Is it just me or is Hillary Clinton basically the real-life version of what Paris Geller would have been had the television show Gilmore Girls lasted another 20-30 seasons? Clinton is about the right size and shape for a middle-aged Geller, and they're both brainy and driven blonds. Neither seem to be quite comfortable in their own skin and they both seem to want to succeed just a little bit too much to the point that it comes across as being a little scary. I'm also not sure either is entirely comfortable with the normal human range of emotion. Did you notice how awkward Clinton seemed during the primary campaign when she was trying to be more personable? It was a bit painful at times. As for Geller, her having been the first legitimate female candidate for president wouldn't have been a long shot at all in the Gilmore universe.
Of course, if Clinton is the real world's version of Geller, then she needs to be surrounded by people who also resemble Gilmore characters. Figuring out who Bill would have been on Gilmore Girls was pretty easy. He'd have been the slutty blond friend who was always with Paris in the Chilton seasons. It's a change of gender, but I can think that's a very minor change compared to the similar motivations between character and former president. I think Chelsea would have been the nicer black-haired girl who always seemed to forget she was supposed to hate Rory in the first season.
The part of Rory has to fall to Barack Obama, and he fits the bill better than expected. First, he and Clinton had a very tense and heated rivalry early on in their relationship only to find mutual respect and understanding in the end, at least in public. Sure, in real life Clinton is just using Obama as a stepping stone for her own ambitions while Paris genuinely admired and loved Rory, but that's all out of the public eye and can only be assumed. Obama also shares a much less intense personality with Rory, although I can't really see him being the anal list-maker that Rory was. He comes across as genuinely laid back while Rory just seems that way when compared to Paris. There are also the similarities in intelligence and being able to be driven without becoming unbalanced. However, I find it hard to believe that Rory would ever be a smoker. The main problem is that Obama is also not, nor has he ever been, a cute young girl. I didn't say this was a perfect metaphor, but I think I was able to stretch it farther than you thought I could.
I tried to take it out past this point, but it just didn't work. Our current first lady resembles in no way any of Rory's boyfriends and I can't really find a way to force Rahm Emmanuel into Lane Kim's fictional skin.
But you couldn't imagine how hard I tried.