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)!

Build community to create memorable experiences

Recently, my partner and I went on our first big long vacation since 2019. We went to Italy for two weeks, which was wonderful. Although we did plenty of things on our own, we did sign up for some tours of historic sites, of museums, of a region’s food. Some of the tours were great and some of the tours were…well, they weren’t horrible or anything. They were simply lacking.

What were they lacking?

My partner and I asked each other this, and we both came up with fairly similar answers. The tours and group activities we enjoyed most were the ones where we had the opportunity to build relationships with the other participants – even if only for a couple hours.

Table with a charcuterie board, a dish of olives, a bowl of bread, and a basket of fava beans. No one is sitting at the table yet,
We did a food tour in Florence, and it was not only enjoyable because of the food (sensory touchpoints), or what we learned, or the tour guide, but also because we got to share the experience of trying new food with other people, and we had the chance to share a table and get to know them and hear about their trips as well.

Of course, leave it to a service designer to want to mull on this a little more…

When designing for someone to have a positive experience, you’re often thinking about what the purpose is, what the desired outcome is, what is the person’s job to be done. A big part of this is meeting expectations and understanding what a positive outcome would be for the customer, event attendee, student, whoever is engaging with your product, service, class, tour, whathaveyou. (I get a bit annoyed at the constant talk of delight in the design process. It makes sense if you’re designing something fun, like game or makeup. When I am renewing my driver’s license, what would delight me is to not have to do it at all!)

In service design, a core question is how to create value for everyone involved—the customer and the business to be sure, but also the employees and others involved in or impacted by the service. While it might be focused on the humans using the service and their experience, it’s not sustainable if it burns out your employees nor if it detracts from the organization’s primary goals. (If a person’s goal is to ensure their kids are safe while they go run errands, perhaps that is not great if your organization is say, a museum, and not a childcare provider or otherwise set up to supervise children. And perhaps not great for the kids either.)

Through the framework of service design, we can break a service down into touchpoints (the things a customer is touching, so to speak, whether it’s packaging or an email), interactions between a customer and employee, and all the other layers of what happens (or is needed, infrastructure-wise) behind the scenes that allow us to deliver that service in that way.

Typically, when we think about what will make something a good experience, we think about touchpoints and interactions. Maybe we want our emails to have a friendly tone, or we want to make sure our staff are trained on how to work with disabled customers and provide various accommodations. Maybe we think about the relationships and try to have an assigned account representative for each client or good practices around entering data into a CRM so that any employee can assist any client smoothly with all of their details and history at their fingertips.

But how often, unless our service is explicitly about creating community, do we think about creating community within group experiences? How often do we consider the interactions between our clients, students, participants?

I’ve been a community manager—where my role was specifically to foster community and knowledge exchange among an evolving group of practitioners. (I still do this for fun in my creative pursuits!) But I’ve also used community building in other roles and in shorter terms.

When I was a technical instructor who was training new staff, I always started each training with an icebreaker. I would ask at least one question that was about us as people outside of work, and I usually tried to ask one question that related to the topic. I did this for a few reasons:

  1. Whatever people were doing before they came to the training, meeting, workshop, or other session you’re facilitating, it’s helpful to give people a way to shift their brains into what you’re about to do next.
  2. Most of the training I led was required onboarding, and it was all on using databases, which is a bit of a dry topic to dive directly into for many people. When it’s a topic that sometimes people dread, or that they’re a little worried will be difficult, it’s helpful to ground people in their existing knowledge. For example, during trainings on using the database to manage event attendees, I would ask people to share about an event they enjoyed and what made it a positive experience.
  3. Everyone in my trainings had recently joined the organization. I wanted to provide a low-stakes opportunity for them to practice introducing themselves with their new role and to get to know other new employees across the organization (a rare opportunity in most large organizations, as this was).
  4. I wanted to model what kind of space this was: a space where they could be seen as more than their job title, where they were invited to participate and use their voice from the start, and a space that, in its playfulness, hopefully felt more like a sandbox and less like a classroom.

Certainly, everyone was there to check the box as something they needed to perform their jobs. But I’d like to believe my efforts also helped reduce any anxiety (a thing in data/technology training) so that they could learn, helped new employees feel a little more seen and connected within such a vast organization, and made it easier for people to reach out to me for help in the future (many did). And that’s valuable to the training participants, it’s valuable to the organization, and it was valuable to me, as an instructional designer – to know what other learning needs there were after the training.

At the time, I didn’t think of it as building community. I thought of it as holding and shaping a space, for that time when we were all together, and creating an atmosphere within that space where we would all be primed for what we were about to do together—so that we may get the most value out of it.

The ability to connect as humans with everyone experiencing the same thing I am in the moment always make things a little brighter, and a little deeper. Growing up in NYC, sometimes we would have blackouts in the summer. And the neighbors emerge from their homes, and we’d sit outside together and talk, creating our own light in the dark.

Build community, even if it’s ephemeral.

It doesn’t matter whether it’s for an hour-long workshop, or a three-hour tour, or if the people will ever see each other again. Sure, having one instructor train 20 new employees is more efficient than training everyone 1:1. But it’s not the only reason to do it.

I’d like to call out that, first of all, it’s far less awkward. Isn’t a little silly to act as if everyone is in their own little bubble and can’t see or hear the other participants? Rather than leaving people to navigate the ambiguous social situation by themselves, we could (as facilitators, hosts, tour guides, et al.) create a starting point for intentional connection.

More importantly, creating opportunities for human creation is another way to add value to the experience. It is human to crave connection. If you’ve ever experienced something and suddenly wished that a specific person was there to share it with you – you know that an experience is different when you’ve shared it with someone. The same way that adding a dash of salt deepens the taste of caramel or that sprinkling in some red pepper flakes near the end of cooking intensifies the other flavors in a dish, that connection makes an experience feel fuller, as if you yourself, in opening up to others, have more fully opened up to that experience.

While you may not build a community that outlasts the event, human connections are the foundation. So why is this post about community rather than about connections? Simply trying to connect people to each other ends up being some sort of transactional speed-dating situation that leaves everyone unsatisfied. But if you think about it in terms of building community, and leave it open to each member to contribute what they will, you create something much better together.