Life is a journey. It will not always be the way it is now, it will change because that is what happens... So now it's about helping direct where his life will go. For some reason society values "popularity" of one kind, but the truth is, people can be happy in lots of social and interpersonal configurations.
Be ready for disinterest and rejection, but also be ready for interest and acceptance and even attraction. Cuts both ways.
I don't think it's bad to reach back out to old friends to see who is still receptive to a phone call or after dinner meet up now and then. In fact, that's what my 40s are like now--quiet, occasionally meeting new people who have time and interest for me and vice versa, and occastional base-touching with the old crowd. It's lovely and calm, actually. I love not feeling like I have to pretend I liked social butterfly buzzing. I always thought it was exhausting!
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