Since you really don’t want to become a creepy guy, I think it’s worth reiterating that what you’re describing isn’t a game. It’s just what all non-creepy people do. My wife is very introverted and she has a much smaller circle of friends than me who she feels the need to see a lot less frequently than I want to see my own friends. She still has one though. In short - great goal. Glad you got the message. It would behoove to not think of it as a game or a strategy.
Start going to social events with your one friend. Tell him you really want to have more friends and ask him to help you work on it by also being friendly at these events.
By the way, in my experience making new friend out of an acquaintance doesn’t necessarily have a lot to do with having deep conversations. I’ve found it’s more about one of you suggesting that you two actually do something together, rather than just running into one another or being friends of a mutual friend. Once you hang out a few times, you’re friends.
If I meet someone new I’ve never found myself thinking, “Is this person capable of deep emotional conversation?”, I find myself thinking “Is this person fun and enjoyable to spend time with?”
You can’t suppress your emotions. You’re 16. 30 is almost 100% of your current life away from you. I think you need to work on accepting that the way you’re thinking is actively harming your objective and making it ever so slightly more likely that the thing you are obsessing about will come to be.
Honestly it’s really rare to be that old and have no romantic success. But obsessing over it and acting really desperate and creepy has got to be one of the best ways to help ensure it does happen.