Well you already mentioned that he is your friend, right? So when you approach him, be casual. Start talking about casual stuff like how his or your day was, what you did/going to do over the weekend, etc., but be a little flirty. Then when the opportunity arises (like you're talking about your favorite restaurant or that one place you've always wanted to go to that's not out of town), ask him if he wants to do something with you. Not you and a friend, not you and his friend, but JUST you. Don't feel awkward about it or else it'll be awkward. Just pretend it's like hanging out. No biggie, right?
If he says no, don't get discouraged. There is always next time. If he says yes, then hooray! During your date/hang out, continue to be flirty. Don't drop anything too obvious that shouts "I have a crush on you!!!" but don't make it seem like you guys are JUST FRIENDS. Find that balance. And at the end of it, say something like "that was fun, I hope we can do this again" so he knows that you want to hang out with him in the future. Over time, this could potentially develop into something quite beautiful. Just be patient and don't rush into it or else it might scare him off. And most importantly, have fun. If you two aren't having a good time, there won't be a next time.
I hope things go well for you!!!
