Right guy, wrong timing?

Today my parents went to the 40th birthday party of a guy my dad used to work with, and who I met for the first time as a teenager. He was a nice guy, not too bad looking, and one of few people my dad associated with that I would actually carry on a conversation with. A few years ago my dad mentioned that he believed this person liked me. I thought then, just as I think now, that it is really too bad that I didn't know that, and that even if I had, it might not have made any difference because I was a teenager when I met him. Despite the fact that there was only a 3-year gap in our ages, I figured there is no way in the world my father would let me date someone who was technically an adult. Nor did I want such an occurrence to potentially harm their working relationship. This man moved up in the company and now has a pretty stable job making decent income.

I can't help but feel like maybe I missed the boat, all due to a silly technicality. While that 3-year gap might have made a difference way back then, it makes absolutely no difference now. Was the significance of this age difference then a necessary roadblock to keep a relationship that shouldn't happen from happening? Or was it a silly technicality that may have thwarted a potentially good relationship? Given my track record for relationships that clearly shouldn't have happened, I find it hard to believe that this relationship would have been more toxic than those I did have. On the contrary, I think this could have been a good thing, and were it not for the fact that I was not feeling well this evening, I might have asked if the man was by any chance single. Perhaps I shall keep this in mind when my own daughter turns 16 or 17 years old, should she encounter a similar predicament.