I don’t know how applicable this is for you, but if this were someone close to me, my first question would be what’s good for the other person.

In most cases, if they are happy and getting on in life, and are able to take care of themselves, I’d let things be.

That said, the tension from your framing is between “leave good enough alone” and “personal growth and a fulfilling life”.

Healthy relationships, especially with a partner, are one of the better things about life. They are also incredibly difficult to get right without practice.

So, is your friend lonely, or are they happy to be alone?

If you intuit it’s the former, then AI is palliative care which runs the risk of creating a dependency.

It is also possible that the right set of prompts, perhaps something which incorporates CBT, would help them learn more about themselves and challenge beliefs or responses that are no longer useful.

And if your friend is just happy alone, then you can disregard the rest.

Thanks, I much agree. The impression I get is that he isn't "happy" and would rather a real relationship, but has completely given up on that at this point and is kind of trying to be happy with the little he has. He hasn't directlly said that, but that is what I would most bet his feelings are based on what he has said.

Ultimately I want him to be as happy as he can be, so if this is the way then I'm happy for him. I guess for me the real hard thing is deciding how I should react when he talks about this sort of thing. I don't want to encourage him if I'm doing him a disservice, but I do want to encourage him if he really is better off with it. Being neutral as I am now feels like it might be the coward's way out, but it's also more true to how I feel since I really don't know whether it's good or not.

Really appreciate your reply, thank you