You need to defeat tristan few times. He is a dude who shows up on wednesdays in lategame. First on mall, then on beach and lastly on the street.
After you progress further on Anna's Starmaker ( 4 Hearts ), you will get to meet Tristan at 3 different location each week. First will be at the Mall ( Wednesday ), Second will be at the Beach ( Wednesday ) and the lastly at Downtown Street ( Thursday ). I forgot the exact sequence of answers you have to tell him each time so I'll just list them below:
1. Who are you?
2. You choose young women because they are vulnerable
3. Lonely is the keyword here
4. I'm grown up enough that I don't need constant reassurance
5. My role model is my Dad
6. Jesus man, get a grip
7. Where are your bitches?
8. They're not your real friends then
9. Talk to REAL people