Yes you do. There is a whole quest line dedicated to seduce him, where he gets blue balled and then can't hold it anymore, afterwards you are free to have repeated content, in his or Pearls room.
I guess you got to keep extreme exploring options in the game lol I haven't gotten that option yet. It says I finished the assignment were you at home with his homework and after I finish that I got no other quest for him but I'll keep playing around with it
