutors.
Meanwhile, Serena is trying to prepare for the SATs but agrees to go to dinner with her anyway. During the dinner, Georgina drugs Serena and brings her back to her hotel. As a result, she tells Georgina that she no longer wants to be friends and warns her not to contact her again. Angry at this, Georgina sends Serena a USB drive that contains a video taken of the night she spent with Pete Fairman, a mutual friend who overdosed on cocaine in a hotel room with Serena and Georgina.
Soon after, Georgina invites herself to a dinner with Serena, Lily , and Eric van der Woodsen ; during which she outs Eric for being gay. The next day, Serena tells Blair, Nate, and Chuck about what happened the night of the video and the three vow to take Georgina down. Serena eventually tells Dan the whole truth, and Dan works with Blair to take Georgina down.
They bring her parents back to town; and they announce they're going to send her to a boot camp for troubled girls as punishment Much 'I Do' About Nothing. Serena begins dating a new guy, Gabriel Edwards , who Blair and Chuck suspect is lying about his motive with her. When they learn Gabriel supposedly met Serena on the night she was out with Georgina Desperately Seeking Serena , they go to see Georgina and find out if it really happened.
They track her down at a bible camp where she has supposedly reformed her ways and become good Southern Gentlemen Prefer Blondes. Georgina agrees to return with Chuck to the city and they team up with Blair, Nate, and Serena to out Gabriel and his accomplice, Poppy Lifton. Blair gives Georgina a makeover and they set her up to meet with Poppy and buy into her ponzi scheme to entrap her in front of the police.
However, the plan fails when Serena ends up getting arrested. Blair blames Georgina for sabotaging the plan; but Georgina later turns around and reverts back to her old self, and goes off to take care of Poppy herself The Wrath of Con. In The Freshmen , Georgina appears in Blair's dorm and announces that they are roommates. She later throws several parties to ensure Blair's place on the outside and begins a friends with benefits relationship with Dan. Later, she pits Blair and Chuck against each other but when Serena finds out what she did she informs Dan, who breaks things off with Georgina.
Once he does so, Georgina overhears Vanessa talking with Scott Rosson , a boy who is Lily and Rufus Humphrey 's love child, unbeknownst to everyone else. She then decides to go to Boston and befriend him The Lost Boy. Knowing that Vanessa knows who Scott really is, she blackmails her into trying to break the two up. Not wanting to be controlled by Georgina, Vanessa reveals what she knows to Dan.
At Rufus and Lily's wedding, Georgina brings Scott and tells everyone there who he is. In the season finale Last Tango, Then Paris , Georgina goes to see Dan at the loft and reveals that she is heavily pregnant with his baby.
By the premiere Belles de Jour , Georgina has given birth to her son, Milo Humphrey , and effectively moved into the loft with Dan; who hasn't told anyone about Milo. Soon after, Vanessa finds out and Georgina goes to a luncheon hosted by Lily and Eleanor Waldorf to introduce everyone to Milo.
Dan comes shortly after and is asked by Rufus if he's sure Milo is his son. He asks for a paternity test and Georgina shows paperwork from a doctor that says he is the father.
As a result, Dan signs the birth certificate. Right after he signs, she leaves him a note explaining that she is going to the spa. Meanwhile, Rufus figures out that it is biologically impossible for Milo to be Dan's son due to the blood type he is Double Identity. In the days after, Dan discovers that Georgina is not at a spa and tries to track her down. He initially considers giving Milo to an orphanage, but later decides to keep him, with the help of Vanessa. But when his wife Oksana found out Georgina was pregnant, she hired some people to kill her.
In order to save herself and Milo from being murdered, she set Dan up to look like the father. She then leaves to move back in with her parents, who she was reconciling with while gone, and takes Milo with her The Undergraduates.
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