Friendship Generations & ‘Best’ Friends
Have your friendships grown and evolved as you have?
This is something I’ve been reflecting on a lot in recent times, in part because I’ve felt something is missing.
I did an informal poll on my Facebook page, asking how many people are still actively in contact with someone they were in grade school with. To my surprise, each of the five people who responded said that yes, they were.
I think there are a few factors to consider here. For example — I am neurodivergent. In fact — doubly so — both Autistic and ADHD. I did not realize these things until well into my adult life, so it would make sense that I struggled to establish and maintain strong social connections in my youth and prior to my diagnosis.
And not for lack of trying. It was incredibly frustrating at times to try to connect with people, and have it not work, and just not understand why. Now I can’t throw a stone without hitting another neurodivergent person.
I know when Facebook first became open to everyone and started to become ubiquitous to my generation, you would often rapidly accumulate ‘friends’, but not have deep connections with as many of them.
The people that I knew who actively went out and participated in ‘night life’ social events (often past my bedtime) seemed to have richer and stronger connections, and had friends they seemed to talk to just about daily. I always wanted that but it felt inaccessible.
Of course we all know that your number of Facebook friends doesn’t actually mean anything concrete. Some people have 50 but they’re all quality. Some people have 2,000.
I’ve heard that studies say we are only really capable of maintaining meaningful relationships with up to 100 people. Many of us know lots more than that. I have nearly 1,200 followers on Instagram and I sure as heck don’t know even 10% of them all that well.
Everyone is busy and/or depressed which makes it hard to initiate a lot of social contact. So we can become more passive and isolated.
There’s also the question of what defines a ‘friend’? Does it have to be someone we still actively talk to on a regular basis? Or just someone we are friendly with. Like if we bump into each other, could it be ‘like old times’ and we chat for 15 minutes? The whole ‘nice to catch up with you!’ thing?
For the purposes of this article, I’m using the definition of ‘still actively talk to’, which shrinks the margins. But that feels like the more meaningful definition.
I decided to do an experiment.
Both for self reflection as well as to see what insights it might bring to my readers. I decided to reflect back on the many ‘chapters’ (or generations) of my life, and ponder the connections that were there or that I tried to establish, and trace connections forward.
I am happy to say that at this point in my life, I know lots of wonderful people. Many people who have told me they appreciate knowing me/having me in their lives. It’s certainly been a shift of change from my youth.
First ‘Chapter’— Grade School (Grades 1–8)
Most people have at least one friend in grade school. I had three at school and one from the street I lived on who went to a different school. There were two kids that I played hockey or video games with, one I just hung out with, and the final one was a girl who had a crush on me but I was oblivious for several years.
I am no longer in touch with any of these people. One of them ended up becoming a bully. I grew apart from the second, and the third one we had a really awkward moment where I unintentionally made her cry and we haven’t spoken since.
Friends gained in this generation: 4
Friends left from this generation: 0
Second Chapter— High School (Grades 9–13)
This was the first of several times when I genuinely thought a fresh new start would allow me to shed being ‘uncool’ and gain a group of new friends. And I did gain new friends… but I also still ended up being uncool and being teased a lot. Because I was awkward.
To add insult to injury, once in High School another girl had transferred to the school as well and she had gone to school with my cousin before who apparently was also very awkward and uncool. So now I was the new kid but this other new kid came in and blew it up for me by confirming that my family was just like that.
Also, since I lived right across the street from school I never stayed at school for lunch. I always came home and watched TV or played on the computer. So I was not actively building a social skill and was almost certainly missing out on opportunities to make new friends and deeper connections. I was just tired of being teased and being at school meant I was at risk of teasing.
Through high school I had more than 4 friends, but not by a wide margin.
And even a couple of my friends made fun of me because I was really, really not quick-witted. But I did not yet know that I was autistic.
I ended up making one friend at another school through his girlfriend who was in my programming class. They later had a really messy breakup and I had more in common with him so we stayed friends. We talk semi often these days but we are still friends.
Friends gained in this generation: at least 10
Friends left from this generation: 1
Third Chapter— College (Round One) and Adjacent
High School, wash, rinse, repeat.
I made some new friends, but my undiagnosed autism and growing frustrations with sucking at social interactions were not helping me.
I became an elitist in college, and as you may know if there are any such people in your family or social circles — elitists tend to be annoying if not insufferable. Elitism is passion that took a turn for the dark side and hooked up with some bad ego. But I was also only 19 and when you’re that young you still mostly don’t know your own rear-end from a hole in the ground.
I honestly don’t remember a ton about this chapter of my life, and not because I was drinking a lot or doing drugs. It was just very uneventful and I didn’t do much outside of class besides live on the computer.
Friends gained in this generation: a few
Friends left from this generation: 0
Fourth Chapter— College (Round Two) and Adjacent
This period started 3 years after the last. I dropped out of my original program (because reasons), took a year to work and ‘figure things out’, and went back for a new program.
Yet again, a whole new cohort of classmates, a new chance to make a good impression. I didn’t even want to be ‘popular’ anymore, I just wanted to be more liked. Popularity was clearly not in the cards for me.
I was now 22 years old, and thankfully by this point, I was at least as mature as (if not slightly more mature than) most of my classmates, many of whom were in their first year of college.
I recall at this time being very engrossed in my creative projects — namely the solo music record I was writing/recording.
I had been in the working world for a few years, I was now independently producing projects, and for school my focus was ‘get the assignment done so I can get back to my own stuff’. ie I wasn’t trying all that hard to make friends.
I had adjusted into being sociable/friends with people while sharing an environment (work, classroom, study hall), but outside of that I just did my thing.
This was a common theme as you can see.
Socializing never came easy to me and was usually frustrating. Working on projects independently was comparatively easy, fun, and rarely disappointing. But I was also missing out on so many opportunities and it would come back to bite me.
I think this was also the period where I really started to slip into the ‘please validate me’ phase of my life. This phase would last for about a decade.
Each time I had tried to smoothly make new friends, it would seem okay at first but eventually it would fizzle, and I took that personally. So eventually I wanted and needed reassurance that I was a good person worth being friends with because I felt like I was really failing to achieve that basic human metric. It’s not that I thought I was a bad person, I was honestly just confused why me as a person just didn’t seem to stick with people for long.
I don’t feel like I ever really even made a strong friend connection with anyone in this time. It was all convenience of social contact (work, class). I made friends with a few people on Facebook but never really kept in touch.
I made one friend through a band I was briefly in and remaining in contact with her until just last year (2021) when she chose to end that due to what I believe was a misunderstanding.
Friends gained in this generation: a few
Friends left from this generation: 0 (almost 1)
Fifth Chapter— First Few Yrs After Moving To Toronto & College Round 3 (2009–2012)
Finally moving to a new city — a much bigger city with many more social groupings — presented more opportunities than I could shake a stick at.
I was now 25. This was the point when I felt like I truly began to socially develop, as I had realized I was missing a lot of opportunities (and dealing with a lot of loneliness) because I just wasn’t good at talking to people. So I began to really push myself to try and change that.
I moved to Toronto both to be closer to the job I’d managed to secure, but also because I had felt like I was stagnating in my hometown (and as it turned out, I was very right).
This was the period during which I finally got diagnosed which was a game-changer. It didn’t reverse my fortunes overnight but it helped kickstart the process of me being able to seek better solutions to my struggles.
I began meeting so many new people socially and usually got to meet people in context of activities I liked which worked more in my favour. It was better than being trapped at work or in a class.
I was able to be passionate (but not as much in an elitist way) and was able to begin learning more social scripts to begin to mask my autism more.
People liked me because I was genuine, and I ended up meeting a lot of other people who were also awkward (many of whom would also turn out to be neurodivergent as well).
This was where the tide began to change.
I went to weekly board gaming nights. And made some friends of convenience there.
I spent about a year dabbling in the local kink and fetish community which exposed me to new activities, interests, and people. It definitely opened my mind more and led to some growth. (Side note: the overlap between board gamers and kinky people is practically a circle.)
I was meeting people through dating apps and becoming friends with some of them. This was really where I began to experience the phenomenon of getting along well with a lot of people, but rarely experiencing that ever important spark. It was still overall an improvement. I was learning.
I didn’t really make any new friends in college for the 3rd time because I was very much focused on just getting the work done and graduating. At this point I was a solid 10 years older than most of my classmates and didn’t relate to hardly any of them in any meaningful way.
I made most of my new friends independently from going out to social events based around things I liked.
Friends gained in this generation: Many
Friends left from this generation: Unsure of exact figure but I would say at least 10–20.
Sixth Chapter — Entrepreneur Journey Phase One (2013–2016)
Once I completed my 3rd round of college, I knew I didn’t want to be in that field forever (but it was good enough for now). I began to more seriously explore trying to start some kind of businesses from my interests.
I went to a lot of networking events in this time, but not many meaningful connections resulted. I was brand new to the world of entrepreneurship and as such I wasn’t very good. Add in that I was still learning how to not be socially awkward and it’s not super surprising.
A lot of the people I met in my first few years in Toronto ended up being my social anchors through this time. However, at the time I am writing this article, many of them have faded into the background and we only speak on rarer occasions now, if at all. But not everyone is meant to stay in your life forever.
Admittedly it is also harder to remember all the people I became ‘friends’ with in a period of time that was a decade or more ago.
Friends gained in this generation: Some
Friends left from this generation: A few.
Seventh Chapter — Gender Transition and Entrepreneur Journey Phase Two (2018–Mid 2021)
Somewhat like the undiagnosed autism being a persistent stick in my spokes for so many years, subconscious gender dysphoria took over on that in the decade since the autism diagnosis.
In looking back the signs are much more obvious.
But in making the choice to transition, it caused another reset. For a year and a half I was mostly only talking to other trans people. And then coming out the other side I needed to make new friends who were open minded and supportive. And I have.
At least by this point I was a lot more comfortable talking, was a lot less socially awkward, and was a lot more self-confident. A decade late maybe, but better late than never!
I had several ‘resets’ over my life that I failed to capitalize on until more recently.
I realized something, apart from this exercise but bolstered by it. I realized that I am someone who has consistently grown and evolved, and as such it makes sense that not all connections would persist. We grow out of some people and grow into new ones.
Friends gained in this generation: Many
Friends left from this generation: Several
Chapter Eight—Making New Friends And Not Adding Them On Facebook (Mid 2021-Present)
This is a new realm for me.
In the past there was often an eagerness about adding new friends on Facebook if you hit it off with them. But everyone is kind of tired of Facebook and the algorithm literally isn’t programmed to foster or encourage positive connection.
More and more younger people are spending less time on Facebook, if not quitting it altogether. Many millennials are still on it, but grudgingly. But nowadays I definitely don’t find people as eager to say ‘add me on Facebook!’. They’re more likely to ask if you’re on Instagram, Tiktok, Discord, or possibly Twitter.
I think that speaks to the evolution I mentioned earlier. We’ve come to realize that Facebook is kind of like an old friend turned acquaintance that we’ve mostly grown out of.
We’ve gone back to texting, or to platforms where we are more active and feel more in control. I’ve heard people say that Instagram has the least ‘toxicity’ of all the main platforms which is why many prefer it now.
It wasn’t on purpose, but I’ve made some new friends in the last 6 months and we either chat by text, by Instagram DM, by Discord DM, by FB messenger, or by Signal. But we never officially added each other as FB friends. We just talk.
It feels kind of like the old days of chatting with friends (old and new) on the phone or via ICQ or MSN Messenger or the like. There was MySpace and message boards but it was a little different. So you just talked and got to know people, and what was going on in their lives. What a novel concept!
That’s what Facebook is supposed to do, but it doesn’t anymore.
At first it was challenging because you have to manage this relationship completely manually. Like back before we got lazy from the ‘convenience’ of Facebook. But as I’ve gotten used to it, it’s been kind of refreshing honestly.
Friends gained in this generation: About 20 or so
Friends left from this generation: All of them (so far)
If I think about it now — the people I think most fondly of and enjoy the company of the most — are people I’ve met since moving to Toronto and getting my diagnosis. Mostly fellow neurodivergent nerds and a few neurotypicals with stellar personalities and kind hearts. People who are genuine, who care, who are great allies, and who appreciate being able to share in what they enjoy with others.
I am tempted to say that it would have really helped if I could have been diagnosed a decade sooner, but my nephew is Autistic and was diagnosed before he even turned 10, and despite the help he has received, he too is struggling a lot. So earlier diagnosis isn’t necessarily the true solution. Either way you still have to learn to mask and talk to people.
I admit I am a little hung up on the fact that I’ve never had that ‘Best Friend’ that many of my friends have. It feels like a failure of sorts. But I do have friends who are there for me, who care about me, who would let me crash on their couch if my life fell apart. I have lots of ‘chosen family’.
I’m certainly not short on what matters.
Perhaps the idea of a ‘best friend’ is akin to the idea of a ‘soul mate’. As long as you have good people in your life, why worry about having the ‘perfect’ one? I have a few really good friends, I can say that for sure.
I hope that you took something away from this article. I would be interested to hear from anyone else who doesn’t feel like they have a ‘best friend’. I’m interested to hear from people who have grown into and out of many friendships over the course of their life (because that means you’re evolving as a person which is GOOD!).
I’m interested to hear from anyone who has thoughts to share. I shared a lot about my struggles here because I’m sure I’m not alone, but I often feel like I am.
I assume that everyone else does have best friends who they talk to every day. I assume that everyone still has good friends from childhood. I shouldn’t assume these things, but I do. So I have to try and remain focused on what good I have in my life right now.
I actually have one friend right here on medium who is from Chapter Five above!