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So first, use it as a means of speaking to everyone. You'll usually only get one response, and there's no chance of handing out gifts. But if you say hello to everyone, chances are you'll catch the people you've missed, before.
(sorry for necroing this thread, btw
Keep in mind that anytime you talk to anybody at 1.) festivals 2.) if you GIFT something to someone, 3.) if you are trying to PURCHASE something like over the counter or 4.) Cutscene that triggers without "talking" to someone = NONE of these count as "meeting" people. I really thought this was a glitch and was going to give up until I just went back and talked to everyone again. I missed Gus, who I had both gifted something to him and purchased something from him, but never "talked" to. Try all this stuff first!
That used to be the way, but I think they changed it in the last update.
It's happened to me twice and it was with people that you got a cut scene with before you introduced yourself. They registered on the relationship tab but didn't count towards the achievement. Mine were Willy (fishing scene doesn't count) and The Wizard (turning up at his place by request doesn't count).
I'd think of people you haven't really approached outside of cut scenes and try them out.