What I learned from 50 (mostly) first dates

It’s odd getting to know people as an adult, isn’t it? As a kid, it’s often by proximity – we make friends with the neighbors, kids in our class, or kids who take the same route home after school. As we get older, it’s often through school, perhaps a place of worship or an extracurricular activity, and then at work, or maybe kids’ schools/activities in the case of people who are parents. But what about outside of institutions?

A latte with latte art in the foam on the top to look like two hearts, with a spoon on the saucer, and a tall mug of black coffee to the right. Both cups are on a wooden tray on a wooden table.

Last month, I watched a friend’s six-year-old run around making friends with random children, all readily jumping in to play with each other even though none of the parents knew each other nor necessarily interacted with each other. Nobody had set up a play date. I envied his ease – their ease, I should say, since while he wasn’t shy to jump in, every kid he interacted with was eager to welcome another person to play with. They were simply happy to be playing.

I envied their seeming ease – but actually, in terms of what I saw happen, I’ve found that this generally resonates with what I’ve found as an adult attempting to meet new people.

Earlier this year, I set a goal for myself of having coffee (or lunch or a virtual chat, etc.) with 50 different people. Having moved to a new city (and country) in 2022, I figured that it would be good to get to know people, whether personally or professionally. This was not for romantic purposes (I’m fortunate to have already found a wonderful partner!), nor did I have any specific agenda beyond getting to know people.

As someone craving connection (a.k.a., a human), I also counted people that I already knew, though I tried to make a point to reach out to people I crossed paths with once and wanted to get to know better. So I counted every substantial conversation for the first time I met with that person in 2023, and I counted them whether we met for coffee, shared lunch or a beverage, had an extended conversation during an event, went for a walk in the park, had a virtual meeting. I counted any conversation where I felt like I came away knowing something about the person that I didn’t know before. They included people I met while in the US and while in Japan, and some I’ve only met virtually, but have included people from numerous countries.

Of the 50 conversations, 32 were with people that were new (new as in, we’d never really had a substantial conversation or talked 1:1 before). I’m proud of that. It’s easy to talk to someone for a few minutes at a networking event, connect on LinkedIn, and then never go beyond that. But what’s the point if you’re not even sure why you might want to stay in touch with them besides that they work in the same field? (On top of that, field being fields for me, and even then, pretty loosely defined in my case.) However, I’m also grateful to everyone who made the time and for the things I learned from each of them and along the way.

What did I learn?

  • People are generally pleasantly surprised when you have a great conversation at an event, exchange contact information or connect on LinkedIn, and then actually follow up to schedule a coffee or virtual chat.
  • It works best to reach out for a chat when based on a real connection, when it’s clear that this is not transactional (i.e., not trying to sell something nor use Meetup or LinkedIn as a dating service), and when you reach out within the next few days after meeting them.
  • In a couple cases, I met people through a mutual acquaintance and this can be another strategy for meeting new people. For example, if you’re interested in meeting people who live in a particular area or who say, share a hobby, ask your existing networks!
  • I felt most awkward reaching out to people whom I’ve known casually (in that we crossed paths once or have a mutual acquaintance, etc.) for some time but whom I don’t actually know well. But most of the time, the other person expressed that they had wanted to get to know me better, too, and they were glad I had reached out.
  • Like exercise, reaching out gets easier over time and with practice and remembering that the point is to get to know people – not to have every person you meet like you.
  • There were people I never heard back from. Maybe they didn’t remember meeting me, or maybe it got lost in a cluttered inbox, or who knows what else is going on in their lives – I didn’t take it personally. If I eventually hear back, I look forward to talking with them!
  • You won’t become long-lasting friends or end up working with or hanging out with everyone, and that’s okay. But even if we haven’t really talked much after that initial chat, I’ve still always learned something. I know more about that person and the things that they’re interested in, and hopefully they know something of me—both of which are always wins in my book. The conversations are interesting and sometimes I get to learn other things as well, such as about a field unfamiliar to me, or practical tips for life in Tokyo. (The latter has been especially useful the past year!)
  • Over time, I’ve gotten better at recognizing a genuine connection in the moment (it often involves a lot of laughter in my case) and where we might both enjoy having a more in-depth or 1:1 conversation.
  • There are few things that bond people as quickly as a common and emotionally intense experience. You know, like moving to a country where you don’t really know anyone and can’t really speak/read the language.
  • We are each of us so much more than a job title, or a family role, or our passports, or the things that happened to us. It’s a reminder I’ve really needed for myself this past year.

Someone I once worked with on a project shared with me that, when he worked in sales, he was trained on always having a brochure or something to physically hand a potential customer so that they would have to extend and open their hand to receive it. In doing so, the potential customer would be opening up their body language and, so the theory went, their mind would follow.

I’m not sure if that’s true, but it is human to want to connect with people. Often, people are interested in connecting or talking further, but they may be nervous about reaching out or simply haven’t had the time to follow-up. But that’s not the same as not being open to it.

If you’d like to get to know more people or get to know people better, reach out first. People are more open than you think. There are many kind, gracious, and generous people in the world. Be kind. Be curious. Be real and people will be real with you.

Thoughts? Done something similar? Have other recommendations for meeting people or getting to know people better? I’m open to hearing from you (and to having a chat)!