Between The Matches

Before I get into the rest of this story, there is something I want to talk about.

One thing nobody really prepares you for when re-entering the dating world is the conversations around sex, safety, and expectations.

When I was younger, relationships always seemed to progress naturally. You met someone, spent time together, and things developed organically. There wasn’t much discussion because there didn’t need to be.

Dating today feels different.

Relationships can be more casual, timelines are less defined, and people often assume things without actually talking about them. Because of that, conversations that might feel awkward are probably more important than ever.

Looking back, I’m grateful that Jack brought up the topic of being safe. Part of it stemmed from his own anxiety, but it opened the door for a conversation that needed to happen. It was mature, honest, and something I appreciated more than I expected.

While Jack was away at his brother’s bachelor party, I continued spending time with Chris.

Over the weekend, we spent an afternoon at his apartment pool, went out to dinner, and I stayed the night.

I was having fun.

That was never the problem.

Chris was kind. He was thoughtful. He treated me well.

But lying in bed that night, I couldn’t avoid a realization I had been trying to ignore.

We weren’t compatible.

I kept hoping maybe it was something that would develop with time. Maybe I just needed to get to know him better. Maybe the chemistry would grow.

Deep down, though, I already knew.

Sometimes there isn’t a major issue.

Sometimes nobody does anything wrong.

Sometimes two people just aren’t the right fit.

That realization was difficult because I genuinely liked him as a person.

But it was there, whether I wanted to admit it or not.

Sunday night finally arrived, and Jack was on his way home.

Apparently, he was just as eager to see me as I was to see him because we made plans to get together the same night he returned.

I made my signature dish—chicken parmesan—and headed over to his apartment.

We ate dinner, swapped stories about our weekends, and laughed about everything that had happened during his trip.

Then, naturally, we ended up watching more episodes of Tires.

Some things were becoming routine in the best possible way.

That night, I stayed over.

And honestly, it was every bit as good as I had hoped it would be.

The next morning, I woke up before Jack and set up my laptop in his living room to work remotely.

About an hour later, he finally emerged from the bedroom to get ready for work.

What surprised me was how grumpy he seemed.

Not angry.

Not upset.

Just grumpy.

I teased him about not being a morning person, but something felt a little off.

Jack was a school counselor and one of the most emotionally aware people I had met. He was usually excellent at expressing what he was feeling.

This time, though, he brushed everything off. Maybe it was nothing. But I noticed it.

After he left for work, I headed home and finished my day.

That night, I had volleyball and, afterward, stopped by Chris’s place.

By this point, I knew a decision was coming.

The physical connection with Chris wasn’t developing the way I had hoped, and the more time I spent with him, the more certain I became that my feelings weren’t growing.

I didn’t know exactly when I was going to end things.

But I knew I would have to.

At the same time, I was dealing with something much bigger than dating.

The sale of my house was dragging on.

The divorce terms had finally been settled, and all the paperwork had been signed, but the house remained. Most afternoons were spent sorting through years of belongings, deciding what to keep, what to throw away, and what to donate. I also spent a considerable amount of energy trying to avoid my ex-husband whenever possible.

It was emotionally exhausting.

No matter how exciting dating felt, there was still a very real part of my life that was ending.

And endings are rarely simple.

In the middle of all that stress, Jack continued to be a bright spot.

One afternoon, he took me to his parents’ house. He showed me his drum set and taught me a few basics. He introduced me to the outdoor cats he cared for. He showed me the places and hobbies that mattered most to him.

There was something special about seeing someone in their element.

For the first time, I felt like I was getting a glimpse into the life he had built before I came along.

Later, I took him back to my place at my brother’s house.

We grabbed food and eventually made our way back to his apartment.

This would be the last time I saw him before he left to spend a few weeks with his parents in Myrtle Beach.

Before he left, we decided to start watching the Harry Potter movies together.

The fact that he had never seen them felt absolutely criminal.

I took it upon myself to fix that.

While Jack was away, most of my time was spent cleaning out my house or spending weekends down the shore.

Chris and I saw each other less and less.

Not because of an argument.

Not because either of us had done anything wrong.

But because I had already arrived at the truth.

As much as I liked Chris, I knew I wasn’t going to choose him.

It was only a matter of time before I had to say it out loud.