Do you have some dating and mating regrets? Are some of them huge regrets? I certainly do. I’m going to share mine so that you can see that you’re not alone or use them to avoid making the same mistakes.
It’s easy to look back on things and decide whether we should have moved forward on something or not. When we’re faced with a choice, there are always a bunch of unknowns. That’s why many choices involve risk. When it comes to dating and mating, quick decisions are frequently required. A few allow us time to consider our options, like marriage, but most require prompt action.
Here are my biggest dating and mating regrets.
Not attempting to connect with a girl who I found extremely attractive.
This started in grade school. I attribute my lack of assertiveness to being young, shy, and naive. But later in college and during my corporate career, I passed up a few opportunities as well purely out of fear. I felt that I didn’t have a chance with her. I found out later that this is often not the case, but rather fear messing up my perceptions.
I have long since gotten over the fear of rejection. However, there are still occasions when I’m not in the zone and it gets the best of me.
Passing up a perfect opportunity at my 20-year high school reunion.
Second chances are rare. Like many people, my second chance came at my 20-year high school reunion. Here’s the story.
I had a serious crush on a beautiful dark-haired girl in elementary and middle school. I lost track of her when I was sent to a boys’ home in the eighth grade. Although I returned to my hometown high school in my senior year, I did not see her again until the night of my 20-year high school reunion.
Everything in my life was nearly perfect at the time. The only problem was that I was perusing a woman who couldn’t make the decision to be with me. I regret devoting so much time to her to the point that I passed up this and other opportunities.
I had a senior management position at a well-known international corporation and I arrived in my company car (a hot sports car) with a reservation for a room at the luxury hotel where the reunion was being held. Although I had everything in place personally for such an event, the strangest thing happened when I entered the party. I felt just like I did when I returned to public high school. I felt totally out of the loop socially since I’d been away at the boys’ home for so long. It was awkward.
When I noticed that dark-haired girl, and now a woman, from across the room, she looked the same as I remembered. She had obviously taken very good care of herself. And I later discovered from the “post” reunion publication that she was single and living locally.
I greatly regret not approaching her that night. Although she was continually engaged in conversation with different men and women throughout the night, I had learned not to let that stop me. But it did that night.
I suspect that my failure to approach her was connected to my insane loyalty to a woman who was choosing another man over me and feeling totally out of place with people I’d known since elementary school.
Staying loyal to women who choose not to be with me.
A perfect example of this is what happened at my 20-year high school reunion. I was being foolishly loyal to a woman who had chosen not to be with me. I now know that this was a waste of time. Far too many other people will likely be a better match to worry about one who isn’t into you.
Here is a related story with some twists and turns.
Just before I was sent away to the boys’ home in the eighth grade, I was romantically involved (kissing a lot, but no sex) with the first love of my life. Part of the reason I was sent away was because my very strict stepfather banned me from seeing her. I found out a few years before his death that he thought we were taking drugs and that her parents were a bad influence. I knew nothing about drugs at that point and both her parents were middle school teachers!
The only way I could see her was to runaway, which I did a few times. I was also driven to leave because my mother and stepfather were constantly fighting — literally every day.
The price I paid to see her was three years in juvenile hall and a boys’ home. Fast forward about 14 years. I’m a district manager for the same company I mentioned before. I’m on a business trip in South Lake Tahoe (I know, it was nice. 🙂 ) and I was checking into the best hotel in town. The person standing behind the front desk to check me in was the girl (now a woman) from eighth grade.
After quickly getting reacquainted, we agreed to meet in my room at sunset and drink some wine. (She got me a room overlooking the lake.) I do not remember what led up to it, but I found myself lying in bed while she stood next to it removing her clothes. I still don’t fully understand what came over me, but the memories of all those years of yearning for her and hearing about her sexual adventures suddenly hit me and I became angry and said, “All the waiting was not worth it! I do not want to do this.” You may be thinking that my reaction was pretty cold. If so, you are right. I could have handled it better.
I apologized to her the next morning when I checked out. We did see each other a few times after that, but we were never intimate which was extremely rare for me at that time.
I regret sacrificing so many years for a girl/woman who was out of reach for a variety of reasons. Strangely, I also regret not sleeping with her.
I believe our guidance system for dating, mating, and love comes from our intuition (or gut instincts) and not from our head. These signals can lead us to what is best for us and help us to avoid bad situations. The key is learning to recognize and trust these messages.
If we rely too much on what our head is telling us, our thoughts and logical intentions begin to be infiltrated by our fears. Go with your intuition. And go forward anyway even if you are afraid. Soon after you’ve done this, your fear will dissolve and be replaced with certainty.