Kaylie Hooper

If you didn't think I was going to include another trust fund baby recurring character from a Tina Fey show, again, you are mistaken because "I'm enjoying my lack of adult supervision by eating Fruit Roll-Ups for dinner. While I'm at a strip club" is an all-time line.
You were born into a dynasty of trust fund babies and can pretty much do whatever the fuck you want in life. As long as you don't go all Menendez brothers on us, look to the Jenner brothers or any girl that lives alone in the West Village at the age of 27 and works PR for inspiration on how to live a live a superficial, vapid life that is entirely subsidized by your family fortune. Your Sally Draper like appearance may trick people into thinking you're young and innocent. Because of your youthful looks, you've been using your parents' black AmEx's instead of fake IDs at bars since you were 13. You have the soul of Hannibal Lecter on the inside, and I love that about you.
[Photo via @mayflymoretz]