What follows is a true story. I'm telling it now, two years later, because someone needs to read what the beginning looks like — before they recognize their own.
Online dating is a nightmare. I hate everything about it. But what else am I supposed to do? It's not like some cute guy is going to magically hit on me while I'm squeezing avocados at New Seasons. Maybe this time will be different.
I was in the middle of one of my usual lazy evenings — lying on the couch, half-watching TV — when my sister messaged me out of the blue about a dating app she'd just heard of. A Christian one called Upward. She knows I've been on my journey with Christianity, so I thought it was nice of her to mention it.
I wasn't holding out for a miracle. I've seen enough of these apps to know they're basically all the same: vague profiles, conversations that fizzle out, and ghosting galore. But I was curious enough to humor her. Maybe it would be different. So I downloaded it, trying not to roll my eyes the entire time.
The first thing I noticed was that the app wasn't exactly user-friendly. The UI was clunky, and navigating through profiles felt like operating a machine from the early 2000s. I already hated it. But I dutifully filled out my profile — because what else was I going to do? I wasn't expecting much. After my experience with Hinge, my optimism was more than a little bruised.
Still, as I started swiping, I noticed something. There weren't as many fake-looking profiles. You know the ones — every guy looks like he walked straight off a movie set, job title suspiciously perfect, surgeon who surfs in his spare time and rescues puppies. I've had enough of that. But here, the profiles looked real. I even came across a few people who went to my church. That intrigued me enough to keep swiping.
Then I saw him.
He wasn't the kind of guy who would normally stop me in my tracks. But there was something about him. Big blue eyes, clean-cut, with a slightly dorky smile that somehow made him even more charming. His photo was terrible — just one picture, poorly cropped, like someone's mom had snapped it and accidentally chopped off half the background. But it didn't scream fake. It felt real. He felt real.
His profile was simple, almost too simple, but there was something genuine about it. Nothing flashy. No attempt to sound too smooth or too perfect. He had a quote: As iron sharpens iron, so one person sharpens another. Weirdly enough, my pastor had just been talking about that concept on Sunday. I appreciated it. His name caught my attention too — unique, just like mine, and starting with the same letter. Totally superficial. I noticed it anyway.
Still, I hesitated. He was six years younger than me. I've never dated anyone younger, and that threw me off. I wondered if it would be weird — if he'd be immature, not at the same stage of life. But I reminded myself I was just swiping on a photo. It wasn't a commitment. So I thought, what the hell. What's the harm?
Well he messaged me some time later and I made a joke about him being a catfish for only having one picture, and to my surprise, he immediately sent another. A bathroom selfie — though it looked more like a gym locker room. What struck me wasn't the setting. It was how different he looked.
More muscular than I'd imagined, with a high skin fade — something I personally thought looked terrible. But he didn't look young or baby-faced the way I'd feared. He looked his age, with a seriousness in his expression I hadn't seen in the profile photo. I messaged back: "Why do you look so mad?" He didn't seem offended. I took that as a good sign.
I wish I'd saved our initial messages. Like anyone who enters a relationship in the digital age, I deleted the app two weeks in. It didn't even occur to me to keep the conversation.
What I do remember is that from the start, it was easy. Effortless, even. I'm used to the usual small talk — Hi, how are you? What do you do? Repetitive, boring, leading nowhere. But with him, the conversation just flowed. We joked from the beginning and it wasn't forced. No awkward silences. No dead-end questions.
We started with the usual pleasantries, but there was a spark there. Something clicked. Over the next week we talked about everything: politics, religion, our experiences on the app, favorite foods. The typical stuff you go through when you're feeling someone out, deciding if they're worth meeting in person.
What struck me most was how aligned our worldviews were. After a few bad dating experiences, I'd realized how much easier things are when you see eye to eye on the big stuff.
But it wasn't just that. He wasn't in a rush. Unlike so many guys I'd talked to, he didn't immediately comment on my looks or steer the conversation somewhere sexual. Didn't ask for my number after three messages or push to meet up right away. That's one of my biggest pet peeves — guys so eager to meet that they can't be bothered to get to know you first. He didn't do any of that.
It felt like he was actually interested in having a conversation. In getting to know me as a person.
That was a breath of fresh air.
After about a week of back-and-forth, he asked if I wanted to meet for coffee. Coffee. I loved that. Casual, no pressure. And if things are awkward you can leave after one cup without feeling trapped. Refreshing to hear something other than let's grab drinks, which is every guy's default. I'm not a big drinker, and I appreciated that he didn't assume I was.
We made plans to meet at a coffee spot I'd never been to. I liked that too — a sense of newness. Like this wasn't just another boring first date at the same old place.
I was excited. Nervous, but excited. There was something about him that felt different. Maybe it was that he hadn't rushed things. Maybe it was how easily we'd connected. Or maybe I was just ready for something real.
Either way, I couldn't wait to see how it would turn out.
Part 2 — The First Date, coming next.