The Biggest Sex Regret of My Life
This is my L story.
The biggest sex regret of my life happened over 20 years ago.
While I’ve made many mistakes in my sexual escapades before and since this single regret has haunted me more than any of the others.
If I could go back, I’d change it in a heartbeat.
This is my biggest sex regret.
The Biggest Sex Regret
It may or may not surprise you that my biggest sex regret happened during my college years.
This huge, haunting regret also occurred the first time I had penetrative sex. I say “penetrative” because I consider oral sex to be sex. Apparently, not everyone does.
But I do, so that’s why I mention it.
Here is how the regret took place: I was at a German party during my third year at university. After drinks and music, everyone sat in a circle and passed around a joint.
I was beyond lit.
During the entire night, I flirted with this older German girl.
At some point, she said, “Don’t make me like you.” Which told me she already did.
By the end of the night, we left together back to her place. I was still completely out of it but making my own choices. At her apartment, we ended up having sex, after which I spent the night.
The entire experience was embarrassing.
First of all, I didn’t have a freaking clue what I was doing. I was a sex octopus, just flailing around trying to get something right.
It didn’t help that it was dark and I was slightly drunk.
If all of that wasn’t terrible enough, I didn’t know who she was. I still don’t. I saw her once, but not close up, and I never spoke to her again. And not because I’m a dick.
I didn’t have her name, phone number, or address.
Why It’s My Biggest Sex Regret
All in all, it wasn’t a terrible night or garbage fire experience — so why is it my biggest sex regret?
That’s a great question.
The reason I loathe this experience so badly is that it was my first “time.” I gave away my V card with such disregard and insignificance. It is like I took a heaping crap on a million-dollar bed.
For me, the flippancy is what boosts this regret above all others.
Even above the time that I got kicked out of a country for having sex on a mountain (I wrote an article about that somewhere :).
There is also the fact that I can never undo it. You never get a second chance at your first time.
“By three methods we may learn wisdom: First, by reflection, which is noblest; Second, by imitation, which is easiest; and third by experience, which is the bitterest.” — Confucius
What I Would Do Differently
If I had a sex time machine and could travel back in time, I’d for sure change a few things.
I wouldn’t just go back to that night in college.
Heck no, I’d go back way further, to my junior year in high school. That was the year my parents had a 23-year-old German exchange student live with us for the summer.
We ended up messing around, and she wanted to have sex with me, but I was terrified of getting her pregnant or catching an STD back then.
While we never dated, I did spend a few with her (she lived with us, after all), and I did like her as a person.
Fast-forward a few years into college, and I might have still slept with the unnamed older girl at the German party, but the sex would have been better and the entire experience not encased in significance.
How I Handle Sex Regrets
We all have regrets.
Things we wish we had done differently, said differently, or any number of other things. And while it’s natural to dwell on these things and beat ourselves up about them, it’s not productive and can actually make us feel worse.
So how do we deal with our life regrets?
One thing I do is to try and reframe them in my mind. Instead of thinking of them as failures, think of them as learning experiences.
“I made decisions that I regret, and I took them as learning experiences… I’m human, not perfect, like anybody else.” — Queen Latifah
I ask myself, “What can you learn from the situation that will help you in the future?” This doesn’t mean that you should dwell on what went wrong, but rather try to take something positive away from the experience.
For my big sex regret, I now view sex with more significance.
As I’ve grown older, I’m much more selective with who I sleep with — all the way down to 1 person now, since I’m currently engaged to my stunning fiance.
Another way to deal with life regrets is to simply let them go.
This can be easier said than done, but it’s important to remember that dwelling on regrets is not going to change the past. It’s only going to make you feel worse in the present.
I’ve learned that you must forgive yourself, move on, and focus on the future.
Whichever method you choose, remember that life is too short to spend dwelling on regrets. Learn from your mistakes, process your past pain, and give yourself permission to move forward.
Final Thoughts
To be honest, if I was able to use a sex time machine, I’d probably end up with a few more high school stories, and maybe an unplanned kid or three.
It’s probably for the best that none of that happened.
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