Yeah, you should! Some chances never come again! For example, if you find soemthing he lieks like you do, start a mini conversation like with a compliment or a question. Or try to get involved with the same things\groups like him. Or,(xD) just talk to him. It´s better though to be around 95 percent sure he likes you back before you tell him, it could be rlly embarrasing. Well, it depends, sometimes there isn´t rlly a plan how to do it, sometimes you just have to make one up as you go along. Well, good luck! =)
i had the same problem two months ago but the boy i liked was in my bus and i known him from 3 years.
so, i think that you have to confess to him either by talking to him or by giving him a letter like i did :)
but the most important thing is : DON'T LOOSE FAITH!!
because i thought that the guy that i've confessed to him hated me but he actually liked me !!
so, yes tell him :)
talk to him more! if you really like him and you think he likes you give him some clues. you can even sometimes tell it to him straight. if he says something funny, tell him he's funny! if you just feel like you enjoy spending time with him, tell him you like when he's around. go for it! yolo!