That is a very interesting question for both of them as it is really a conundrum. They have it down to a couple of possibilities.
Ray recalls of a time where Bobby was teaching a Newbie Dance Class at the Dance Shack. Surprisingly, Bobby did not embarrass himself and taught the class as a proper instructor. He was very serious about teaching. A very strict instructor. Of course, this is false. He was ridiculous in his teaching methodology. Sadly, his memory fails him and he does not recall this moment, as well as what he ate for lunch today.
There was also the many times they danced at the Volstead and in Lindy practice at the Dance Shack. This evolved into hanging out with our friends in the dance community and us hanging out more together.
Another time we discovered was before both of them realized! Apparently, we had met and danced together at the Volstead when both Ray and Bobby first danced at the Volstead. This was figured out as it was one of the only moments a substitute instructor was teaching at the Volstead.
So when did we first meet? Who really knows? :P