How Overthinking Led To The Demise Of My Relationship

by Jordyn Wegner
Julien L. Balmer

I am an overthinker.

There: I said it. The first step is admitting you have a problem, right?

I've been overthinking things my whole life, always dissecting every possible scenario to the point where it's held me back from potential experiences... more specifically, potential relationships.

I'm not one to have regrets in life. I don't like to look back and wish I had done something else.

But there is one relationship I always seem to go back to and wonder, "What if?"

I was traveling through Europe a few years ago, when my travels led me to Copenhagen, Denmark. My friend and I were visiting over New Year's. When we realized the whole city had shut down on New Year's Day, we decided to check out the bar in our hostel and meet new people instead.

One group of travelers at the bar stuck out to me: They were six guys from Canada. Since I'm also from the great white north, it was nice to hang out with fellow Canadians.

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There was one guy in particular who caught my eye, and we hit it off instantly. We spent the whole day talking and laughing together. Then, before we knew it, it was early the next morning, and the bar staff was shutting everything down.

I had never felt such an instant connection to someone. I even commented later on that he could have been my soulmate. I gave him my number at the end of the night, confident it wouldn't be the end.

Sure enough, it wasn't.

When our time in Copenhagen was over, I went back to the UK, where I was living at the time. He, on the other hand, continued to travel.

We kept in touch and talked every moment we could get. When I wasn't working or he wasn't sightseeing, we were getting to know one another.

I could talk to him about anything and everything. I felt like I could truly be myself with him.

We did the long-distance thing for six months. He finally went back to his life in Canada, but my year overseas was coming to an end. Once I was back in Canada, we'd be much closer to one another... a two-hour plane ride, to be exact.

I knew the next step was to see one other in person again. But this is where the overthinking began.

I asked myself every single "what if" there was. What if we see each other in person again, and the feelings aren't there? What if the feelings are there?

If things got serious, would I move to his city, or would he come to mine? What if he starts resenting me for having to leave his friends and family if he moves here?

What if I'm not ready to give up being single? What if there's better out there?

What if? What if? What if?


I overthought things to the point where I had essentially talked myself out of the relationship. I had gone through every scenario there could possibly be, and focused more on the potential negative outcomes than the positive.

I was afraid of the unknown, and I just didn't want to have to deal with the scenarios I made up in my mind. I slowly distanced myself from him.

So, eventually, things ended.

Since then, he's moved on. He's met a new girl who seems really lovely. They've moved in together, and they have two dogs.

I have moved on as well.

There's no point dwelling on the past. But every now and then, I ask myself, "What if?"

What if I had not asked so  many "what ifs," and just let things be?

What if?