I got that the first time too - won the award, not the guy.
Don't know if this is what happened to you, but you have to visit him a lot in his office to get the scene where you can make the choice that gets you the best ending. Don't know if scenes you get elsewhere also impact it, but I got the best ending by restoring back a couple of weeks and visiting him every single day everywhere he went. You know, as you do in healthy relationships. :D