Gen Y Speaks: Making and keeping friends as an adult is tougher than I thought. Here’s what helped

We met at a book launch event. Over dinner, we had a funny conversation about how cool Swedish people were. We joked about how we too wished we could start something like Spotify, or even Ikea. 
I asked her if we could keep in contact. She hesitated. 
“I have a boyfriend.” 
Seriously? That escalated quickly; the mere suggestion of keeping in touch had somehow leapt into being interpreted as a romantic invitation. 
I confess: I, a born and raised Singaporean, don’t quite understand how to make and keep friends in Singapore. 
In my 20s, of all the problems I would face, I’d never expected loneliness to be one of the biggest ones. Of all the subjects we’d learnt in school, at least one should have explained how hard making and maintaining friendships would be in adulthood. 
I’d always dismissed it as a problem for older people. After all, a lifetime of sitcoms had taught us that being in your 20s is all about being mobile, sociable, and entirely able to make friends. 
But week after week, I found myself staring down the barrel of an empty Sunday afternoon and wondering how I got there. 
Don’t get me wrong — I’m not uncomfortable being alone. I make it a point to date myself once a week, taking time to watch a movie alone or have a good meal on my own. 
But at some point, I realised a need to feel emotionally connected with others. As former US Surgeon General Vivek Murthy wrote in his book Together, loneliness is “the absence of physical and emotional connection”. 
I longed for and craved that emotional connection. 
In their adulthood, people commonly return to the friendships formed when they were younger, such as secondary school or university friends. 
In most of these friend groups, I took on the role of initiator by default. But slowly, I got tired of coordinating times, and of figuring out where to go and what to do.
“Sorry, I’m busy” became one of my most hated phrases, especially when there were no attempts to suggest alternative timings. I was putting in the effort, but I wasn’t seeing the same from my friends. It felt like I was being taken for granted.
Some others would not commit until extremely late, perhaps three days before the meeting date. People who often do this can make you feel as if you are simply one social option out of many, and they are more concerned with gauging which one would be the most beneficial to them. 
I don’t blame them. For most working young adults, our jobs already take up so much time and energy — of course one would want to make the most of any free time, with the right people. 
So I went on a mission to make new friends. 
It started with attending social events like book clubs and mixers. Whenever I had a decent conversation with a new acquaintance, I would ask if I could keep in touch. 
Most of them were willing to keep in touch via Telegram handles. But then any text conversation would usually die, as there was no real reason to continue chatting outside of the event we had met at. Some would also ‘ghost’ me or not reply altogether. 
None of them explicitly told me this — but I have a sneaking suspicion they’d assumed I was trying to either sell them something or date them. 
Singaporeans are a pragmatic people, much to both our benefit and our detriment. Here, new connections are often approached in a transactional manner. The receiving party’s default frame of mind seems to be: “What does this person want from me?” 
For us, connections often aren’t relational — rarely are they the point in itself. 
Conversations become about networking, instead of just sharing a good laugh, a funny story, and good company. 
Whenever we’re approached by a stranger, it’s hard for us to imagine that they have no agenda beyond just friendship. 
Is making and keeping friends simply impossible in Singapore? 
May, 2022: While passing through my neighbourhood, I heard shouts and the familiar thwack of a ball against a wall. I followed the sounds to the soccer court, where a handful of youths were playing. 
Embarrassed, I asked if I could join them. It was awkward, and I was aware: Here I was, a 26-year-old man, attempting to join a group of 13- to 16-year-olds. 
Much to my relief, these boys kindly and gladly welcomed me. 
Over the past 18 months, we’ve become more than just players sharing a court. They share their troubles in school with me. I share my troubles about work and dating with them. 
Just like that, in the most unexpected of places, I found — dare I say it — friends. 
What makes upkeep of this connection easy is that there are no elaborate efforts to try and find common timeslots. You just appear, and play. 
Now, when I meet someone new and ask to exchange contact info, I quickly add: “I’m not trying to date you.” 
This clarity appears to help. (I’ve not been rejected yet, at least.) 
But perhaps the most important of my takeaways is to be intentional with friends, both old and new. 
To keep in touch with people, we first need to know who we want to keep in touch with. 
One exercise I found helpful was the making of a friendship map — something I lifted from We Need To Hang Out by Billy Baker. 
For this, Baker uses Dunbar’s Number — anthropologist Robin Dunbar’s theory that 150 is the typical number of people we can keep track of and consider part of our ongoing social network at any one time.
What’s more interesting are the numbers in between: Dunbar estimates that we would have about five close friends, 15 we would consider family, 50 we would see as part of our clan, and the remaining 80 as part of our tribe. 
Baker also relies on the internal question: “Would you want to ask this person out for coffee if you randomly bumped into them?” If the answer is no, or “it’d be awkward”, it’s likely that they aren’t someone you would consider a friend. 
I like to think friendships are like clothes. 
Different clothes are good for different seasons. You can’t change the season to fit the clothes you wear. Instead, it’s more ideal that you wear clothes that fit the season. 
There are the tough seasons, where all you want each weekend is friends to have fun with so you can forget about work or whatever struggles you’re facing during the week. 
Then there are the seasons where you have a little more time. During these periods, actively nurturing my friendships, rather than leaving them to chance, reminds me of what makes life meaningful. 
But, regardless of weather, clothes can and will spoil. When that happens, you need to decide whether those friendships are still fit for purpose. 
Often, though, such friendships can be worth a mend. Try something new with your friend — play a sport unfamiliar to you both, explore a new country, or embark on a new adventure together. 
The important thing is to do something. Take action. Chances are, if you are thinking of a friend, they’re probably also thinking of you. 
It’s not just because your friends are worth it. 
It’s because you, too, are worth hanging out with.
ABOUT THE AUTHOR:
John Lim speaks on creating happier workplaces for millennials and is the author of the book Take Heart: Thriving in the Emotional Wilderness. He blogs at www.liveyoungandwell.com/blog.