Except that sometimes talking with someone doesn't yield any results aside from "I dunno", "whatever", etc.

They're looking for the piece that says "here's an attractive idea" that gets that someone involved.

Sometimes I have a similar issue with my son. It's usually as simple as saying "here's what we're doing this weekend" as opposed to getting the brick wall response to "what do you want to do this weekend?" of "I dunno."

There are tons of different websites that offer "Things to do in ____" but most of them are so spammy. Something that was personalized based on your preferences/interests, or based on a group of people's preferences, would open up a lot of doors.