Hope That Disappoints
The Ache of Unmet Hope
It’s no secret that dating in your 30s can feel like the Wild West. If that’s news to you because you’re happily married, I hope you’ll keep reading—not to feel guilty, but to better understand your single friends. I truly celebrate the gift God has given you. But this Advent season, one of the greatest gifts you could give is empathy: walking a mile in your single friends’ shoes.
As I write this, I’m 37 years old and single—never married. Forty is approaching quickly, and this is not the story I imagined for myself. I know many others share similar stories, even if the details differ. The common thread is the same quiet question: How is this my life? It’s not that our lives aren’t good or that we aren’t grateful for God’s blessings. It’s simply not what we expected. And whether you’re single or not, we’ve all experienced the ache of reality falling short of our hopes—of placing our hope in something that ultimately disappoints.
When Dating Doesn’t Go as Planned
This holiday season, I hoped things might be different. I hoped to go on a few dates, maybe meet someone who would make the season feel less lonely. It had been a while since I allowed myself to hope like that, so I already knew I was taking a risk. I stumbled upon a texting speed-dating event through an online dating app (and yes—speed dating via texting is a recipe for carpal tunnel). After years away from online dating, I decided to give it a chance, overanalyzing my profile far more than I’d like to admit. First impressions matter, right?
When the event started, with sweaty palms and a racing heart, I chatted with men from all over the country. The conversations were…memorable. One guy was recovering from a heart attack in the hospital (why are you speed dating right now?), and another said he hoped I could cook because his specialty was cereal (yikes). But by the end of the night, one guy stood out—and he lived just two hours away. I thought, This might actually be promising.
When Hope Feels Risky
Over the next week and a half, we texted regularly and began getting to know each other. Dating experts say it’s best to move past texting quickly, since it can be misleading, so we made plans to meet in person. Our conversations ranged from lighthearted to deeply personal as we shared our stories, our pasts, and who we are now. It felt honest. It felt like progress—until suddenly, it wasn’t…
Three days before we were supposed to meet, he slammed on the brakes. We hadn’t texted that day, which I assumed meant he was busy. Then came the first message: he wasn’t ready to date and didn’t want to waste my time. I was blindsided. Everything had seemed to be moving forward. While I knew he had experienced past hurt, he had appeared ready and excited. I asked a few clarifying questions—and then it was over.
Hope Shattered.
At first, I was in shock. But as the days passed, sadness settled in—not just over what could have been, but over old emotions I had never fully dealt with. You might be thinking, How could you feel this deeply after talking to someone for a week and a half? And you’d be right—it sounds small. But when you’ve allowed yourself to hope again and again, only to be disappointed again and again, the weight compounds. It goes from zero to one hundred in an instant. Shame creeps in, whispering, I can’t believe you opened yourself up to this again. It feels safer to shut hope down entirely. And yet, something always nudges you to try again. When it falls apart, anger and sadness rush in—and shame amplifies them all. I can’t believe I placed my hope in something that disappoints…again.
Advent, Waiting, and a Hope That Endures
If you’re still reading, you may be wondering what any of this has to do with Advent. Stay with me—this is where it all came together. Advent is a season of waiting with hope. The Israelites spent hundreds of years waiting for the Messiah. Along the way, leaders arose who seemed promising, only to fail or die. Again and again, hope rose—and again and again, it was crushed. Weariness set in. Frustration followed.
It wasn’t that God failed them. He was in control all along, perfectly aware of the right moment for Jesus to arrive. But the people kept placing their hope in someone who would ultimately disappoint them. And honestly? I can’t fault them. Waiting is hard. So hard. My dating story simply helps me identify with their longing.
Let me be clear: waiting for a spouse and waiting for the Savior of the world are not the same. My experience pales in comparison. But the pattern is familiar. We all place our hope in people, circumstances, or outcomes that fall short. We all experience that mix of anger, sadness, and shame. And that shared human experience connects us to the Israelites—and to Advent today. There is only one hope that does not disappoint: Jesus Christ.
Romans 5:3–5 reminds us of this truth:
“And not only that, but we also boast in our afflictions, because we know that affliction produces endurance, endurance produces proven character, and proven character produces hope. This hope will not disappoint us, because God’s love has been poured out in our hearts through the Holy Spirit who was given to us” (CSB).
Paul wrote this to Christians facing severe persecution, reminding them—after Jesus had already come—that their hope would not disappoint them, even when life was painful and unexpected. And while my story is far less severe, it reminds me of the same truth: even when life doesn’t look the way I imagined, God is still good, still present, and still offering me a beautiful inheritance through Jesus. And He offers the same to you.
Holding Hope in the Waiting
This was hard to write. I strive to model a strong, content, single woman—and that can be true while also acknowledging unmet longings. Strength doesn’t mean the absence of struggle. So to anyone wrestling with singleness, or any unfulfilled hope this Advent season, I pray my story encourages you to place your hope in Jesus—the only hope that will never disappoint.