How to Have Deep and Meaningful Relationships When You Can't See Anyone In-Person

At the beginning of 2020, I had exciting new goals to go on more dates, learn how to dance bachata, and take an improv class. My job at Catalyst Community (now MMT) gave me the opportunity to host events for local entrepreneurs that ranged anywhere from small, intimate dinners to day-long gatherings like Celebrate Toronto 2020.

But once COVID hit, our team had to cancel all the events that we had planned for the year... which ultimately shut down our new business. Plus all of my personal goals that involved, you know, meeting other people... was no longer an option.

As a single man living alone in a small apartment, 3,000 miles away from family, I had a feeling that this was going to be a looooong couple of weeks year (and counting).

I knew how important human connection was to me and immediately became proactive around creating space to connect with my community.

By the end of the year, I surprisingly felt connected with my friends and even closer to my family.

I know we can't see people like we normally could. But I do believe that the 2nd best option, remote socials combined with some intention-setting, can actually help much more than you think.

I'm sharing everything that I did to help me maintain meaningful relationships with my loved ones. My hope is that this essay can help you (or someone you know) feel more connected with your friends and family. Enjoy!

Start or join a social group

At the end of March, I started a small workout group over Zoom with friends and friends of friends to get six-pack abs not get fatter than I already was.

I'm usually the last person my friends would think to start a workout group but I knew I needed it for my physical health and honestly, I simply used this as an excuse to connect with old and new friends!

We'd all get together on Zoom and do a 30-45 minute workout video on YouTube (We like HIIT, Abs, Calisthenics). While it's great that we worked out together, I definitely wanted some time for conversation, so I added an activity called "Stretch and Share" after our workouts.

Anybody could propose a prompt to the group like:

  • "What are you looking forward to in the next 30 days?"
  • "What have you been doing lately for self-care?"
  • "What's been on your mind?"

Then each person would name a stretch they want to do like stretching our triceps. While we are all stretching in that position, that person would share their answer to the prompt. Then we would pass it on to the next person to lead a stretch and share their answer.

We're so wholesome eh? 😉

I reconnect with old friends. I connect with my best friends. Plus, I have met new friends who I had never met in person yet, and feel oddly close to them because of this opportunity to connect consistently.

We've been going strong since March 2020 and been staying physically active because of this group!

I also started a weekly poker group that lasted for a few months that was a TON of fun. We'd get on Zoom every Weds night and play poker against each other. As the organizer, I also got invited to join other poker games, which gave me more opportunities for connection.

My friend Sol Orwell highly recommend cooperative games like Among Us and Codenames. He and his friends get together for fun games for most weekends and even added a food-delivery swap element which is so cool!

The best thing about hosting these groups is that you don't necessarily have to know people to create a community.

I've never met half of the people in my workout and poker group before I hosted the event. They were mostly friends of friends first, but are now my friends since we've gotten closer.

If working out, poker, or board games are not your thing... find something that you're curious about: learning a new language, an interesting book, or meditation.

Then find just 1 buddy to meet with on a consistent basis to connect and eventually, you both will invite 1 more person, and they will invite more people... so you have this organic group of folks who you get excited to see every month!

Start or join a mastermind group

One of the biggest parts of my day job at MMT is to facilitate mastermind groups for entrepreneurs. We meet once a month, every month, for a year with the same group of members. The purpose is to have a safe space to overcome obstacles and maximize opportunities that come your way with a trusted peer group who are on your side.

I've facilitated every session for four groups since the start of COVID and have seen members at their lowest lows and highest highs.  What they tell me behind the scenes is how valuable it is to have a safe space like this to get them through, and ultimately thrive, during the hardships that most small business owners had to endure.

Taking that same idea, I created a Relationship Mastermind Group, to help me with my personal goal of getting into a long-term relationship!

The title sounds fancy but it's nothing special.

Our mastermind is just six friends who meet once a month to talk about relationships. But more importantly, it's a safe space to share openly about your challenges in your relationship and for the group to support you.

It's been amazing to have open conversations with friends I love and respect with sensitive topics that we don't usually bring up in casual conversations. We touch on topics like:

  • How should I resolve this conflict with my partner?
  • What are your non-negotiables in your ideal relationship?
  • Where does emotional labor play a part in your relationship?

While none of us are relationship experts, we share our own experiences, advice, and resources that may be helpful. We listen to one another. We celebrate our wins. We support each other during times of hardship.

Plus, it's another excuse to see your friends!! (Are you getting the point yet?)

You don't need to start a "mastermind" per se but having a safe space where you can be vulnerable and 100% yourself are some of the keys to building close friendships.

Have consistent 1 on 1s

While I love doing things in groups, nothing beats a 1 on 1 conversation with someone you love.

I used to call my mom once a week or every other week while I lived in Toronto and she lived in Los Angeles. We caught up for 15-30 minutes or so with just casual conversation. It was nothing that special.

But once COVID hit, I saw it as an opportunity to see my mom more often. So we agreed to a Zoom catch up every Sunday at the same time each week. We talked for 30 minutes or so and afterward, we would do yoga together, as a way to move our physical body and calm our minds.

This new ritual was one of the best things that came out of COVID for me. While I could have arguably done this at any time, this time of isolation was the catalyst for me to invest more time in something I should have done a long time ago.

Outside of Zoom hangouts with my mom, I totally acknowledge that Zoom fatigue is a REAL THING. Being on my screens all day with work and then catching up with friends through a video call is exhausting.

So when I catch up with friends now (usually 1-2 calls a week), I always suggest talking on the phone, for a walking meeting! It's nice to get outside and moving after we have both been inside all day. Walking puts me in a better mood and helps me be more present.

In whatever way you do these 1 on 1s, try to make them consistent. It could be once a week, once a month, once a quarter. Whatever cadence you want.

Repeated interactions will significantly deepen your relationships.

Show up for your friends when they need you most

Over the past year, I've had different friends get divorced, relapse, and lose loved ones. I've had family members break down and cry because of mental health issues. I've witnessed "successful" entrepreneurs get their whole businesses wiped out and suffer in silence.

What is happening around the world is terrible and heartbreaking - there's no getting around that. This is why it is even more crucial to show up for the people in your life that need you the most.

It's easy to avoid talking to someone who is suffering because you may not know what to do or say. I've been in that situation PLENTY of times.

Life can be more simple when you look the other way and go about your life.

But if you ask anyone who is suffering, most of them are silently crying for help, and often feel like they don't want to be a burden on others.

It's better to do something than nothing.

If you have the capacity in your life to support others, reach out to those who are suffering. It doesn't have to be extravagant. Simply a text or email asking "How are you?" is more than enough to start.

What you say doesn't matter as much as them seeing you putting an effort to care for them.

Final Thoughts

When I die, I am not going to reminisce on all the work that I've done or how many Twitter followers I had. I'm going to think about what mattered most: friends, family, and all the shared experiences we had together.

If you value having strong relationships but haven't taken action to engage deeply with your friends and family, now is the time to do so.

Sending you a big virtual hug to wherever you are in the world!


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