Good story.
I have a cousin....teenaged. Consistently showed up to family events in ghetto-bag outfits, unwashed, unshaven, etc etc etc.
Awhile back I asked him if he had a girlfriend. He said "no".
So, I asked him if he was gay. This time, I got a much more indignant "NO". So, I asked him what girl he thought would be interested in dating someone who looked like a homeless bum.
He's cleaned up his act a little. He's still a dumbass, but a more presentable-looking one.
You really did him a service, while it was ‘cool’ and very easy to dress like a bum; there is little that interests a young man more than a young lady.
Oh, how I wish I could travel back in time; and pull myself off to the side for a little heart-to-heart talk.