Between The Matches

When I left Jack’s apartment that morning, I didn’t feel great.

The truth was, there were a few things that had been bothering me for a while, and after weeks of pushing them aside, they were becoming harder to ignore.

For one, I wouldn’t have called what we had a relationship in front of him.

Jack had been burned a few times while dating, and the idea of committing to something so new made him nervous. He told me that every time he introduced a woman to his friends or family or got excited about someone, things seemed to fall apart shortly afterward.

Ironically, that fear was becoming a self-fulfilling prophecy.

He had only recently mentioned me to his family after our last date, and I couldn’t shake the feeling that we were already heading toward the ending he seemed so worried about.

The bigger issue, though, was compatibility.

The chemistry between us was undeniable. That part had never been the problem.

But as I got to know him better, I started wondering if we were actually a good match long-term.

Jack loved music.

I loved sports.

He worked as a school counselor.

I worked in construction.

Those differences weren’t necessarily bad. In fact, I enjoyed learning about the things he cared about. But when I looked beyond the attraction, I wasn’t sure how much overlap there really was.

And this is where I may lose some of you—and that’s okay.

If I had met Jack anywhere other than a dating app, I probably would have assumed he was gay.

To be clear, there is absolutely nothing wrong with that.

The best way I can explain it is that he had a much more traditionally feminine personality than the type of man I had always pictured myself with.

For example, I use a skincare brand called Tatcha, and one day he asked if I was a “Sephora girl.” I didn’t even know they only sold it at Sephora, but he did.

At one point, we even stopped at Sephora so he could browse for a particular (expensive) body wash he wanted.

Most of his closest friends were women.

Meanwhile, I was the opposite.

I worked in construction.

I hung my own shelves.

When something needed fixing, my first instinct was to grab a tool.

When Jack needed something hung in his apartment, he hired a handyman through an app.

There was nothing wrong with any of that. It simply wasn’t what I was looking for.

And I think deep down, I knew it.

Part of me wondered if I was being too critical, but I couldn’t forget that the last time I overlooked my reservations and pushed forward anyway, it eventually ended in divorce.

Without thinking much about it, I sent him a text later that day about not loving how the morning had gone.

His response caught me off guard.

He immediately became defensive and pointed out that I hadn’t said anything in the moment.

The frustrating part was that he was right. I should have communicated better.

But at the same time, I didn’t feel like he was willing to hear me out either.

The conversation fizzled out without much resolution. When it ended, I think we were both left feeling disappointed.

And maybe a little turned off.

---

Labor Day weekend arrived, and I headed out of town. Jack and I still talked, but the conversations became more sporadic.

Life was picking up for both of us. Football season was approaching and work was picking up which took much of my time. He was back at work and settling into the school year.

The space between us grew naturally.

Neither of us said it out loud, but I think we both knew where things were headed.

Still, weeks earlier I had promised him I would come see his band play when they had a local show.

I texted him to ask if the invitation still stood.

His response came back immediately.

“Of course.”

So that Friday night, my cousin and I met in the parking lot and headed inside.

The band was already halfway through their first set.

We grabbed seats at the bar, and every so often Jack would glance over, smile, and wave between songs.

Each time, I smiled and waved back.

I remember feeling relieved. I didn’t want things to be awkward.

During the break, he made the rounds saying hello to coworkers and friends before eventually making his way over to us.

He introduced himself to my cousin and then gave me a small hug.

As he leaned in, he kissed my forehead.

Looking back, I realize I unintentionally dodged a real kiss.

At the time, I didn’t think much of it.

We chatted for a few minutes before he headed back to the stage.

When the night ended, my cousin and I started making our way out. Jack met us near the door.

We hugged goodbye.

Again, he settled for a kiss on my forehead.

Again, I didn’t really notice what I was doing.

Neither of us asked if the other wanted to hang out afterward.

Neither of us made plans for the next day.

The truth was, the relationship had already ended.

We just hadn’t officially acknowledged it yet.

Before I left, he told me to text him when I got home.

I did.

He never replied.

---

The next morning, I woke up to a text from Jack asking if we could talk.

I already knew what the conversation would be.

Neither of us needed to say much.

We agreed that we were better off as friends.

And honestly?

I think we were both right.

To this day, we’re still friendly.

He has a girlfriend now and seems genuinely happy.

I’m happy for him.

Looking back, I can’t imagine a better person to have been my first date after my divorce.

It didn’t work out, but that doesn’t make it a failure.

Jack was kind. Patient. Respectful.

He taught me a lot about dating, communication, and what I was looking for in a partner.

In many ways, it was the closest thing I’ve had to a real relationship in the last year.

(Spoiler alert. Sorry.)

And despite how it ended, I wouldn’t change a thing.

Sometimes people come into your life forever.

Sometimes they come into your life to teach you something.

Jack did exactly that.