When you get popular enough on Starmaker, you'll start meeting a douche with two women in the mall. Give him the right answers and he'll look bad in front of them. He'll then leave and come back in another location when your popularity has hit the next threshold. Once again, give the right answers to properly shut him down and he'll flee. After that you'll see him all depressed and lost in a final location. Give him some useful advice and you'll get the trait.

Tried to give you a nudge without too many spoilers. It was incredibly satisfying when I managed to complete the questline, particularly because it actually has potentially two rewards. One of said rewards are an alternative solution in case you don't spot the code for the safe in the dude's office, which was another thing that had me incredibly frustrated until I spotted the truth of the four numbers completely by chance.