How Do I Make Friends?

When I’ve taught this material, in many different contexts, the most common question asked is, “But how do I make friends? Especially at this stage of my life? 

We’re lonely. Reading a book or listening to a podcast on what makes for a great friendship can be like standing outside a well-lit window of a gourmet restaurant. Hearing how incredible the food is inside only deepens our sense of lack over what we’re missing. 

We could have called this series Recovering the Lost Art of Friendship, for friendship is an art. There are no simple “How to’s” or guaranteed steps to follow. Relationships are messy. People are complex. And like any great art, friendship is easier to talk about and admire than practice. 

And yet there are some tried and true relational skills that, while they don’t come naturally to most of us, can still be learned. There are no guarantees, but if these practices are digested and rehearsed, they can deepen our friendships and make us a little more human. 

  1.     Elevate Investment in Friendship to Urgent Priority 

We’ve seen in this series that the major threat to friendship is not interpersonal conflict, but the inevitable drift away from relationships that are not biological or, strictly speaking, necessary. All it takes for a friendship to fade is… nothing. 

While good intentions and warm feelings might remain – oh, I love being with them! – if you don’t treat making and keeping friends as a life-and-death matter, every bit as important for your future health and wellbeing as your diet and exercise, then you will drift into loneliness. You’ll end up talking about the good friends you used to have instead of talking with your friends when you need them. 

Friendships may begin in serendipity, but great friendships are no accident. 

  1.     Schedule Time or Friends will Slip Away 

My grandfather had a sign on his desk, “We always make time for what’s most important to us.” That’s most always true. The only asterisk I would add is that we are seldom aware of how deeply our unconscious habits, and “the sin that is within” (Rom 7:20) affect our daily choices. And as Annie Dillard famously said, “How we spend our days is, of course, how we spend our lives.” 

There’s an ordinary tragedy in her line, in that we might come to the end of our lives and realize that we didn’t spend our days the way we wished we had, namely, prioritizing relationships with our family and friends. 

An artist writing in defense of making a schedule, Dillard goes on to say, “A schedule defends from chaos and whim. It is a net for catching days. It is a scaffolding on which a worker can stand and labor with both hands at sections of time…it is a peace and a haven set into the wreck of time; it is a lifeboat on which you find yourself, decades later, still living.” 

Habits trump good intentions. If you don’t schedule what you most value, you’ll end up, quite literally without even thinking about it, squandering what’s most important. 

With your closest friends, this looks like scheduling time to speak, preferably face to face, at least once a month. If you don’t schedule it, the tyranny of the urgent will take over. With your very closest friends, it might be an agreement always to take one another’s calls, even if it’s to say, “I’m in a meeting right now. Can I call you right back?” Our friends need to feel that we cherish hearing their voice. Ask your closest friends, “Do you feel like you are a priority to me?” 

For old friends you haven’t seen in a while, this might look like scheduling an annual trip. No one has the time. But at the end of your life, you’re going to remember those experiences above whatever cost of inconvenience kept you from making those plans. Stop putting it off. Catch them while you can. 

  1.     Ask and Keep Asking. Knock and Keep Knocking. 

You’ve heard the adage that the heaviest weight in the gym is the front door. Likewise, when it comes to making friends, the biggest barrier is overcoming the inertia of our comfort zones. To make friends, we must take a risk and reach out. 

Consider too that once you summon your courage, your initial attempt may be rebuffed for any number of reasons. Instead of giving up, thinking, Well, I tried! Expect this journey to be difficult. Why do we think that friendship, any more than love, is something we’ll just “fall” into? Precisely because we are all so pathologically busy, you have to keep initiating, even if it feels one-sided. 

Make it a rule of thumb to knock three times. If that door is not opened, assume the best and move on. Try to remember the person on the other side is just as scared, anxious, and insecure as you are. Who knows what issue or pain is keeping them from opening their door? What’s in your hands is the responsibility to love your neighbor, which will most often feel like getting out of your comfort zone. 

You can even make an investment in easier on-ramps to friendship by buying a Pickleball set, investing in a fire pit, getting a dog, learning the names of the people you routinely see or choosing to be unusually generous – pick up the tab. On your deathbed you won’t regret that you gave too much away. 

  1.     Embrace the Awkwardness 

Awkwardness is the price of admission for beginning a friendship. There’s the awkwardness of that initial invitation, “Want to have coffee or go for a walk sometime?” There’s the awkwardness of talking back to your internal fears that whisper, “I don’t want to inconvenience them” or “they’re too busy.” Let them make that decision, instead of protecting yourself by making it for them. 

Once you dip your toe in, if the friendship is going to grow, there will be new levels of clumsiness as you get to know how peculiar and amazing and crazy each one of you happens to be. 

  1.     Strive to Become a Curious Learner Who Asks a Lot of Questions 

Make the word “curious” one of your favorite words. Strive to be a curious learner and perpetual student, especially of your friends. 

Get curious about the fascinating creature in front of you. They have a heartbreaking story that, as you get to know them better, is guaranteed to make you want to hug them, laugh and cry. When getting to know people, work to replace a critical spirit with a curious one. 

Curious people ask a lot of questions. A mentor of mine often said, “Most people are always willing to talk about their favorite subject – themselves.” The more you are interested in others, the more interesting they find you. To be interesting, be interested. 

Don’t be mechanical about it. Most of us don’t want to feel like we’re being interviewed by an investigative journalist. But because all of us carry a deep desire to be fully known, there’s no end to the questions you can ask when getting to know someone. One of my new friends has a running list of questions he’s catalogued for opening doors. Curate your own list of go-to questions. 

As your friendships grow, study your friends. Get a PhD in Kate or Dave. How do their ancestors show up in their life? What are they passionate about? What would they want to tell their 16-year-old self? Listen for the stories behind the words. Instead of asking “What do you think about that?” Ask, “How did you come to believe that?” 

  1.     Extend the Rare Gift of Listening 

If you’ve ever experienced the privilege of having someone truly listen to you, then you know how extraordinary that is. And you also know that most people go through their whole lives without having anyone ever really listen to them. 

Listening is a form of care. And so much of care is simply slowing down so you can be present to listen. Not to solve. Not to fix. But to hear their heart and validate their feelings. 

When we offer our well-intended advice or share our similar tales of woe, in an attempt to build a bridge of sympathy, it can have the unintended effect of making our new friend feel unheard. If you really want to care for someone, just stop talking and pay attention. Attention is the most basic form of love. Kevin Kelly writes, “Being able to listen well is a superpower. While listening to someone you love, keep asking them ‘Is there more?’ until there is no more.” 

Years ago I burst into tears in the presence of someone who didn’t say a word. After I’d dug up some words and feelings and spilled them out, he just sat there, with me, in that space. He bore that awkward silence. It’s how he was present. I could sense in some deeply intuitive way that he was listening and that I’d been heard. It changed my life. 

  1.     Be Kind and Compassionate, Embody Empathy 

Kindness chooses to see the person in front of you with generous eyes. Especially when they are being prickly like a porcupine, kindness stays present and moves toward with gentleness. Kindness extends a hand when a fist might have been more warranted. 

Compassion is borne of the true humility that the ground is level between us all, no matter what someone might confess or what secret they might disclose. It’s staying aware that given different circumstances you would have done the same or worse, or the deeply felt sense that you already have. Compassion is felt – it reaches out from inside you and is written on your face. 

Empathy is the word in vogue today, though compared to compassion it has limitations that a wise friend will want to remember. But if we use the street-level definition of “walking a mile in another person’s shoes,” then practicing the art of empathy is a key social skill in order to see others deeply. 

David Brooks recently wrote a marvelous book, How to Know a Person, which you could argue is really a book about how to make friends. Brooks writes about how to make great conversation, disagree charitably, counsel a depressed friend wisely, and in general how to come alongside one another. The subtitle reads: The Art of Seeing Others Deeply and Being Deeply Seen. 

As part of practicing empathy and becoming a better listener, Brooks says, “I’ve found it’s best to ask other people three separate times and in three different ways about what they have just said. ‘I want to understand as much as possible. What am I missing here?’” Instead of assuming intent, make Help me understand a familiar question. 

  1.     Be (Appropriately) Vulnerable 

The first ingredient of friendship we looked at in this series was vulnerability. The thing we are most afraid is going to drive the person in front of us away is probably the very thing that will draw them toward you like nothing else. There are no secrets among the closest of friends. You’ll never be free until you are unburdened. As the adage goes, “There’s a secret in his breast; and it will not let him rest.” 

You don’t have to tell everyone everything, and some of the most disclosing people can be some of the least vulnerable. But when you take the risk and dare the uncertainty of emotional exposure, that will draw someone worth the name “friend” toward you faster than any display of strength or story of success ever could. 

One of the secrets of the recovery community is understanding that solidarity around shared weakness in compassionate community binds people together like soul super-glue. My friend calls this, “the fellowship of the withered hand” (Mark 3:5). 

  1.     Learn how to Disagree Charitably and How to Ask for and Extend Forgiveness 

We need a lot of help in learning how to disagree with gentleness and charity. One reason our friendships are so shallow today is that the first sign of real conflict often signals the beginning of the end. We just aren’t equipped, emotionally or spiritually, to know how to enter in and wade through hard, painful conflict. Jesus prepared us for how hard it would be (Matt 5:21-26, 7:1-5, 18:15-35), but we continually overestimate our ability to work through conflict together, especially in the church. 

Exacerbating our struggles, so few of us know how to extend forgiveness. That’s why we need to practice forgiveness in friendships, or we will never have the depth of relationships we want. We need training so we’re not surprised at how hard it is, and we need supernatural grace to give and keep giving it. 

  1. Play the Long Game and Pick Your Battles 

Sometimes people just have what Jeffrey Schwartz calls a “bad brain day.” Friends are people who are learning what it means to bear with one another in love (Col. 3:13). If your friendships are going to endure and deepen, then you are going to have to overlook things that bother you and keep your mouth closed more than you might feel inclined. 

Yes, friends are honest with us. But good friends know that the right thing said at the wrong time or in the wrong way is the wrong thing (Prov 27:14). So, you pick your battles. You don’t have to attend every fight you’re invited to. Overlook offenses knowing you have more than enough of your own. 

One of my “soul friends” once told me that he could see a list of several things I needed to attend to, but that I wasn’t ready or able to hear them all. It was reminiscent of Jesus’ words, “I have much more to say to you, but you are unable at present to bear the burden of it” (John 16:12). 

He practiced incredible restraint – was longsuffering – for months! He listened to what I’d now call my “foolishness,” being ever so careful not to indulge my self-pity by telling me what I wanted to hear. And he made sure to bring every conversation (we talked almost daily) back to the gospel, never in a way that seemed trite or felt dismissive. 

His friendship taught me how to play the long game and communicate care by continuing to show up and be present all along the journey, even when you believe those you care about are persisting in a disastrous choice. 

You might say, “That’s extraordinary to have a friend like that.” You’re right. At certain points in a great friendship each one of you should feel with a shock of gratitude, “I can’t believe that you are friends with me!” 

  1. Speak the Gospel and The Promises of God Over One Another 

If the gospel is ultimately the answer to every problem we are facing, then the gospel is infinitely deep and always applicable. Simple enough that a child can understand it, still we never get beyond, graduate from, or get to the bottom of “the word of the cross.” 

The gospel is more than a statement. The gospel is the unfolding story of what God has done in Christ, is doing now and will do in Christ to reconcile all things in heaven and on earth to Himself (Eph. 1:10). It’s hard to get more comprehensive or cosmic than that! The gospel is a whole new world, a whole new way. 

Because Jesus tells us the truth about reality, friends can help us work through in conversation: what does the gospel mean for this particular problem you are facing? 

At the same time, friends don’t rush us. They make space for the full anatomy of human emotions because God assures us in the Bible’s hymnbook (the Psalms) that we will feel these ways and that sometimes our feelings will collide with what we believe are the promises of God (see Psalm 13, among other lament songs). Friends give us space to complain, to doubt, and to grieve. 

And, at a time and in a way that we may be able to hear it, friends speak the word of Christ over our doubting and frail hearts. 

  1. Be the Kind of Friend You Want to Have 

Some of you might think this list sounds unrealistic. Still, doesn’t this describe the kind of friend you’d love to have? Who wouldn’t want a friend like this? 

Even so, you might object, “I’ve tried my best and been hurt so often that I feel like giving up.” 

It’s been said that behind every cynic is a frustrated idealist. You’ll be a lot happier in your relationships if you lower your expectations. Your friends will be inconsistent and selfish. Instead of being surprised when your friends let you down, expect that even those who care about you the most will sometimes disappoint you (as you will them). “The best of men are men at best.” 

We are never promised friends. But we are called to love one another as Jesus has loved us. If you’re becoming the kind of person we described in this series – honest, loyal and committed; if you strive to love others with even the faintest trace of how Jesus has first loved you; then given enough time, a few people will notice the rare gift you’re offering to them. 

The ancients had a saying that the reward of virtue is virtue. Friendship is the same. The reward of friendship is friendship. Friendship doubles our joys and halves our sorrows. A gesture of friendship is never in vain and will not return void. In the (very) long run, the way of the cross always leads to life. 

Conclusion: Simon of Cyrene as an Icon of Christian Friendship 

There’s a scene in the gospels where a man named Simon is asked to carry the cross of Jesus as our Lord made his way to Golgotha. 

You might think that’s a strange picture to close our series on friendship, especially as we are told that Simon was a “passerby” who had been “compelled” to assist. 

And yet, we have reason to assume that Simon became a follower of Jesus as his sons, Rufus and Alexander, were evidently known by the community to whom Mark was writing (Mark 15:21). 

This image of burden-bearing in a cruciform manner (and cruciform means cross-shaped) captures the daily shape that Christian friendships should take. We “bear one another’s burdens” (Gal. 6:2). 

Simon was compelled to do this for a stranger who became his Lord. Every day, as we have opportunity, we can rehearse this scene, and in so doing turn strangers into friends, for who wouldn’t want to become friends with someone who sacrificially helps you? Coming alongside to carry things too heavy for one to carry alone is precisely how close companions become the dearest friends. 

Cruciform friendships – completely unexpected but radically generous – make for the deepest and most satisfying relationships. And we have a chance to practice burden-bearing as long as the people walking alongside us have burdens, which is to say, every day is a fresh opportunity to become a friend.