I remember as recently as eleventh grade, when I was in a career development class, that I wanted to work in a job where I would not have to deal much with people - certainly no jobs where there was a lot of interpersonal interaction. I certainly have been, and to a lesser extent nowadays, an introvert. Yes, people change.
I think my trying to be מקפיד (particular) to remember people's names in the spring of 2002, when I was an undergrad at YU and was playing basketball when a law student I knew was very good about calling people by their names. It struck me as I didn't and others seldom did, except the people they specifically knew. But what struck me about Richard, this law student, was that it was so... nice. Although people were nice to those, I found, in their own cliques, people often weren't particularly nice to others (that isn't to say that they were nasty or mean, though). He seemed to be indiscriminately nice, somehow, and that it was an aspect of כבוד הבריות (showing honor to others).
That following summer was my first (eventually, of three) summers staffing the international leadership programs of BBYO. I staffed a four-week program with over a hundred participants and a three-week program with about 150 participants (maybe more, but hopefully the figures aren't that significant). Having come off of an all-male yeshivah environment, having spent the previous fall in yeshivah in Israel, then the spring at YU, I didn't think it too appropriate to know all of the girls, so I didn't know all of the girls after that month, but I did a pretty good job of knowing the guys' names. I felt bad about not knowing all of their names, so for the next program, I made sure I got their names down - I actually did surprisingly well! From then on, I've been pretty good about getting peoples' names down.
Another two events are significant to the development of my sociability. The first of these two occurred in the fall of 2001, when I was in Israel. I had a dorm counselor who had two masters degrees and was pursuing a doctorate in psychology, I think (no bachelor's, though(!)), and was a fascinating guy and really enjoyed his Thursday night mishmar discourses, which were heavily infused with kabbalah or hasidus or something. Anyways, I had a few sessions with him, which were great, just talking with him. The latter part of that semester and, to some extent, the following semester at YU, I found it interesting to speak with other people. This remained until the second event, which were different discursive experiences, which mainly took place at the Hillel. I felt it sort of put me back into a more 'normal' and not 'interesting' mode of social intercourse.
However, over the past year, during my time both scholastically at YCT, and socially in the Heights/Mt. Sinai/young people crowd, my social skills have picked up, albeit with mixes of speaking of the metadiscourse within casual conversation, being sort of simple, along with the employment of other methods of discourse. Although it was slow last fall, from the spring, and especially through the summer, I have come to know a wide number of people here.
A couple of anecdotes from yesterday to share: at shul, I was going around, as per usual, meeting people and a RIETS guy who I know complimented me on my welcoming abilities, saying that I would make a good rabbi. 2) I was at a party last night and chatting with various people and twice (perhaps it was thrice(?)), people suggested that I go around and mingle - that maybe there would be someone for me. I found it amusing, as they were encouraging (no they were not trying to get rid of me (at least I hope not)) me, not that I was being antisocial, though, but in a way that seemed to say I had a certain proficiency with conversation.
Although I wouldn't say that I've gotten back to where I was a few years ago, I've realized it's not about regaining that sense, it's about progressing to incorporate what I learned then, as well as to try to live in the moment, and appreciate people.