When You Watch Someone Walk Toward a Pit You Fell Into Once

📍 The Familiar Unease

It’s a strange thing, watching someone else inch toward a place you once stumbled into with your whole heart wide open.

This past week, a younger friend of mine shared that he’d been in a romantic connection with someone for about a month. Lovey-dovey exchanges, budding affection, long conversations, the stuff that starts to feel like possibility. But something about it unsettled me.

The person wasn’t part of our church community, didn’t share his faith, and lived overseas. My friend, being who he is, genuine, kind, and deeply relational, was clearly getting emotionally invested. But I could feel that uneasiness under the surface. So I asked questions. Gently. Thoughtfully. I wasn’t trying to play the role of the older sister who knows everything (because I certainly don’t). I just… recognized the pattern.

Because I’ve been there.

🌀 My Own Detour

Five years ago, I dipped my toes into the wild world of online dating. I was in search of “the one,” armed with filtered selfies and faith-based intentions. However, it felt less like divine appointment and more like looking for a diamond ring at a yard sale.

I swiped through profile after profile—guys with bios that said “just ask,” and conversations that fizzled out before they ever lit up. Some were in it for real connection. Most were just passing time or worse, looking for something shallow dressed up as affection.

I remember feeling spiritually off-center. Like I was trying to force a promise God hadn’t made.

Eventually, I walked away from the apps. A little wiser, a little wearier, and a lot more protective of my peace. “Above all else, guard your heart, for everything you do flows from it” (Proverbs 4:23). And sometimes guarding your heart means gracefully walking away before anything can truly begin.

🧠 A Moment of Courage

So when my friend told me he ended it, just like that. I was stunned. I thought he’d hesitate. But he acted with integrity and clarity, like something in his spirit already knew. I was proud of him. Not because he followed my advice, but because he honored his own conviction.

It reminded me of Solomon, not the wise part, but the part where his love life slowly pulled him from devotion to God. “As Solomon grew old, his wives turned his heart after other gods” (1 Kings 11:4). And if someone as wise as Solomon could be led off course, the rest of us definitely aren’t immune.

A woman once said to me, “Compromise in dating often starts with loneliness, but it doesn’t end there. It ends with spiritual confusion.” I didn’t fully get it at the time. But now I do.

🔍 The Church Dating Dilemma

We don’t talk enough in church about how hard dating can be. Not just practically, but spiritually. It’s not just about who you choose, it’s about who you become in the process of choosing. You start to believe half-love is good enough. That being seen is the same as being known. That spiritual compatibility is optional.

It isn’t.

So no, I didn’t give my friend a sermon. I gave him scriptures. I told him what happened to Solomon. I told him what happened to me. And I prayed that his faith would stay intact and his heart would stay whole. I don’t want him walking around with bruises from a pit I already fell into.

Soul Insights

1. Wisdom doesn’t always come with age—it comes with wounds.

Growth comes not just from time but from trial. The hardest lessons often come with heartache, but they shape our discernment in ways nothing else can.

2. Emotional investment needs spiritual discernment.

Feelings can bloom fast, but discernment roots you deeper. Sometimes what feels like love is just attention dressed up as intimacy.

3. The right decision doesn’t always come with peace right away.

Obedience doesn’t always feel good in the moment. But it makes room for better things to come—real things.

4. Courage isn’t just stepping into something—it’s stepping out.

It takes guts to leave something unfinished, especially when it holds emotional weight. But walking away with wisdom is an act of faith.

5. Guarding your heart doesn’t mean hiding it.

Boundaries protect what’s precious, not what’s broken. You can be open without being reckless. It’s called maturity.

🪞 Final Thoughts: Redemption in the Retelling

When he told me what he did, I nodded and smiled. But inside, I whispered a prayer of thanks. Not just for his decision but for the reminder that God redeems everything. Even the dates that go nowhere. Even the swipes that led to frustration. Even the pits we fell into once.

We don’t always get to stop someone from falling but we can share the story of how we climbed back out.

And sometimes, that’s all the light they need.

Soul Path Insights