I know i'm thinking on a grander scale but I would be more worried about you not liking him or how he supports, comments, makes you feel then worried about how a relative stranger (even if he is cute) feels about your WOE.

Maybe it is just a sore spot in my history with men but this is YOUR life and you should chose people to be around that you can be honest and true to yourself with.

A BF or eventual partner should be someone you are better with... then when you were alone.