The man I have been dating has the same perspective as the OP. The player’s life can be lonely, empty & meaningless. But for men who haven’t reached player status it’s romanticized and sought after to such a degree that men who haven’t been there won’t believe you.
They can’t. They don’t realize how other people will use the player for their own aims, they don’t know that pursuit of sexual pleasure for pleasure’s sake deprives you of meaningful connection with another human being, and they are short sighted.
I’ve known many players over the years personally as friends. I married one & I’m seeing one now almost 2 years in.
Today my BF was telling me about his best friend. The best friend is tall, great looking, successful and a good man. He’s in his early 50s and has no issue attracting women. He’s so over endless rotations of plates. He has no companionship, nobody who knows his “story” as Paul Zanka would put it, no wife, no kids, etc. His friends have families and meaningful relationships in their lives and his friends don’t have meaningful time to spend with him because they have more fulfilled lives with their family.
He is disillusioned. A man I know is in the exact same boat. He’s a retired professional athlete, successful, handsome & great looking...mid 50s as well, and also a lifelong bachelor. Exact same feeling about his life. Like he’s missed the boat chasing pleasure and missed out on meaning. It’s sad. That time is gone for good. But 20 years ago neither one of these men would have thought this is how they would feel in their 50s.
My guy is seeing that same writing on the wall. He worries about growing old alone. Even though women flock to him. He has few real friends. My ex husband struggles with it too. Same thing. Loneliness and few friends & waning desire to endlessly chase women.
Maybe it’s that men hit the wall roughly 10 years later than women...but age comes for us all eventually.
I like what Jordan Peterson has to say on the subject. Seek meaning instead of pleasure...but pleasure is a most seductive pursuit, so it’s tough when the disillusionment sets in.
I noticed you used the word "meaning" and its accompanying adjectives six times in this post.
There is nothing inherently meaningful about a marriage or LTR, nor is there anything inherently meaningless about short term flings, casual sex, or serial dating. I've had flings and ONS that meant more to me than some LTRs, at least in different ways. You get what you give - usually.
I think you can derive "meaning" from either, though I think happiness is what we really should be extracting from our choices and pursuits.
And what you're describing about your friend feeling as though he "missed the boat," that's the human condition. The road less traveled. Had he gotten married at 25 and stayed faithful, he'd probably be wondering about all the women he missed out on in the prime of his adulthood. FOMO is what advertisers use to separate us from our money. It's powerful but futile; we have to live with the choices we make.
To quote Rollo, "I’ve never had meaningless sex; I meant to bang every woman I’ve ever banged."
The broader point is that whether they're looking for flings or marriage, putting the cart before the horse is a fool's errand, to mix a couple of cliches. If your friend, and BF's friend, really had such a miserable time slaying chicks all those years, perhaps there was something missing from within, rather than from the women and relationships they were pursuing.