I can't even find the interaction. Closest I can find is Share Personal Life Goals. I practically became best friends with the grocer in one go trying to find the interaction. If it is the Life Goals one then yeah it's not counting for me either. If that's not it, is the interaction actually called Ask About Dreams?
I play in Chinese so I didn't know what is it in English, but you need to scroll down the "Friendly" interaction tab, usually in the end, a specific interaction to talk about dream.
I had been trying to complete this one too. The only option I ever got was "talk about dreams" (you have to be inspired to get that option). My mistake was that I invited the grocer over to the lot I was on, and even though his profile still said he was a grocer, the title after his name (when you mouse-over) was gone. I went to town and waited around until another grocer showed up, in the delivery uniform. It had the job title in red along with his name and I got the option to ask about his dreams as soon as I introduced my sim to him. It had the same little waving-guy icon that you get for other tasks.
