I've been a Milo fan since his days as brooding bad boy, Jess, on Gilmore Girls. I thought he was a much better choice for Rory than Dean (gag!). He was great at playing Jess - rebellious but secretly intellectual. He was so good at his role that The WB offered him a contract even after his character was written off the show.
PS. I'm not digging this new look. I like his hair longer!