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DONUT RANT:
Going back to Donut fans saying "Poor D deserves to be number one for someone."

See, this is why I have grown to loathe his character and frankly it annoys me that Penn wants a DB endgame.
That would mean every single lead female character on this show picked the Donut first. He was the love of Serena, Vanessa and now BLAIR'S life? Are you kidding me? What kind of storytelling is that?
Tell me someone PLEASE tell me - how has D earned that as a character?

It's not like he's faced any sort of obstacles. His life has been a fucking Mardis Gras compared to all the UES kids. He has a loving and supportive Dad. Both his parents encouraged him growing up (they gave him pens and books as a kid) and told him how great he was. The worst thing he went through was watching his parents breakup because his mom decided to go off and pursue her art at the expense of the family. That's difficult but it doesn't even compare to the shit Serena, Chuck, Blair and Nate have had to deal with with their respective families.

Donut is also the LUCKIEST character. Every girl he's wanted has fallen for him. He got his dream girl Serena at the beginning of the series. He gets his NEW dream girl Blair at the end of the series too? In between he got a movie star (Olivia), his BFF and I would argue his intellectual and artistic soulmate Vanessa, and a myriad of stalker types from Georgina (who hand picked him to be her baby daddy because she liked him so much) to Nelli Yuki who crushed on him to random chicks at NYU.
He gets published in the New Yorker before he's 18. He becomes a successful author before he's 21. He has movie deals, access to money and society through Lily and now Blair. He started the series as an outsider but rapidly became the biggest Insider of them all.
Everyone loves him or at least grows to respect him and think he's AWESOME. He ruins the girls that he leaves (notice, he always gets to do the breaking up. Never them.)

But to be fair, I shouldn't hate on Donut just because his life has been good relative to everyone else on the show. Perhaps if he was written as someone that's extraordinarily awesome, brave, loyal, kind, etc then it would justify his amazing winning streak.
The problem is, Donut has never been written like that.

As I've said numerous times, his one big virtue is that he's nice to all the UES'ers when they are down on their luck. It's how he won Serena (she was stillin shame over being Bad Serena and being with a nice non UES guy was her redemption in many ways), Nate (he was homeless when he became friends with Donut), Blair (Second half of S4 she was still struggling with her feelings/relationship with Chuck and this season she's been in crisis with the paternity issue and later losing her baby and Chuck in one fell swoop), and Chuck (early S5 his issue with being able to feel after losing Blair).

But other than that one virtue, Donut has NOT been written as an extraordinarily heroic, brave, kind, loving, loyal, etc character. If he was written like that then I could see why the writers would feel it makes sense that he be rewarded over and over again.
Instead, they've actually made him rather flawed.

Donut was very hypocritical and judgy in the early seasons. He's not a sweet natured guy. I'd characterize him more as snarky and at times very cocky and confident. He isn't the humble, modest hero type if that makes any sense. He is no Seth Cohen. (He isn't a Pacey Witter either for a number of reasons, one of which is that he never faces any obstacles and is not a true underdog).

He isn't a particularly loyal friend (e.g., how he treated Nate over Serena; how he treated Chuck (a quasi friend but Safy said they were "brothers" so..) over Blair; how he treated Blair at W magazine; the downright CRUEL way he treated Vanessa at the end of S4, etc)

He isn't a particularly loyal brother given that he's smooching the girl that bullied his sister in high school and then banished her from her own home.

He isn't a particularly loyal boyfriend. He has a pretty consistent history of emotional cheating (he falls in love with new girls easily and leaves the old one in the dust). He cheated on Vanessa with Serena.

He's a horrible ex boyfriend. The way he has treated both Vanessa and Serena is really inexcusable to me. (But I guess if one is vicariously living through Blair, hates Chuck and Serena, has a capacity to overlook or not care about D occasionally making biting comments to Blair, has the capacity to overlook or not care about his occasional domineering/macho streak, and one doesn't give two shits about any other character or relationship on the show? I can see why you might want him with Blair).

Hell he isn't even much of a White Knight when you compare him to Nate.

And this season he's been downright shady at times.

Now, NONE of these flaws are a huge deal. No, he did not sell his girlfriend out for a hotel. No, he didn't smash glass by his ex-girlfriend's head in a moment of desperation. But my point isn't that Donut is BAD and worthy of HATE. My point is that there is absolutely NOTHING and I mean NOTHING about Donut's character or journey that makes him especially WORTHY of being constantly rewarded, let alone end up with Blair.

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