One of my readers recently shared a story about a girl who was genuinely throwing herself at him. He chickened out, and as a consequence, the girl felt rejected, which meant that he missed his one and only chance to get her. Normally, women send, at best, ambiguous signals. That one was rather forward, though, suggesting having a drink at her place, with an added wink. It is easy to imagine what could have been.

Indeed, many men have regrets about not having approached a particular woman, for whatever reason. Maybe you are on vacation and notice a cute girl at the beach. She’s smiling at you, but you can’t deal with it. As you walk past her, you think that on the way back you’ll make a move and may even, with the power of hindsight and some time to think, carefully plan out how you are going to hit on her. Yet, as you return, she is gone and you’ll never see her again. Or maybe Chad came along in the meantime and already has his dick in her. I hear that during spring break that’s a rather common occurrence.

Yet, the big problem with wistfully reminiscing about all the chances you have missed is that you make assumptions that are not at all justified. That young, sexually attractive woman may indeed be the woman of your dreams and be perfect in every imaginable way. Sure, you may as well buy one lottery ticket and become a millionaire. What is a lot more likely is that she is as vapid and untrustworthy as most girls out there. With experience, longing and regret will bother you less and less. Heck, sometimes, I wonder whether I should regret having gotten sexually involved with that many women. Most were indeed not worth my time and, overall, a negative experience. Have you ever busted a nut in a chick and lost your interest right afterward? If not, you should. Then you may find it easier to miss out on the opportunity to bang some chick because you know that after you’ve come, you likely couldn’t care less about her anyway.

Leaving the realm of the merely sexual, and looking at more serious relationships, you would likewise conclude that the women you missed out on could have been your worst nightmares. How many of your relationships went well? Your number is 0 or 1. If you are currently single, then all your previous relationships failed for one reason or another. If you currently are in a shitty relationship, your number is 0. On the other hand, if you are in a relationship that is going well, then that is your one relationship that is, for the time being, worth it. All the others were mere learning experiences at best. Numerically, you can conclude that most of your relationships were, or will be, failures.

To tackle this problem a bit more analytically, based on the previous insight, assume you regret not having approached more than one girl throughout your life. True, if it was just one, then she could theoretically have been your dream girl. However, with more than one, you can easily show that at most one of them could now be your perfect girlfriend, and that is the very best case. The others would be pump-and-dumps or failed relationships. For extra credit, you can turn this into a nice mathematical proof due to the fact that as soo as the number of girls you wish you had approached is greater than 1, the chances that one particular girl would have been worth it is less than 50%. As the number of girls increases, the probability approaches zero.

Another aspect is that you simply get older. Let’s say you regret not having taken the chance to bang that one girl back in college. Now, assume the opposite, namely that you did take your chance and she was every bit as great as you imagined. Well, too bad that she’s your age. Would you, as a 30- year-old guy, rather bang a 30-year-old chick, or someone considerably younger (and hotter)? Probably the latter. Thus, your missed chances make it easier for you, provided you do well in life, to get younger women of a higher quality because you did not settle early.

Time is quite brutal. Let me add an anecdote, a bittersweet one. When I attended university in London about a decade ago, a friend of mine was pining over some girl. She was pretty attractive: tall, slender, beautiful model-caliber face with great cheekbones. She was actually friends with me and gave me plenty of opportunities, which I did not take. Once, she invited me to a cup of coffee in the shared kitchen in her dorm and then we, somehow, ended up hanging out in her room. I had a few reasons why I did not want to bother with her. One was that I wanted to focus on my studies and not bang some chick I run into on campus every other day. Another was that I found her a bit too calculating. On top, she also looked quite old for her age. She was in her early 20s but she looked as if she was in her late 20s. Her skin was not that great close-up, and she had a lot of wrinkles under her eyes. Still, when she was dolled up, she was a real looker. She was one of the women you catch other guys turn their head for. She was not quite my type, though. Still, she was quite fun to hang out with because we had similar interests and liked the same bands.

I had a friend who had a big crush on her. He was basically salivating whenever he saw her with me. What particularly annoyed me was that he sometimes tried quizzing me about what kind of person she is, what she likes, what I talk about with her and whatnot. My suggestion that he could just talk to her he didn’t appreciate — until I got enough and just introduced him to her. It was about as awkward as you could imagine, but at least my friend didn’t have to bother me anymore. As the year went on, that girl eventually drifted away. Clearly, she was disappointed that I didn’t make a move, so why should she keep hanging out with me? My friend tried getting that girl to hang out with him, but that didn’t really go anywhere. On that note, he has a history trying to hit on girls I knew or approached, which led to a fallout between us.

About ten years later, I am not kidding, that guy sends me a message on Facebook, telling me that he banged that girl. He was boasting about it and used the most pretentious phrase I have ever read. He referred to it as “accidentally painting the Sistine Chapel.” I had lost touch with that guy about a year after graduation, so that was a most unexpected message. I heard nothing from him for years — and then he sends me that! For background, that guy has been doing very well in his career. What had happened was that she had reached out to him; she did not really get anywhere in her career, in case you were wondering. They began chatting on Facebook and a few weeks later, he flew from New York to London for a week. They hung out and quickly ended up fucking. My friend viewed this as some kind of triumph. (Nothing came of it in the end, though.) I congratulated him on his success as that was what he wanted — acknowledgment from the guy he used to look up to for his pickup prowess. I was not really that impressed by it. My interpretation is that she simply reached out to a bunch of guys online whom she met over the years. Since my friend is now balling, he was a good mark. On a side note, when I looked her up afterwards, I noticed that she had “un-friended” me on Facebook in the meantime. I guess I didn’t make the cut in terms of economic success.

Another issue is that the supposed triumph is not really one if time has been wearing down your idols. Banging your university crush when she’s in her early 30s and desperate for a guy with a fat wallet is downright pathetic. It reminded me of how some boxing champions, after retiring, make a comeback and end up getting knocked out in the first round by some third-class brawler. The woman in that anecdote I pity, but the guy is about as bad. Can you imagine fawnining over some chick for a decade, and then you end up banging a ten-year older version of her who looks nothing like how you remember her? Is that guy blind? It’s like eating leftovers from a stranger’s plate.

I also had it happen to me that some women reached out to me on social media, many years after I had met them. The most egregious case was a girl I went to school with until grade 6 or 7. She was the most attractive girl in class and she often hung around with me. Too bad she entered puberty years before me. Some of the other kids were teasing us; looking back, I wouldn’t be surprised if she had wanted some dick even back then. Well, I had completely forgotten about her. Yet, about twenty years later, she tracked me down on social media and emailed me, sending me a bizarrely long message. She wrote that she’s so happy to have found me, asked me how I have been, and tells me her life story. I had to think for a moment who that person was. All I saw was not a pretty woman but a pretty fat woman with heavy makeup on. But even if she had been slim — what’s the point? She thinks she can just reach out to a bunch of guys she’s met throughout her life, hoping to reel some sucker in. It’s a Hail Mary. Those women seemingly try to seduce guys with the memories they have of them as if she had remained young and beautiful in your memories. That you could have completely forgotten about them or that they are no longer good-looking does not seem to even register as a possibility for them.

Those unique chances you’ve missed were not worth it, based on how unsatisfying dating is. Worse, you had your chance at a particular point in time. Even if you could, you will not recreate that opportunity. That does not mean that any of those women will not reach out to you in the future. Should you pursue that path, though, you will only get disappointed. Your just punishment awaits. It is poetic justice: you did not make use of the chance you had to get with the young, attractive woman, and in the future, she may haunt you as a hag. On the other hand, if you had banged her when you first had the chance, you would have moved on eventually. By taking your chances, you consume women when they are more attractive, and because you have discarded them once, they will not try to hunt you down when they are old, fat, and ugly and desperate to secure a provider.

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