Should I tell this guy I like him? If so how??? IF YOU HELP I WILL ANSWER ONE OF YOURS!?

[Tori]

I really like this guy, and I have since November last year. We used to talk a fair bit for hours(Note: this is on Facebook and I always started the conversations, in saying that he would ask questions to keep the convo flowing).
~Go to my first question for more info~(Btw he only opened up that message last week..)
Anyway we just started back at school last week and at first we didn't really make that much eye contact but now we catch eye contact a lot and when we do we always smile at each other. I really want to talk to him(Ive done that a little in person: 2-3 times haha, just not online like Facebook,snapchat ect.) I just don't want to be the one to start the convo because everyone said to wait for him to message me first(see first question) I want to find a way to get him to message me first, to give him a bit of courage but idk what to do.. I've tried posting on my snapchat story "someone talk to me? " and a few other things. Should I tell him I like him? If so how?
Help?!?