Blame it on my inner 12-year-old, but I couldn't resist talking about the amazing relationships Rory has on Gilmore Girls. They all have one thing in common: challenging each other to go outside of their comfort zones. Dean is her first love, her first heartbreak, and her first sexual partner. His controlling behaviour also forces Rory to be more independent (sorry, controlling is not cute). Jess is the bad boy, showing Rory the exciting, passionate side of life, then later encourageing her to go back to Yale to fulfil the future she's always wanted. Finally, Logan pushes her in ways she never experienced before. He gets her to join a secret society, teaches her the challenges of dating someone long-distance, encourages her to think in different ways and try new things, and proposes to her. She ends up declining, but the gesture helps her realise she wants to work hard to jump-start her career that she's worked for her entire life.