Currently trying to decide whether or not to tell this dude I have feelings for him. Thing is, I don't know whether he feels the same or even a little tiny bit the same. It's risky cause I don't want to scare him away cause I've told him too soon...
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I like it very much when a girl is clear about having feelings for me. In the instance that I were told this by a girl who had not interested me in the past, I would still oblige her to try to get to know her better - I have had better experiences in pairings where the woman was the pursuer for the greater confidence in that she's interested. The forthcoming nature of this would also also be refreshing - what tends to scare me away is too much thought for too little action: if I suspect that a girl is pursuing me and she doesn't do so openly.
You might do well to try another phrasing than 'feelings for you'. One that pangs less of the suggestion that someone thinks they love you after observing you from afar (more likely to scare) would be 'I'm interested in you', followed by 'I'd like to get to know you better'. Preferably, thereafter, spend time in private but don't call the engagements dates - that formal context has scared me away from every relationship so-attempted.1