After things ended with Jack, I found myself back on Hinge.
That’s where I matched with a guy we’ll call Ryan.
Full disclosure: Ryan is only getting one blog post.
Not because he was a bad person, but because he didn’t play a particularly significant role in my dating journey.
When we first started talking, I thought he was great.
Our conversations flowed naturally. We texted throughout the day, and he seemed to check a lot of the boxes I was looking for. He was funny, responsive, and easy to talk to.
A few days before our first date, he asked if we could FaceTime.
“Of course!” I texted back.
Then I immediately rushed around trying to figure out what to wear and make myself presentable.
The call came through, and while Ryan looked exactly like his pictures—and was definitely attractive—something caught me off guard almost immediately.
His voice.
Call me shallow if you want. Maybe I am.
But there are certain things that affect attraction, and for me, the way someone speaks is one of them.
There wasn’t anything wrong with his voice. It just didn’t match the image I had built up in my head from our conversations.
He came across much goofier than I expected.
We talked for quite a while and I genuinely enjoyed getting to know him, but I would be lying if I said my excitement level didn’t drop a little after the call.
I still wanted to meet him.
I just wasn’t quite as optimistic as I had been before.
A few days later, we met at a bar halfway between our towns.
We happened to pull into the parking lot at almost the exact same time.
The first thing I noticed when I got out of my car was how tall he was. I think he was around 6’4″. And to be fair, he was cute.
We hugged hello and headed inside.
The conversation was decent. Not amazing. Not terrible. Just… fine.
At some point, the topic of my divorce came up.
I had already told Ryan about it while we were texting, but he wasn’t shy about wanting more details.
“So I think it’s something I can look past,” he said. “I just want to know a little more about what happened.”
I knew going into dating that my divorce might be a dealbreaker for some people.
But to this day, Ryan is the only person who ever made me feel like I needed to explain it.
I thought for a moment before answering.
“I tried everything I could to make it work,” I said. “The reality is that marriage takes work, and my ex-husband didn’t understand that. I once asked him if he would rather look happy or be happy, and he told me he’d rather look happy. If I had a fake smile on my face for the rest of my life, he would have been okay with that. And at twenty-nine years old, I just couldn’t accept that being the rest of my life.”
The conversation moved on from there, and we finished our drinks.
When the night ended, he walked me back to my car.
We shared a quick kiss goodbye. Just a peck. And I headed home.
I want to pause here and make a point that becomes important later.
There is a difference between leading someone on and getting to know them.
Could I tell after the first date that Ryan probably wasn’t my person?
Most likely.
But I also wasn’t interested in dismissing someone after meeting him once.
I had just started dating again. I was learning. I was figuring things out. And I genuinely believe people deserve a fair chance.
A week later, Ryan and I met up again to take a walk at a nearby nature preserve.
The walk itself was nice.
The conversation was… interesting.
Mostly because Ryan spent most of it telling stories. Lots of stories. Some were funny. Some were entertaining.
Most had absolutely nothing to do with anything.
For example, I learned that one of his former neighbors had won the lottery.
Did I need to know that information?
Not particularly. But I learned it anyway.
That weekend, Ryan invited me over to watch Monday Night Football.
We both enjoyed football, and I was still trying to determine whether there was something there worth pursuing.
When I pulled into his driveway, he opened the door before I even reached the house.
I brought dessert. He kissed me hello.
And that’s when things started to go downhill.
You learn very little from a quick peck goodbye. A real kiss, however, tells you a lot.
Unfortunately for me, what I learned was not encouraging.
Ryan was thirty years old. And somehow kissed like a teenager.
There were teeth.
There was chaos.
There was absolutely no rhythm.
At one point I genuinely felt like I wasn’t getting enough oxygen.
It was, without exaggeration, one of the worst kissing experiences of my adult life.
We sat on the couch watching football, and he attempted to move things forward physically.
The problem was that the more we kissed, the less interested I became.
Nothing felt natural. Nothing felt comfortable.
And by the end of the evening, I was actively looking for an escape route.
When he stepped away to use the bathroom, I made up my mind.
As soon as he returned, I stood up and announced I needed to head home.
I may have used an excuse involving my time of the month.
Was it my finest moment? Probably not. But I never claimed to be perfect.
I awkwardly escaped his goodbye hug and practically sprinted to my car.
To be clear, Ryan didn’t do anything inappropriate.
He wasn’t disrespectful. He didn’t make me feel unsafe. The chemistry just wasn’t there. At all.
Over the next few days, I became more distant. I knew I wasn’t interested anymore. The challenge was figuring out how to say it.
Eventually, I decided honesty was the best option.
Me: Hey, can we talk?
Ryan: Yeah sure. What’s up?
Me: I’m just going to be honest. I’m not really feeling this. I think we’re better off as friends. I’m sorry.
Ryan did not take it well.
He responded with a lengthy message explaining that people should know whether they like someone after the first date and accusing me of leading him on.
At first, I felt bad. Then I felt frustrated.
Then I got angry.
The entire purpose of dating is getting to know someone.
Sometimes attraction grows.
Sometimes it disappears.
Sometimes it takes a few dates to realize someone isn’t the right fit.
As soon as I knew I wasn’t interested, I ended things. But I refuse to apologize for giving someone a fair chance. Everyone deserves that.
In the end, Ryan and I stopped talking completely. There was no friendship. No occasional check-ins. No happy ending. Just a somewhat sour ending to a very short chapter.
Looking back, Ryan taught me an important lesson: giving someone a chance is not the same thing as leading them on. Dating isn’t about making a decision after one night—it’s about learning who someone is. Sometimes that process leads to a relationship, and sometimes it simply gives you clarity. And as long as you have the right intention, you’re doing okay.
Between The Matches 
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