Dream Daddy

During the introduction/first day, you will eventually be able to choose the option “Go out and watch the game”. You'll go to a bar, and may or may not have a scene with Mary. Once she leaves, Robert will show up. At this point, tell him you love shots, compliment his rugged good looks, and tell him you're running from your troubles. Lay it on smooth and you'll go back to his place. Midway through, Robert will ask if you want to stop. Say no, and you'll sleep with him and unlock this trophy.

Doing this seems to help towards World's Best Dad, surprisingly.