Being a kid in the 80s and HS in the 90s was.. ok. There were definitely highs (loved video games and comics, surprise surprise I was a giant nerd) but being a geek before it was "cool" was kind of a drag. Of course I bonded together with a bunch of the other low-self-esteem outcasts at school, high school became MUCH MORE tolerable once we found each other. Burned a lot of time, making dumb jokes and bumming around town all the time. Working menial jobs just to get some scratch, but it was all fine. The future wasn't terribly exciting (my world view was extremely sheltered and small) but it was what it was.
Going to college IMMEDIATELY blew my eyes open, on the other hand. A little bit of freedom, finally, for my sheltered-ass-self - plus engaging in what was interesting to me (I was an art student) life went from "whatever" to "oh damn this is exciting" pretty quickly. I still had little to no game, but just being out and part of the world and left to my own devices was such a charge. Then from there to my early 20s, starting my career, moving on a whim to the exciting west coast/etc - it was all quite a rush..
But happy? Hard to say? I reflect back on the high school years and my nerdy friends, many of who I still talk to in a pretty diminished capacity, and maybe see once a year if I am lucky (when I am home visiting for a few days) - honestly those were some of the best times. Yeah we were all dorks and had nothing but each other back then, but now I cherish those memories and really miss the meat and potatoes of those days. Just hanging out and watching TV or strumming a guitar and going over our endless dumb, tasteless, raunchy, or just plain stupid in-jokes. Driving around the burbs late at night stealing people's recycling bins and what-not. Chilling out in my room and listening to a Monty Python CD and playing F-Zero endlessly. All this mundane stuff but I would pay any amount of money to have that be my life again, it feels like..
The past is what has made you what you are, good and bad. Best not to dwell on it too much, but also good to keep an eye on it and see where things are in your life now (as an older adult) and compare and contrast what was going on and "seemed so important at the time" vs what the priorities in life are like now (and shall be, down the road). You can always cherry pick stuff from the past (good and bad) but overall, it's just THE PAST. Get on with things today, and hopefully they will lead to things being better tomorrow. Or so I am hopeful, they will be..