Elle's comment is based on how an employer would look at it... Your offense to her comment and own summary shows how much you have thought about reconnecting with this man. You really have to look at the whole picture not just your old skool crush but now your future with your job and also his track record. Would it be worth the road you travel? Don't kid yourself that you only want to help him, it's clear it runs deeper than that. Be honest with yourself it won't be plain sailing!