Frisky Business (UP)

The trivia game is part of Jenny's "dating" line and can be played in Chapter 9 but only after you have already earned Giddy Up. You will need to play the Trivia game to get Puppy Love as well, since it will earn you an additional "get it on" after the game is done. She will ask you a series of questions and which each correct answer, she will remove an article of clothing. You need to get the first four questions right to unlock the trophy.

If you are following the Roadmap, this trophy is part of Run #3. The Walkthrough for this can be found here.