Does he like me? Should I make the first move?

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Agreed. Just ask the SOB for coffee and stop being so damn manipulative. He deserves better.

See if this advice was applied to a man, he'd be considered a "nice guy" and secretly a sociopath for doing this, and being totally manipulative and terrible for not telling his feelings right away.

The thing is, a time will come when you will have to share how you feel for a relationship to happen. Or else you'll be in perpetual limbo forever. And regarding ruining the friendship. You know what else ruins friendships? Being dishonest, in this case by omission. You can't hang out with someone you can't be open with. So your gambles can turn out like this. Eventually lose him as a friend due to not being able to be honest with him. Eventually lose him as a friend due to him not wanting to be romantically involved with you. Or winning. Of course you could also tell him and everything remains the same. As hard as it is, not telling someone how you feel will only lead you to a life of misery and regret that you'll have to face everyday. I still deal with mine from not telling someone how I felt who later got married. So you can give it a week to sleep on or whatever, but in the end these are your options.

I worked up the courage to text him left now and I'm so glad I did. I'm sure he likes me back. I'm going to ask him out next time I see him in person. Wish me luck.