How to Create Meaningful Connection With Almost Anyone

Use these games to build closeness in as little as four minutes

Devin Gleeson
Jan 22 · 13 min read
Photo by SeventyFour.

At the age of 27, I realized something quite insane: it had been five years since I’d made a new friend.

This realization struck painfully one day as I sat at the kitchen table in my apartment, alone after work.

FIVE years. Could that be true?

It was accompanied by a second blow: Even the friendships I had from previous years were stagnant. They hadn’t deepened or strengthened, and I felt consumed by an increasing sense of loneliness.

At the time, I didn’t know about the growing “epidemic of isolation among young men.” I had no clue about the many significant health costs associated with lack of connection (Stanford Dr. Emma Seppälä’s infographic paints a rather grim picture).

All I knew was this: my heart ached and something needed to change.

That day, I set a strong intention for myself. Whatever it took, I was going to figure out how to create real, quality relationships.

Over the next five years (I’m 32, at the time of this writing), connection — learning how to create it, maintain it, and nurture it — has been the central project of my life. I’ve attended and hosted hundreds of Meetups, lived in and co-created four intentional communities, facilitated groups, coached individuals, and taught workshops — all centered in one way or another on the topic of connection.

The author and his friends. Photo credit: The incomparable Jiawen Liu.

Throughout this work, I’ve observed two really interesting things:

1. We want more connection.

In many cases, people are actually starving for it.

To be clear, that doesn’t necessarily mean we just want to be surrounded by people 24/7. As Dr. Seppälä notes in her TED talk, it’s possible to feel completely alone in the center of a crowd.

What we really want is a subjective feeling of being connected — an internal sense of truly being seen, felt, and known by others, and an internal sense of truly seeing, feeling, and knowing others.

2. We often don’t know how to create connection.

And deep, meaningful connection doesn’t necessarily just happen by proximity. I can (and have) spent days with romantic partners or friends sharing space, time, and experiences, only to feel an acute distance grow between us.

On the other hand, I also know how deeply connecting just five, ten, or fifteen minutes of highly intentional conversation can be.

So, how do we create this type of highly intentional conversation? How do we deliberately concoct spaces where a subjective sense of real connection naturally emerges?

That’s what the rest of this article is about.

I’ve spent years collecting, inventing, and co-creating literally hundreds of games designed to foster deep connection. Below, I’ve curated five of my favorites.

Quick Tip Before We Begin: How to Avoid Awkwardness by Getting “Meta-Awkward”

If you’ve never invited someone to intentionally connect, it might feel awkward and scary to just dive in. That makes a lot of sense. Inviting someone into something like this is the same as saying, “I would like to connect with you more deeply.”

It doesn’t get much more vulnerable than that.

It can help to do something I call getting “meta-awkward.” Essentially, this means calling attention to the awkwardness of what you are proposing when you invite someone to connect.

For example, if I had read this article and wanted to try one of the games, I might say something like:

“Hey, so I just read this article that had a bunch of games on how to build connection and intimacy. It might be a really awkward experience [this is the meta-awkward moment], but I think it’ll be fun, and I’m curious if you’d be game to try one with me?

Getting meta-awkward in this way can have the effect of both defusing the awkwardness while enlisting someone to explore the unknown alongside you. So, be brave. Get meta-awkward. After the first or second time you invite a friend or acquaintance or partner into one of these games, it just gets easier.

Game #1: The Two-Minute Check-In

Time: At least four minutes

Number of people: Two or more

What it’s all about: Whenever I meet with a friend for coffee or sit down with colleagues after the weekend or connect with a project collaborator, I like kicking things off with a Two-Minute Check-In.

Basically, the Two-Minute Check-In is made for just these kinds of connections — relationships where you see people frequently enough that you both generally know what’s going on in one another’s lives as it relates to your relationship, but there isn’t necessarily much awareness around what’s happening for each other in the larger realm of life.

Don’t be fooled by the brevity of this powerful little exercise! You’ll be amazed to discover who around you loves cooking, who’s working on fun side hustles, who’s going through a rough time, who’s plugging away at a first novel, etc.

How it’s done:

  1. Select a person to share first.
  2. Set a timer for two minutes. (You can go up to five minutes with this exercise, but at least do a minimum of two minutes.)
  3. During the two minutes, the person sharing talks uninterrupted about what’s currently happening in their life. This could be about anything — work, love, money, hobbies, passions, you name it. While there’s no specific prompt for this exercise, a good question for loosening the tongue is, “What’s alive in your life right now?”
  4. The other participants simply listen.
  5. When the timer goes off, the sharer wraps up their current thought, and the listener says, “Thank you.”
  6. Then it’s the next person’s turn.

Bonus tip: After trying this practice for a while, you may notice (as I did) that you tend to share in the same way over and over again.

For instance, maybe you only talk about your work when you share, or maybe you tend to focus only on the negative things in life, or maybe you put a positive spin on everything and, as a result, never get very vulnerable.

Whatever your habitual way of sharing may be, try to change things up regularly from time to time.

Game #2: Appreciation Share

Time: No limit

Number of people: Two or more

What it’s all about: I don’t know who to credit for the origin of this particular exercise, but it’s something we started doing in my intentional community as a way to warmly close out our house meetings and balm any discord that may have arisen.

Appreciations are pure magic. They open us up like nothing else. It’s so rare that we turn to the important people in our lives just to tell them how much they mean to us. Likewise, we seldom get the chance to hear how we positively impact the people in our sphere.

How it’s done:

Group version (2+):

  1. Make sure your group is in a circle or square formation so everyone can see everyone else.
  2. Select one person to start.
  3. Have this person make eye contact with the person to their left and deliver an appreciation about them.
  4. After the first person delivers the appreciation, the person receiving simply says, “Thank you.”
  5. Now, the person who just received an appreciation turns to the person on their left and delivers an appreciation to them.
  6. This process repeats until everyone in the group has gone.
  7. When everyone has had a turn, simply pause and encourage the entire group to bask for a moment in the sweet, shared sensation of appreciation.

One-On-One Version:

  1. Select a person to go first.
  2. Set a timer for some agreed-upon amount of time. Between two and five minutes is usually good.
  3. Making eye contact, the person sharing tells the listener all the things they appreciate about them.
  4. When the timer goes off, the sharer wraps up their current thought, and the listener says, “Thank you.”
  5. Then, it’s the next person’s turn.

Bonus tip: Delivering an appreciation is like offering a person a unique gift — a little present that tells them just what they mean to you. After delivering hundreds of appreciations, I’ve found that the ones that land tend to be 1) specific and 2) describe the impact a person has on your life. I’ll give an example.

You could tell someone, “I don’t know what it is, but you’re just amazing, and I really appreciate that.”

Or, you could say something like, “I don’t know what it is, but every time you walk into a room, you bring this quality of nobility and grace that lights everyone up. It amazes me. I’ve noticed it for a long time, and recently I realized how much you’ve inspired me to more deeply inhabit my own nobility and grace wherever I go. So, thank you.”

Which of these do you think a person is more likely to remember?

Game #3: The Five-Five Four-Four

Time: 32 minutes

Number of people: Two

What it’s all about: The Five-Five Four-Four (invented by my dear friend and former partner, Kay) is the most successful tactic I’ve ever encountered for navigating and resolving conflict.

Often when conflict arises, resolution only emerges after three things happen:

  • Both sides express themselves fully,
  • Both sides feel like they’ve been listened to and understood, and
  • Both sides begin to take some responsibility for the argument.

In the absence of a formal structure, however, conflict can easily turn into a festival of argument, interruption, and defensiveness where things escalate and nobody feels heard.

The Five-Five Four-Four gives both people a chance to speak without the risk of interruption not once, not twice, but five different times.

Whenever Kay and I used the Five-Five Four-Four, a sense of mutual understanding and compassion would typically arise by Round Three, roughly 20 minutes into the exercise. Not too shabby, considering some of our disagreements prior to discovering the Five-Five Four-Four could create disconnection that lasted for hours or days.

How it’s done:

Round One: Five-Minute Round

  1. Select a person to share first.
  2. Set a timer for five minutes.
  3. During the five minutes, the person talks uninterrupted about their side of the disagreement. This can include sharing thoughts, feelings, specific positions about the disagreement, etc. “I” statements can be helpful for reducing blame and upping vulnerability (e.g., “I feel hurt when you don’t say goodbye,” instead of, “You hurt me when you don’t say goodbye”), but if this stifles expression too much, scrap it. It’s okay to be messy.
  4. The other person simply listens with as neutral a face as possible. Why neutral? Because even if we don’t make a sound when listening, we can convey our defensiveness or disagreement in our facial expressions. Since this is a space for the speaker to simply share and be heard, it’s better to keep it neutral and wait until our turn when we can fully express our disagreement.
  5. When the timer goes off, the sharer wraps up their current thought, and the listener says, “Thank you.”
  6. Repeat steps two through five for the second speaker, and then move on to Round Two.

Round Two: Four-Minute Round

  1. Round Two is identical to Round One, but you set the timer for four minutes.
  2. When complete, move on to Round Three.

Round Three: Three-Minute Round

  1. Round Three is identical to Round Two, but you set the timer for three minutes.
  2. When complete, move on to Round Four.

Round Four: Two-Minute Round

  1. Round Three is identical to Round Two, but you set the timer for two minutes.
  2. When complete, move on to Round Five.

Round Five: Two-Minute Appreciation Round

  1. In Round Five, you pivot to sharing appreciations.
  2. The sharer begins with the sentence stem, “I appreciate you because…” or something similar, and shares with the other person-specific things that they appreciate about them. Examples might include, “I appreciate you for playing this game with me,” “I appreciate your willingness to always stay connected, even when it’s hard,” “I appreciate how loving you are,” etc.
  3. When the timer goes off, switch directions.
  4. When the final timer goes off, give each other a big hug. You just made it through quite a journey together!

Bonus tip: After you’ve done this practice a few times, you may start to notice that conflicts you have with a certain person tend to repeat themselves. For example, perhaps you feel like your partner doesn’t clean up enough. Your partner, on the other hand, feels like you’re too finicky about cleanliness. This leads to recurring conflicts.

As soon as you notice that you are in a patterned conflict, bring it up at the start of the Five-Five Four-Four by saying something like, “I notice we are having our ‘cleaning argument’ again.”

It’s hard to say exactly why this tactic is so effective, but whenever I have implemented it during a Five-Five Four-Four, it’s had the effect of accelerating resolution and creating a sense of being on the same team — contextualizing a conflict within a larger relational pattern that we are both working on together.

Game #4: Gratitude Exchange

Time: Ten minutes
Number of People: Two

What it’s all about: The scientific literature linking regular expressions of gratitude and overall wellness continues to grow.

While there are lots of solo practices for bringing gratitude into your daily life (gratitude lists, gratitude journals, gratitude meditations), it can be a heart-opening experience to have a practice where you get to both share and hear gratitudes with another person.

That’s what’s going on in the Gratitude Exchange.

How’s it done:

  1. Select a person to go first.
  2. Set a timer for five minutes.
  3. Making eye contact, the first person begins sharing their gratitudes. Gratitudes can be about absolutely anything: joy, abundance, the weather, friendship, sorrow, you name it.
  4. The listener simply listens and does their best to open themselves as a vessel into which the other person pours their gratitude.
  5. When the timer goes off, the sharer wraps up their current thought, and the listener says, “Thank you.”
  6. Then, swap directions.

Bonus tip: There are two basic ways to express gratitude.

The first is to simply use the sentence stem, “I am grateful for…”

In my experience with this exercise, however, it is far more powerful to use the sentence stem, “Thank you for…” as though you are actually thanking the person in front of you for having given you the things you’re expressing gratitude about. This notion might seem strange at first, but give it a try and see if you notice the difference.

Game #5: Internal Reporting

Time: 5–10 minutes
Number of People: Two

What it’s all about: I definitely saved the weirdest for last. Internal Reporting is inspired partially by the world of Authentic Relating, partially by a variety of eye-gazing exercises I learned in neo-tantric communities, and partially by the general curiosity of the intentional community I live in to explore the outer limits of mirror-neuronal empathy and limbic resonance.

There are a few assumptions behind Internal Reporting. The first is that, at any given moment, we are experiencing an endless stream of internal phenomena — sensations, judgments, feelings, thoughts, intuitions, attractions, resentments, etc.

For a variety of reasons, we are highly selective about what we transparently share with those around us. Often when selecting what we share, we tend to leave out the most vulnerable parts of ourselves.

The second assumption is that, when withheld, these vulnerabilities become the greatest obstructions to cultivating deep connection.

Conversely, when shared, these vulnerable parts are one of the single most effective conduits to developing an ecstatic connection with others that there is.

The third and final assumption of Internal Reporting suggests that as we share and hear more of the vulnerable parts, we gradually approach deeper levels of connection that seem psychic. Thoughts, feelings, and intuitions start co-arising such that when we are really connected to someone, we might think of them and suddenly find that they’ve just texted us, or we might tell them that we are feeling sad and don’t know why and they tell us that they are sad because something difficult happened to them that day. It’s magic.

Internal Reporting provides a context for playing with the kind of vulnerable sharing that allows us to open in just this kind of way.

How it’s done:

  1. Sit facing your partner.
  2. Set a timer for 5–10 minutes.
  3. Make eye contact and take three deep breaths together.
  4. Now, continuing to make eye contact, begin to share. Shares should be fairly brief and might include anything from, “I notice that I have a tightness in my stomach when I place my attention on you,” to “I notice that am feeling inexplicably angry,” to “I notice that I keep thinking, ‘this feels really uncomfortable,’” to “I notice that I am feeling attraction toward you at this moment.”
    In this exercise, it’s nobody’s “turn,” per se. Both partners are sharing together simultaneously. A flow might emerge where one person says something, then the next person says something, then the first person says something, and so on. There also might be periods of prolonged silence, or periods when one person shares several observations in a row. Whatever happens naturally is perfect.
  5. When the timer goes off, find a way to close with your partner. This could be through a hug, a nod, a simple “thank you,” or something else altogether.

Bonus tip: The aim of this game is to cultivate transparency and vulnerability. Sometimes, however, it can feel too intense to share the most vulnerable thing. Although there are sometimes benefits to bulldozing straight into the scariest share, another tactic is to do what I call “meta-noticing.”

With meta-noticing, rather than actually sharing the scary thing, you instead share about how you feel about potentially sharing the scary thing.

For instance, rather than telling someone, “I notice that I am feeling attracted to you right now” — an incredibly vulnerable thing to share — you might instead say something like, “I notice that there’s something I want to share, but I feel really scared to say it because I don’t know how it will be received.”

If perfect repression means not sharing anything and perfect expression means sharing with complete vulnerability, meta-noticing allows you to occupy an in-between space from which you can build into progressively more vulnerable things.

Pass It On!

As you test these games in your relationships, I invite you to adapt them, tweak them, and do whatever you need to to make them your own.

Above all, share them — with me, with people in the comments, with your friends and family — and let’s keep the revolution of mind-blowing connection going!

Better Humans

Better Humans is a collection of the world's most…

Thanks to Terrie Schweitzer

Devin Gleeson

Written by

I am a 1:1 life and personal growth coach who cares about people living incredibly rich and vibrant lives. Connect w/ me: https://devingleeson.com/application/

Better Humans

Better Humans is a collection of the world's most trustworthy writing on human potential and self improvement by coaches, academics, and aggressive self-experimenters. Articles are based on deep personal experience, science, and research. No fluff, book reports, or listicles.

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