During the Second date with Shaina, she will ask to play a game after calling you back and you must accept to do it now.
The game is a series of questions that test their knowledge of each other, even though they both barely know one another. The requirement is to just win and we will do so by shutting her out. Here are all the correct answers to the series of questions she will ask (This may be paired with a third successful date if you're kind and understanding with her).
After seeing the win screen your achievement should pop.