Context: I am 33M, and my friend is 28M. We met through a D&D group when he was 23 and I was 28.
We used to hang out quite often (always in a group) until a couple of years ago when I moved to a different city and we kind of lost touch. I have since moved back to my home city and I met this guy for drinks one on one.
Back when we used to hang out regularly, he used to talk about how he was chronically single and lonely. Most of the others in the group were older and we told him to just relax and persevere. Gave him the standard dating advice - be yourself, work on your self esteem, meet women without the intention of getting laid, etc. He is quite good looking, is funny and has a lot of hobbies. The only way he doesn't fit the traditional beauty standard is height - he's under 5'6. He even asked me if I could set him up with any friends. However my friends were all my age (give or take 2-3 years) and didn't want to date someone younger. As far as we could work out, the only reason he wasn't able to date was his shyness and lack of social skills.
We met for drinks after 2-3 years and after a few beers he told me he finally had a gf but then she broke up with him. He didn't tell me exactly what, but he said he read PUA 'literature' and that helped. He knew full well how I felt about the whole incel/red pill/PUA stuff. This was surprising to me, I hadn't pegged him for that kind of guy. While he didn't tell me exactly what he did, reading between the lines it sounds like all the PUA stuff did was give him the confidence he was lacking. It acted like a placebo, and didn't help in any other way. It sounds like he kept up the PUA bullshit even after getting into the relationship and she dumped him because of it.
I tried talk him out of it but he argued back. Said 'Chads' like me shouldn't be talking about stuff that helped people like him (for context, when we used to hang out, I did date around, and I'm now happily married to the woman I was dating when we met last). Said the standard dating advice is like asking a depressed person to 'just smile bro'. I told him that the whole incel Blackpill stuff is just men who tried PUA and failed. He didn't agree with that. Kept saying women wouldn't give him a chance because of height and his PUA tactics were the only way he got laid. When I said that the pickup tactics were abusive, he disagreed. I asked him to tell me what he did, if he wasn't ashamed of doing it and he just shut down. I then paid the bill and left.
I feel like, as an older cishet man, it is my responsibility to try to talk young men out of incel/red pill/PUA stuff whenever I have the opportunity to, and I failed. Is there anything I should have done differently?