Clearly, you are a caring and invoved parent, and I apologize if I misconstrued joking allusions to your frustrations with not getting laid enough in high school as creepy (it’s not like I can’t relate to the attractiveness of teenage girls. As a comedian once said, “if a girl has a nice ass, she probably works out. If she has a great ass, then she’s probably 16.” Now who is the creepy one?!)
Still, I would try and avoid being too caught up in the social highs and lows of your son. If, as you say, he has so much going for him, then he’ll be fine. Maybe he won’t have as many sexual conquests as other guys, but that need not prevent him from being a well-rounded, successful individual. Indeed, the time he is devoting to interests like acting are only going to make him a more interesting person, and his “struggles” with social activities are going to make him more empathetic when encountering other people who don’t always fit in. These are important qualities.
I say this not as a parent, but as a (relatively) well adjusted 29 year old adult who was never very involved in all of the cliques that predominate teenage life. I was only a few months shy of 18 before I even held a girl’s hand (granted, I lost my virginity to her a month or so later, but it took a while before I got the ball rolling). Even now, I’m not the type who always has a girlfriend.
Still, I’m happy, productive, and am making successful inroads on a promising career. I know I am an eligible bachelor, so I’m not too stressed about who is available. I’ve seen a lot of “popular” kids, OTOH, who are already married, with kids, and not too happy about those choices in life. We all progress at different paces, and it may be to your son’s advantage that his pace is different then the mainstream.
If you make it seem like a big deal, however, he might get worried about being different. He’ll make clumsy awkward advances to try and live up to your standard, even if you are only trying to help him realize his potential. He may get bogged down in the need to “score”, and his desperation could led him to gravitate towards people or situations that are not particularly healthy or responsible (the best way to make a ton of friends as a teenager in a short amount of time? Sadly, one answer is to start smoking pot).
So, IMHO, just chill. If he asks you for advice, tell him how you met his mother (surely, there was some suaveness to your experience). But don’t feel like you need to proffer unsolicited techniques, even if delivered with utmost sincerity or caring. He’s a good kid; you’ve already determined that. So rest assured that his good qualities will become apparent to the women around him in the time frame that is appropriate to him.