LOL -- no I have never hit on anyone as I am a big chicken. However, if you did ask the person out, I am sure it would bother you down the road if a relationship ensued. For you -- it may signal something deeper ...... however, you should give it a try. Perhaps this person has never been introduced to this lifestyle in a way that has been motivational and supportive.
If this person is cute, smart, funny and interesting -- there are SOOO very few of those out there!!! I say put blinders on for now and take a risk....worse case scenario, it does not work out but at least you have developed a friendship.