How to handle a guy who loves the chase?

You might know the plot :). We're close friends, classmates and around 18. We share the same social circle and there's always been this tension between us. We are both quite reserved and we always want what we can't have. He let down his guards and we are honest with each other, causing us to respect each other a lot.

He has had a huge crush on this girl who strung him along for several months before we met. I would know that he has cried himself to sleep some nights. It was hard to see him suffer, knowing that even a hug would make me his rebound.

A month later, he would sometimes sneak in my window and we would listen to music and talk all night about dreams, ambitions and stuff. We kissed and cuddled a bit but I did not want to take it further as it was probably nothing serious and I wouldn't risk our friendship, even though I am attracted to him as well. I also don't want to pour my feelings all over him. I did need some sort of clarification though, since we are classmates and someone's gonna get hurt along the road. He told me not to get my expectations too high and I told him "cool - let's go back to friendzone" as he only wanted something casual and I wanted something stable.

Then I stopped contacting him, answering him politely and short when necessary. He is my friend after all. I could tell he wasn't over his former crush. Yet, as soon as he realised his 'competition' and my lack of interest, he was immediately pursuing me more aggresively. He would text me all night, notice my location through messenger and ask me about my plans. He even tried to call me in the middle of the night when I did not answer his desperate attempts. What am I to do with him? After all, he asked for this treatment himself.

I know how we both love the chase.. Would we ever be able to meet halfway down the road?
How to handle a guy who loves the chase?
Add Opinion