NY1 traffic reporter and Complex Magazine dating columnist Jamie Shupak went to DC this weekend to see what Washington’s “Nerd Prom” is all about. While her and her boyfriend, New York Times media reporter Brian Stelter didn’t attend the actual White House Correspondents Dinner (long-standing NYT company policy) they did hit all the weekend’s festivities. It’s Friday evening and I’m standing at the bar of The New Yorker’s party at the W Hotel with New York City Police Commissioner Ray Kelly. We’re playing the first of many rounds of “New York – DC – Hollywood” which is exactly as it sounds. You point to a person in the room and based on their outfit, guess where they’re from. I warm him up with an easy one. “Dark blue satin,” I say, gesturing to a woman nearby who looks like she just walked off the floor of the Senate. He laughs to avoid answering. (The Commish is so politically correct.) He then looks down at his own getup – head-to-toe black of course – then back up to me. With a shrug and a smile he smirks, “New York.” This game, just like the intersection of DC political types, New York media, and Hollywood celebrities, is both fascinating and funny.

The White House Correspondents' Dinner, which took place Saturday night in DC, always makes for an interesting red carpet. The event is a strange mix of politicians, New York's media power players, and celebrities from the A list on down to the D list. We're talking President Obama and Kim Kardashian in the same room ("Why is she famous anyway?" Obama joked during his speech). And that makes for some very interesting fashion. Take a look. And watch President Obama's hilarious speech first. He's so good.