Instructions
Find a character on the "Thrillville: Off the Rails" game that you are interested in dating. The idea of a date in the game is to walk off with that person; the game does not let you go on an actual interactive date.
Add the selected character to your friend list, and interact with the character until you have your friend's happiness set at "Maximum." You will need to talk, play minigames and flirt with the character to raise the happiness level.
Select "Flirt" in the interactions menu once your friend has his happiness level at "Maximum." If your friend is happy enough, he will walk off with you, holding hands.