I'm looking for some advice / thoughts on a [platonic] relationship, with my childhood best friend from whom I have drifted apart. I feel significant guilt and/or sadness when I think of my friend from time to time. I guess this post is meant to help me get this off my chest, put it out there for others' thoughts and to answer a few questions that I have in regards to this relationship. A little background first:

Growing up I (27M) had a small posse of friends, kids who I would hang out with, sleepovers, video games, typical boy stuff. I didn't have as many friends as some kids as I was pretty shy and didn't play team sports but in any given year I had 3 or 4 pretty close friends who I would devote most of my attention to. Something that is important to note is, these friends were not friends with each other - that later made it hard to keep them all once we got older. One of these friends, let's call him Jack, was my one and only "best" friend, a blood brother of sorts. We were best friends from basically toddlerhood until mid-high school and even for the first couple years of college we would get together occasionally. He has since moved away across the country, while I have gotten a job in our state and still live within an hour of our hometown. Primarily, he is the one person (besides my two sisters I guess) who shared a common experience with me during my formative years. I would say that I was closer to him than I was to my closest sister, because we were the same age (vs. my sister who is 3 years younger - a big number when you're a kid). Part of my sadness and guilt is because in drifting apart I feel like I have lost a tangible connection to that world that he and I shared for so many years. I feel like I lost a family member.

Our moms met when we were babies as they were walking us around the neighborhood in strollers and from that point on we were thick as thieves, at least from my perspective (more on this later). We both had similar features and blonde hair and we were often mistaken for fraternal twins. Our personalities were very different though. Jack was disorderly, liked to run around, the kind of kid who was into Power Rangers (something of our time I suppose) and superhero comics. I was quiet, didn't (and still don't) like getting my hands dirty, was into model cars and board games. Those of who who are old or weird enough to get this reference, we were often compared to Felix and Oscar from The Odd Couple. Somehow though we were able to find common ground and got along well, but sometimes fought like brothers do.

As we got older, the differences in our personalities perhaps became more apparent. Jack's home situation was different than mine. His mom was bohemian, a single mom, into things that my parents viewed as "hippy dippy" but she was fun and always down for what she called an "adventure". Some of my best memories as a kid were manufactured by Jack's mom's crazy adventures. Jack's mom always rented a small apartment in the "downtown" area of our small city of 35,000 and went to a different elementary school. She was the kind of mom who would turn a blind eye and "let boys be boys". She would let us roam the mall by ourselves starting at 8 years old, a great treat (and something which I had to keep a secret from my mom as she didn't approve). Jack's dad was a typical blue collar guy of our town, worked in some sort of factory. He seemed like a nice guy, but was somewhat stoic in personality, or so it seemed, and I never really felt like Jack was as close to him as I was to my dad. Growing up I was told he had some issues with alcoholism and was a heavy smoker, so Jack's mom kept him at an arms-length distance. My parents on the other hand were a bit different. Both had minor white collar jobs, and we lived on the "nicer" side of town by the time I was 5 or 6 and my mom in particular is pretty uptight. My mom was / is a domineering figure. My parents drilled into me from a young age the "evils" of drugs, sex (and rock and roll, couldn't help myself) and the benefits of productivity and I followed their guidance to the letter. In hindsight I was a know it all, always trying to prove to myself (and probably to others) how I was smarter or better. This I could go into great length on (another post for another subreddit) but primarily was because of self-esteem issues, partly caused by my ineptness physically (sports, running...etc). I think I felt like the only way I could compete with my peers was intellectually.

When we were 12 Jack's dad died suddenly of a massive heart attack. I was definitely not emotionally mature enough to address this with him (and my parents really didn't do a good job of helping me address it either). I probably said, "I'm really sorry, are you ok?" and then moved on like it never happened. I have a vague memory once of him getting upset shortly after when I made mention of my dad in conversation, completely not thinking anything of it and definitely not purposely trying to upset him. Now as an adult I recognize that as a massive faux pas, but as an innocent 12 year old, I didn't think before I spoke. He acted like it really hurt him, and I feel like that incident might have permanently damaged our relationship. I was sort of flippant with the dad topic around him, because I expected him to seem really upset the first time I saw him after his father passed away, and he didn't. I guess in my naïveté I assumed he was ok.

I also recognize now that I took his relationship with me for granted. I remember thinking at some point when I was 10 or 11 that we would be like brothers forever and picturing us in our 60s sitting there on the floor playing xbox like we did for hours and hours. I think I started treating him more like a sibling that was stuck with me rather than a friend who has the choice to leave.

We went on vacation once when we were 13 or 14, my parents brought him with us, and I remember being a massive jerk to him about him breaking some stupid toy that I bought in the gift shop. We had a little spat in the hotel room that ended up in a bit of fisticuffs, and I remember my mom pulling me aside and telling me to appreciate him as a friend and apologize. That did shake me up a bit but I didn't know what to say or how to react (again I was a young kid and was sheltered by my parents, so perhaps didn't have the social skills that I should have had). We were both definitely spoiled brats that were used to getting whatever we wanted, but maybe moreso me because I wasn't exposed to any weirdness in my parents' relationship up to that point, while Jack was moved around a few times as a kid as his mom went from boyfriend to boyfriend and probably had to deal with more s**t from his parents.

A year after that, my parents went through a messy divorce. I was ok with it, but he was definitely not a supporting friend. That is when he started pulling back the most I feel, and when I was closest to a couple other friends who were very different.

As the years went on I suppose our common ground was slowly eroded. We both made other friends; friends who had more in common with our interests of the time. His were girls (he had "girlfriends" starting at age 12 or so, I didn't until college [not that I wasn't interested - nerd life]), working out, sports, weird music, skateboards. I was a stereotypical nerd into computers, board games, band, Model UN, weird stuff like that. I actually remember feeling quite a bit of resentment that he couldn't help me get a girlfriend like a bro should (plenty of girls liked and respected him and I felt like he could have pulled me into his crowd somewhat). Instead I felt pushed out. I know that's kid stuff, but I feel that it's relevant to help me frame how this relationship was. Towards Junior year of high school, it became what felt like a one-sided friendship. I became the only one who would try to arrange things, and he was often unavailable or would cancel at the last minute. When we would meet there would always be another friend with him unannounced, or his girlfriend (the one he had for most of high school clearly didn't enjoy me being around either). For better or worse (and maybe I'm the bad guy here feeling this way) but that made me feel like my company wasn't good enough anymore, like maybe he didn't find me interesting. Eventually I guess I stopped making an effort.

The last time I saw Jack in person was sometime in early 2013, probably 12 months after I'd last seen him deliberately (we went skiing I think, and had a good time). I saw him while driving through a parking lot. I rolled down my window, said "Hey!" and we chatted for a few minutes. He told me he was working at American Eagle (last I had known he was in college to be an english teacher so that took me aback and I really didn't know how to relate or what to say - I was focused on finding a white collar career at the time). Within 6 or 9 months of that time I learned from the grapevine that he had moved out of state. Since then we have each sent the other happy birthday texts and a few other messages, but no real interaction. In late 2019 I tried to arrange a meet-up in his home state (I was traveling to visit family and thought we could meet for a drink and he told me he had moved again to a different state). He did seem interested in meeting up and apologetic that the timing hadn't worked out better. He told me that if I'm ever in his new home, to let him know. For the record, if Jack has been home to my state in the last 7 years, he has not looked me up (and I'm sure he has been home at least once, as his grandmother passed away last year).

I'm not at all hurt by the fact that Jack is out there living his own life and doing his own thing, nor am I hurt by the fact that he made other friends. That's totally normal, and I've done the same thing. What hurts me now is that Jack doesn't seem to really care that we spent the majority of the first 15 years of our social lives together, like that time really doesn't have meaning to him.

For the record I do not feel this way with the vast majority of the friends I had over the years who came and went (with the exception of two - these probably deserve two other posts which I can go into detail on if there's interest). But even compared to those two, for some reason Jack holds a special place in my heart, sort of like how one might feel if a close cousin or sibling were to cut you out of his or her life. Also, please don't think this is a topic I think about a lot. I have a very good job, two college degrees, money in the bank, a girlfriend who might as well be my wife, and a nice house. I have friends new and old and close family. But for some reason the Jack question pops up in my head every now and then and really bothers me.

And so that leads me to these closing questions:

1.) Should I feel guilty, all these years later, about how our relationship played out?

2.) Should I feel "cut" out of his life in the same way that one would feel cut out of a family member's life if he or she did the same thing?

3.) Should I reach out to him? If so, should I reach out under the guise of "clearing the air" or should I just reach out to reconnect with an old friend?

Thank you for any and all feedback, and apologies for the length of this message. There is more detail I could have added but eliminated for the sake of length.