Missed Opportunities

So, this is my first time posting in this forum. When I was younger (school, college), I was very shy and did not date or have a boyfriend. I'm 32 now and am much less shy and feel ready to date. I had two experiences where guys seemed to be interested, looking back. In high school, there was a guy who was a bit "flirty" and when we were assigned to work together, wanted to get together outside of school to work on a project which probably wasn't necessary :) The fact that we didn't really need to work on this project outside of school is what made me think he was interested. He was also always super complimentary toward me. I was so shy though that I said no to getting together (which I realize now seems like rejection). It's hard to explain, but it was the way he smiled at me and interacted with me that was completely different than how he interacted with other people.

In college, there was a guy who lived in my dorm who showed up next to me at various events on campus and seemed to make it a point to be around me. In college, though, I could barely hold a conversation with a guy. I was so shy that I was completely oblivious to all this when I was younger.

Fast forward to the present: when I was looking up doctors online, I stumbled across HS guy's name (he's a doctor now). He has amazing reviews and sounds like the same great guy I knew. He does not seem to be married or in a relationship. It weighs on my mind that I did not reciprocate interest and missed out on good guys. I have thought about friending HS guy on Facebook but it feels awkward (what if he doesn't remember me? what if he thinks it's weird I'm friending him?). At the same time, I just remember feeling so drawn to him and how he was so nice. He was honestly just not like any other guy I've met before and it just makes me feel sad that my shyness ultimately held me back. I don't want to "live in the past" so to speak, it's something that weighs on my mind. Maybe nothing would have come from it and we would have just been friends. But there's a part of me that can't help wondering "what if?" I don't know if this sounds silly or crazy, but I am kicking myself now for all these missed opportunities. Now that I'm ready and really want to date, I'm not meeting anyone and feel like I'm "behind" and am unsure where to start w/ dating.

I'm just so afraid of ending up alone and never meeting anyone.

It's fine to friend old school mates and college alumni on Fb. However to date, get on dating apps.

I'm 32 now and am much less shy and feel ready to date. I have thought about friending HS guy on Facebook but it feels awkward.