How Do You Know You’ll Regret It?

I see a lot of memes flying around that look like this:


While I do agree with the gist of these sayings – no one wants to look back on their life and wish they had done this or that – but how do you know at the time that making a decision will equate to regret or not? What if, either choice that you make, both roads lead to some kind of regret?

I suppose this isn’t really making much sense without an example…

In my last year of high school I met a boy. He liked me, I liked him, there was a lot of eye-locking across the school grounds during breaks, a lot of flirting, and a lot of showboating. Despite the fact that we were clearly into each other, neither of us did anything about it, i.e. ask each other out on a date.

I graduated and not saying anything to this boy was my biggest regret. I thought about it all the time, wondered if I had asked him out we would be together right now; it was the kind of crush that was all consuming.

Eventually my best friend at the time got sick of me feeling so down about it and made me call, which was terrifying as I lived in the time of not everyone having a mobile – I had to try my luck ringing the dreaded home phone.

Long story short: he said he liked me too, we dated for about 3 months (summer romance cliche) and then we broke up (and my heart got broken cliche.)

Now that I am older and wiser – it was 10 years ago now (holy heavens, that makes me feel old!) – I sort of look back at that whole situation wondering if I did the right thing.

I know that if I hadn’t asked this boy out, I would regret it because I would never have known what could have been.
At the same time, wouldn’t it be nice to look back and think of the mystery of it all? I would have this great memory of a time when I could love with everything I am and not have it muddied up with all the horrible things like the panic attacks and having my heart broken via cheating.

Truth is, I would prefer to think of this guy the way I did while I was still at school, rather than the way both he and I acted in the short-but-sweet relationship. In hindsight it was more damaging for my self-esteem and heart than if I had just left it to be “what if.”

I guess what I’m trying to say, rather inarticulately, is don’t always think that you’ll regret not doing something. Sometimes saying no or denying an open door isn’t the worst thing you could do.





2 thoughts on “How Do You Know You’ll Regret It?

  1. I get this. I had a similar thing happen. Though the boy and I never dated I did get to know him. My regret was him opening his mouth. My best friend and I fawned over him all the time. Then we got to know him after we graduated and found out he was an idiot. I guess it’s like meeting a celebrity and breaking the idea of the person. Sometimes those ideas are worth so much more. Especially for creative types. I think we can run a thousand life times with someone through our wads before even finding out their names. It’s like the first page of book… It holds so much possibility and sometimes that’s sweeter. Hope that makes sense.

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