<human>: I have known this guy for 14 years, but we have been really close friends since freshman year of high school. We go to universities in different states, but we Skype every Sunday so we are still super close. 

We are now both back for the break and have plans to hang out quite a bit. We always fake flirt with each other, the over dramatic type. Anyways, I've always had a thing for him but I don't think he feels the same so I push my feelings back.

Four years ago I told him that I had used to like him, but he said he thinks I'm a great friend. He's never had a girlfriend so maybe he is just shy or scared. Things may have possibly change since then, so how should I go about bringing that up?

Condense the text into a few key points
<bot>: I've been friends with this guy a long time and I want to bring up being in a relationship but don't know how.