PEWDS! I FOUND THE SOLUTION TO ACTUALLY COMPLETE THE DATE!! You have to buy a gift, and give it to him once the "line" is completed - you can do 1 or 2 fails for the questions. And then take a selfie and the "heart". Right after that you will get a puzzle. There's 2 puzzles in each "date-maps" so you have to collect them all. I don't know further cuz I haven't tried. - Brofist