1.) Serena- Marilyn Monroe

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This pick was extremely obvious because everytime I see Serena, I think blonde, head-turner, and extremely beautiful. Marilyn was ALL that. Serena and Marilyn were sexy and seductive- making any man fall in love with them. They both have this quality where they can bring attention to people and make their heads turn when they walk into a room.

2.) Blair- Audrey Hepburn

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Blair Waldorf is the modern Audrey Hepburn. They may have some differences but they are very similar. Even though Blair isn’t as kind as Audrey, they both have fab, vintage style, making them known icons. They always have cute hairstyles and accessories. They also have classic etiquette and behavior. For goodness sake, Blair reacted a scene from one of Audrey’s movies!

3. ) Chuck- Rhett Butler (Gone With The Wind)

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Rhett Butler, known as Clark Gable, must have reincarnated in Chuck Bass. They are exactly the same! They both are filthy rich, womanizers, dark and handsome, say the best comedy lines and want ferocious women- Scarlett and Blair. This was pretty basic.

4.) Nate- Paul Varjak (Breakfast At Tiffany’s)

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I chose Nate to represent Holly’s love interest, Paul Varjak from Breakfast At Tiffany’s because I could see similarities in them. They both have that guy from next door look and they both had affairs with older women. They both also look hot in wet trench coats.

5.) Jenny- Lizzie Maguire

l_9e6a6b20a29d419b864cc6f497dc0bda2hilaryd-dot-org_lizziemcguire-premiere-26april03-hollywood0011Jenny and Lizzie make a pretty good match. They’re both wannabes- doing anything to be popular like their rivals- Kate and Blair. They’re blonde, cute and extremely annoying- not so much Lizzie.

6.) Vanessa- Andie Walsh (Pretty In Pink)

l_e0c1e04c1199bbb15131efa61b713bb7pretty_pink_300x400This is also a good match because they both are the outsiders of the scene. Having great, unique style, they share a I-don’t-care-what-you-think-of-me attitude which defines their personality.

7.) Dan- Brian Johnson (The Breakfast Club)

l_e024990d4b02740d218d23ac1048a834tumb-anthony-michael-hall-als-brian-ralph-johnsonDan Humphrey and the “Geek” from the Breakfast Club make a funny duo. They are the nerds of the scene and the sweet, reserved boys too. They are silly and cute in a nerdy way.

8.) Georgina- Kathryn Merteuil

l_4f471c841b84a57e3bf618d82a394efereg15746The flawless couple- the two meanest bitches of the Upper East Side. Both beautiful, they are manipulative, rude and fake. They want to destroy people. But hey, we all love them both.


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