15. When was the last time you worked incredibly hard? Whether it's their job or a personal project, you can see what they put their heart and soul into, 16. Are you very active, or do you prefer to just relax in your free time? Find out if they are all about the gym or all about the couch. To each their own! 17. What do you do when you hang out with your friends? See what they like to do when they are social, talk about that activity if you can. 18. Who is your oldest friend? Where did you meet them? This is a great question because it often leads to some wonderful stories from when they were younger. | mean, who doesn't like reminiscing about the good old days? 19. What's the best / worst thing about your work/school? Tailor this question to the person you are talking to, whether they work, or they area student. Also, some people like to let off steam, and some like to keep it positive so you can choose which way you want the question to swing, 20. If you had intro music, what song would it be? Why? This question can lead to a good conversation about their favorite song or the music they like,