Best Friends, Boundaries, and Breakups

This is the last post in our short relationships series. We’ve talked about why we’re lonely in the first place and what dating is actually for. Today we’re talking about best friends, boundaries, and breakups — three things almost everyone is navigating right now, whether they’d use those exact words or not.

Not Everyone Is Your Best Friend

One of my pet peeves — and I know it’s a small thing to get worked up about — is when people call everyone in their life their “best friend.” You’ve seen it: someone’s birthday rolls around and suddenly they’ve got twenty best friends. But not every friend is a best friend, and calling them all that actually devalues the handful of people who really are.

There are friends, and then there are best friends. Friends come and go. Best friends are the ones who stick around for years, not months, and who you’re an open book with. So how do you actually become someone’s best friend — and more importantly, how do you stay one?

Here’s one test worth applying, to others and to yourself: do their friendships last for decades, or do they tend to discard people after a few years? If you’re dating someone, or thinking about marrying them, look closely at their friendship history — and look just as closely at your own. How long have your friendships lasted? How have they ended? Is there a pattern? These aren’t comfortable questions, but they’re worth asking before you’re standing at the altar rather than after.

What Jesus’s Friendships Teach Us

The Bible is full of friendship, and one of my favorite examples is Jesus and his inner circle — Peter, James, and John. These guys would’ve been a fun hang. They were also present for some of the most significant, shaping moments of Jesus’s life, and a few of those moments teach us something real about what it means to be a good friend.

Serve Your Friends

Now about eight days after these sayings he took with him Peter and John and James and went up on the mountain to pray. And as he was praying, the appearance of his face was altered, and his clothing became dazzling white. And behold, two men were talking with him, Moses and Elijah… Now Peter and those who were with him were heavy with sleep, but when they became fully awake they saw his glory and the two men who stood with him. And as the men were parting from him, Peter said to Jesus, “Master, it is good that we are here. Let us make three tents, one for you and one for Moses and one for Elijah” — not knowing what he said.

Luke 9:28–33

Peter’s response is a little awkward — he doesn’t even know what he’s saying — but it’s also completely in character. He’s watching his friend at the most glorious moment of his life, and his instinct is to serve, to build something, to do something useful for Jesus in that moment. That’s a good instinct to borrow. Good friendship looks for ways to serve, even when you’re not totally sure what that should look like yet.

Loyalty That Tells the Truth

When the days drew near for him to be taken up, he set his face to go to Jerusalem. And he sent messengers ahead of him, who went and entered a village of the Samaritans, to make preparations for him. But the people did not receive him, because his face was set toward Jerusalem. And when his disciples James and John saw it, they said, “Lord, do you want us to tell fire to come down from heaven and consume them?” But he turned and rebuked them.

Luke 9:51–56

James and John wanted to torch a village on Jesus’s behalf, and Jesus shuts it down. That’s a good picture of real friendship — it isn’t blind loyalty that fuels your friend’s worst instincts. It’s telling the truth even when your friend wants backup for something they shouldn’t do. A good best friend is willing to be the one who says no.

Be There in the Hard Times

Then Jesus went with them to a place called Gethsemane, and he said to his disciples, “Sit here, while I go over there and pray.” And taking with him Peter and the two sons of Zebedee, he began to be sorrowful and troubled. Then he said to them, “My soul is very sorrowful, even to death; remain here, and watch with me.”

Matthew 26:36–38

In his most sorrowful hour, Jesus asks his closest friends for one thing: stay awake with me. They fall asleep instead — more than once — but the ask itself tells us something. Real friendship doesn’t disappear when things get hard. It shows up, even if it doesn’t know what to say or do, and just stays in the room.

Boundaries: A Fire in Its Proper Place

Every relationship needs boundaries — with your parents, your friends, and especially in dating. We tend to let people in fully the moment we start growing close to them, without asking whether that’s wise yet. Some of you know exactly what I mean when I bring up soul ties; others have never heard the term. Either way, the picture I keep coming back to is fire: a fire in a fireplace is warm and beautiful. That same fire loose on the living room floor is a disaster. It’s not that fire is bad — it’s that fire needs a proper place to do what it’s good for. Relationships work the same way. Without boundaries, things that could be beautiful end up burning the house down instead.

Getting Through a Breakup

Even when you do the first two things well — investing in real friendship, holding healthy boundaries — you can still end up walking through a breakup. Two emotions tend to show up together: rejection and confusion. You don’t have to carry either one alone.

For we do not have a high priest who is unable to sympathize with our weaknesses, but one who in every respect has been tempted as we are, yet without sin.

Hebrews 4:15

Jesus knows rejection firsthand — he was rejected by his own hometown, by religious leaders, eventually by the crowds who’d cheered him days before. Whatever rejection you’re carrying, he’s not distant from it. And the confusion that comes with a breakup, the endless replaying of what happened and why, is normal too. It doesn’t mean something is wrong with you; it means you’re human.

How to Do It Well: Honesty and Humility

If you’re the one ending things, honesty means actually telling the truth about why, instead of fading out or leaving someone guessing. If you’re the one being broken up with, humility means resisting the urge to relitigate every detail or demand the other person justify themselves further than they already have. Neither of those is easy. Both of them are what it looks like to end something well instead of just ending it.

Where the Series Leaves Us

We started this series with a simple observation: most of us are lonelier than we let on, even surrounded by people. From there we talked about what dating is actually for, and now, what it looks like to build friendships that last, hold healthy boundaries, and walk through breakups with honesty instead of running from them.

None of this is really about technique. It’s about becoming the kind of person who loves God and loves people well — in whatever season of relationship you’re actually in right now.