“Regret about not doing something.” When my great-grandfather was alive, he gave me that advice. He never regretted doing something, no matter how bad it turned out. It was the “what ifs” that he regretted.

So, like my great-grandfather, when you’re looking back at your life from the vantage point of being in your 90s, is it worth taking the risk on a potential relationship?

Would you regret not taking the risk?

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How Not to Regret a Potential Relationship

Here are the three things to consider.

1. Anxiety. Do you overthink almost everything? It may not be the woman that you’re interested in–it may be you. Be honest with yourself. If this is a trait you exhibit for most things in life, start by learning more about yourself, with the next step being a therapist who can help you. (I’m in no way connected to or paid by the author of the linked book).
2. Faults. No one is perfect. Look past her flaws and focus on what’s good about her. Unless she has a significant problem (for example, alcoholism), if her good traits significantly outweigh a few faults, it’s worth your time to see if there’s a spark. You could end up in a fulfilling relationship. 
3. Readiness. Many people think the timing needs to be perfect to start a relationship. Like so many things in life, perfect is something to strive for, but if you’re waiting on ideal timing or a perfect situation, you’ll regret it. It’s just not practicable. If there aren’t significant red flags, give her a chance. Worse case, you’ll have a good story to look back on and to learn from with no regrets.

At first read, this article may seem negative. But I wrote it intentionally that way to bring out the positive in you! If you have others, you’re welcome to send them to me, and I’ll post an update.