I like him more than a friend. What should i do?

This summer me and my friend Sammy have been hanging out with one of our neighbors, Jake. Jake started asking us to come over with his senior friends to hang out. Me and Sammy are sophmores and all Jakes friends are seniors. Then one of Jakes friends, Chris started to call me alot making prank phone calls. He also took my quiz on facebook 13 times in a row! I started to like Chris. He is very sweet and funny. For my birthday, he gave me a gift card to hollister. One time he also gave me a ride home from school. He was going over to Jakes house and dropped me off at my house! What should i do to take it a step further with out asking him out?