I had an experience like the one mentioned, where I was more of the 'nerd' type and the 1-2 teens in my congregation were more hip than I was. They were nice enough to let me tag along, though, but I always felt like a 'fifth wheel' kind of thing. (Note: this was the mid to late 80s)
My mother was actually helpful with this, to a point... since my family went back a couple generations in JWs, we were kind of looked up to by the more spiritually-minded people. So mom would try to hold little get-togethers at our house, to try and help me and some of the other socially-challenged teens (and keep them from worldly alternatives, etc). Once we had a lip-synching 'party' with about a dozen or two kids (and the parents who wanted to attend), good times.
I do remember getting my hopes up once... senior prom was NEVER an option, of course. But that year a bunch of parents wanted to try and have an alternative within the organization so the kids wouldn't be quite as left out by not going. The word spread through several congregations in neighboring cities that a school auditorium was available, and there was going to be a prom-like gathering for the teens.. dress up formally as possible, a musically-inclined friend was going to play some tunes and had 'acceptable' music to be played as well... even as incredibly shy as I was, this was defintely something I was looking forward to this for WEEKS (especially since there was a super-cutie young sister I had met, and had hoped to talk to some more, heh).
....but the weekend before it was going to happen, there was some talks about avoiding 'large gatherings', a few people had crisis of conscience issues, and it was cancelled. sigh
It was a little difficult for me because there were higher expectations. Everyone seemed to think I'd be a regular pioneer and probably Bethel bound when I got out of school. It was kind of fun getting privleges within the congregation... carrying the microphones, giving talks, reading the Watchtower aloud on Sunday... but deep down it always felt like having to settle for what I could get, since I couldn't have what I really wanted, lol
Personally, I was already tempted by worldly influences, a bit of a rebel despite being from a 'good family'... I'd listen to worldy pop music, try to catch TV shows when mom wasn't around, etc. I liked a couple of friends I made who were more open-minded, being able to escape and play video games, listen to whatever was on the radio without changing the station because a 'bad song' came on, lol Always had crushes on girls but was too shy to talk to them, and you weren't supposed to be all that friendly anyway (since it was WAY too young to be thinking about marriage, so any considerations of dating were not acceptable). At best, I could hope for a group outing that included the pretty young lady I was pining for, and maybe getting the courage to talk to her, lol
Funny, I could talk to complete strangers in service, deal with 'conversation stoppers', do informal street work... but talk to the happy brunette who was my age? Yikes! haha
Ah well. In the end, like any other teenager.. I guess I just tried to make the best of it, do what I could, and find the enjoyment that was there... and along the way, had a lot of unusual experiences! :)
(hmm, that was a lot more than I thought I had to say,haha)