A lot of assumptions are being made, as is in most cases on any forum or website decrying that a middle-aged man who's never had a relationship is somehow broken, or that there's something wrong with him. That may be true in some cases, but no one knows the real story until they actually ask the person.
I'm a middle-aged man in my mid-to-late 40's, and I've never had a girlfriend, but not for a lack of trying. Some of us just don't have whatever "it" is that women find attractive in a man. I'm somewhat of a below average looking bloke, losing my hair, and I could stand to lose some weight. I always wanted to have a serious long-term relationship that would eventually lead to marriage, but have always been put in the so-called "friend zone," as I seem to be best suited as a platonic friend than a romantic partner.
I have a full time job, I'm organized and responsible, I take care of my hygiene on a regular basis, I don't play video games, do drugs or smoke, maybe have a drink once a week, no tattoos, and live a fairly regular normal life. I don't think I'm boring by any means, and have a wide variety of interests in hobbies, and I'm also not one of those types of men who these days seems to be sucked into internet conspiracy theories, politics and other nonsense that's simply a waste of time. I think I have enough going for me and I'm stable enough to have a girlfriend... but here I am, and I've been single all my life, never even been on a date.
Like I stated earlier, it's not for lack of trying, but I wasn't exactly a popular kid in my school years, which made me an easy target for the girls especially to use that against me. So when any interest I had in a girl at that age, they knew how to make it hurt hard when the rejection happened. I thought that kind of thing would change in my 20's, but I was ignored and invisible to women, and was met with kinder rejection, but rejection nonetheless.
Rejection is a key part of life in general, but if all a person experiences is negative feedback to romantic endeavours, it can take quite a toll on one's mental and emotional mindset, where you start believe that you're simply unworthy and just flat out too awful of a human being to be loved by anyone else but your parents.
Now in the age of online dating, I think there's still a lot of disillusion among women that men have it easy, where in fact it seems to be the opposite, especially if you're just an average guy. I tried online dating for several years, but like what seems to be the majority of men these days, zero interest from the opposite sex.
There simply comes a point where a man just stops trying, because if you don't have the characteristics and qualities women are supposedly looking for in a mate, why waste your time? I stopped trying when I hit 40, and I've seen no difference in how women interact with me. So the idea of trying too hard vs. not trying at all is in my opinion a myth, and it doesn't matter if you work at it or the age old "if you stop looking, it'll happen" idea.
Ultimately what my ramblings come down to, is that some guys just have crap luck when it comes to pursuing love and relationships. I know that might be hard to believe for most folks, but there is a perception that there's someone for everyone, which I think isn't necessarily true, and can only make ones life worse if they follow that advice. Some people will never find someone else, no matter if they try or not, and for those who've gone decades without any sort of romantic companionship shouldn't be chastised for being a "red flag" simply because they just don't have the "it" factor in what attracts people to one another.