It's been a long time since I have been actively involved in this sort of issue, as I am now almost 60 and have been happily married almost 30 years and have three children. But when I was a young and certainly nerdy guy who went on to get a B.S. degree in physics and graduate degrees in engineering, I was completely clueless when it came to the opposite sex and very difficult to communicate with--unless you just wanted to ask me about homework.
When I was in high school and middle school, girls did sometimes take an interest in me. I had a precociously ironic sense of humor and people laughed at my jokes in class. I was also a good artist and girls in art glass admired my artwork. Popular girls would sometimes attempt to strike up a conversation with me, or ask me to attend some event after school so they would have somebody to talk to. But I was too preoccupied to studying to pay attention to these girls, because in the earlier grades I had done pretty badly in school. I resolved to do better, and was afraid that I would end up as a homeless person if I did not get better organized. I probably had a form of ADHD, but that was back when nobody knew about that kind of thing. When I now read recommendations regarding what people with ADHD should do to cope with their condition, I find that I did most of those things as I tried to better focus my mind. In particular, I tried to avoid any kind of distraction, so starting in 8th grade and all through high school I spent all my time--from the moment I got off the bus until the time I went bed (except for dinner) doing homework and studying. I should also note that because I went to a little country high school, I was also worried about the much smarted and well prepared students that I would have to compete with in college.
Finally, in 11th grade I went out with the one girl who I found truly amazing--a very refined and intelligent girl who I later learned was the daughter of professors at the local college. Our date--which involved going to a movie--proved to be extremely awkward in that I was unable to carry on any kind of normal conversation--as I just sort of randomly said what ever came into my head. My efforts to get this girl to go on a second date proved futile, so I was left with nothing more than a feeling that this whole dating thing was hardly worth the trouble. So for almost the rest of high school I really made no significant effort to go out with anybody.
High school would have continued to be socially uneventful for me if it had not been for one random event that changed everything. At a National Honor Society function during almost the last month of senior year, I reluctantly followed my best friend to a table in the lunchroom where the girl who I had unsuccessfully pursued was sitting. I was somewhat embarrassed to find myself sitting right across from her, as I had hardly spoken to her since I had given up on pursuing her. So out of a need to dispel the tension that I felt, I started a monologue on a topic that I was pretty sure nobody else would have anything to say about--Einstein's Theory of Special Relativity--a topic way too advanced for our high school physics class--and which I had studied intensely on my own from a college physics book. To my surprise, however, I had hardly begun my lecture before a cute 11th grade girl who I had not even noticed interrupted me with a number of interesting questions. The conversation that followed was unbelievable. I had never had a deep philosophical conversation like this with anybody before. So I asked this intelligent and outgoing girl out and we dated for about a year.
From my experience with the girl who responded to my lecture on special relativity, I came to realize that dating could actually be worthwhile and that I should seek out girls with whom I could have an interesting conversation. And so if I happened to be having an interesting conversation with a girl, I should ask her out. But this approach was really more difficult for me than it sounds. In high school, or perhaps even a small college, you can easily find out who somebody is--even without asking them directly. At the large universities that I attended, if I met some girl by chance who was not in my class, I would have to ask her full name or phone number if I wanted to see her her again--and I would have to transition the conversation for this purpose. This was a hard thing for me to learn to do--and I was probably not able to make this sort of transition in a conversation until I was 25. So for a young nerdy guy like me the girl would have a better chance in she would at least give me her full name so that I could at least look her up in the university directory.
By the time I met my wife (another daughter of college professors) at age 28, I was able to make this sort of transition in a conversation, and ask her phone number--and even schedule the date--as a contiguous part of the initial interesting conversation.