You and Olivia are walking hand in hand when you ask her out.

"Oh, I'm sorry, my love! It's just... I'm not feeling very well. Can you give me some money to go to the pharmacy? And a very expensive pill." It was obviously an excuse, she wants to go to a pool party with some handsome and athletic guys. She never asks you out because she's embarrassed to go out with you because you're a nerd. "You don't mind, do you, my love?" She asked with a fake smile, but with disdain and disgust inside.