Looking for advice on talking to someone

Hey all. So I'll start by saying I am 25 and have never been in a relationship. 6 months ago I was talking with an old friend whos a few years younger and we ended up getting drinks and heading back to his place and ended up fooling around.I asked if he wanted to hang out more the next day when he said he was getting serious with another and didn't want to ruin it which was fine.Fast forward to a few days ago where he came back from school for the break and we started messaging on grindr and he asked for my number as he had lost it.I really like him. I ended up coming out to my sister last night as the thought of being with him gave me the courage to come out and accept who I am.If it were you would you take the initiative and be up front about how you feel, or just go with the flow and casually text until it seems appropriate? Thanks