Here's tonight's findings:
I opened up a random old game in Sunset Valley, found a human sim and got her employed at the Gypsy Caravan I placed in town. I sent her around town asking sims (all human) for their signs. I got to 7 sims and still no badge. The only factors I can think of is that she was a level 1 writer and I had her quit that job for the new one. And after I started playing her I found out she was pregnant. So she hasn't actually been to work at the Caravan yet because of her pregnancy.
I opened up another old random SV save and grabbed Blair Wainwright to test this badge with her. I decided to wait to ask sims for their signs until after she had been at work for one day. But of course the next day turned out to be a Holiday so she had the day off. And I've got to get to bed so I couldn't wait around for her to see what happens.
I never thought this would be such a hard badge. :D
