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Set aside for a moment the superficial details (rap music, tattoos), your in a strange town with a child, in a vulnerable position-(pumping gas) when approached by one of several strangers-(out numbered) and asked a seemingly innocent but anachronistic question-(possibly being "interviewed") so you move yourself in a position to access your firearm and assertively deny being "James' friend".
Based on those facts I would say moving to condition orange was reasonable and you handled it well.
I guess there are a few possibilities:
1. You looked like a friend of James and they wanted to introduce themselves and enjoy the warm glow of a mutual friendship
2. You were being assessed as a target or perhaps a threat
3. They were there to meet someone for a "deal" of sorts and the "friend of James" was just code

Now if this had been a group of church ladies or something, all the other details would remain true but only you can say for sure if your alarm would have gone off