Most Helpful Guy
It is a delicate situation but if you think you have feelings for him go for it. If you don't have feelings back out now you will only hurt him in long run.
Most Helpful Girl
Not bad at all! Just try not to overanalyse things. (I'm not sure if you are, but what I'm saying is: Go with the flow, if it goes well then yeah, that's awesome! If not then go back to being friends.)
Good luck to you guys :)