It might be questions to get to know them better on an intimate level or just really PG rated questions to see if the two of you are a good match! You might like to ask questions about his family, his previous relationships or just random fun questions about life – the choice is entirely yours. Simply, make a list of the 21 questions you would like to know about your SO and they will do the same about you. What I love most about this game is how simple and easy it is. If you think gee I would really like to know X but don’t know the right way to go about asking – put your question as one of 21 questions, make it a fun game and he will be none the wiser – trust me! How to play 21 questions with a guy? These questions are equally quite fun in a group of friends. This is such a fun game as you really can know your date partner on a deeper, more intimate level. Try 21 questions to ask a guy if you want to get to know someone better or alternatively if you are already in a committed relationship and want to dive further into the deep and meaningfuls together.