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I was nice to him most of my playthrough, except in a few places, and still got it.
If you befriend both Charlie and Violet, you will not get the achievement even if you act kindly to Olivia and do not smash the radio. What you want to do instead, being friendly to Violet and Olivia, but NOT with Charlie (let Jacob bully him, etc.).
Also I got both 'Hurt Healed' and 'Take Care of Athena' achievements on the same playthrough. So you are not necessarily need to choose Riley to go through the portal in the end to get 'Hurt Healed'. When Jacob went in, I still got both achievements. (Also Jacob never even asked me to be friends, so I guess I just ignored him a little too much lol)