40 Questions to Ask a Guy on a First Date

21. What is your favorite book? Do you enjoy reading?

If you are looking for an intellectual, this question could reveal a lot. For ladies who want a down-to-earth fellow, a potential video game player or fitness jock could be a positive thing.

22. How long ago did you end your last relationship? How long was it?

If the date has been going well, you can begin approaching more serious matters.

23. What do you normally do with your friends for fun?

Find out before it gets serious if he is a couch potato or a workaholic.

24. How old were you when you developed a first crush?

Was he “mature” for his age or a late bloomer?

25. What are you currently saving money for?

This tells you two things: what is important to him and if he is capable of saving money.

26. What do you have in your fridge right now?

An empty fridge is a sure sign that he is still stuck in the frat house mentality. If he is an adult, his fridge should look like it.

27. What do you consider to be your happy face?

Essentially, you are asking him where he feels the most comfortable and happiest.

28. When were you born?

This question is an easy way for astrology lovers to see if they have found that perfect Aries-Taurus match.

29. Do you believe in aliens? Or ghosts?

It may sounds silly, but it is always interesting to find out what other people believe in.

30. Is there a job that you would never be able to do?

If he just says no, he is lying. Everyone has at least one job that they would never want to do and this job reveals a great deal about their dislikes.

31. Have you vacationed out of this country? Where have you traveled to?

This is another way to ensure that you both have the same interests and world views.

32. What is an unusual fact about you?

Learn if he spends his time doing handstands or volunteering at a children’s hospital.

33. Are you a major sports fan?

If you are worried about losing your boyfriend to Monday night football…then basketball…and then baseball every week, you should start by asking this question.

34. Out of every job that you have had, which one was the worst?

This can signal his ability to hold down a job and how prideful he is. If he was willing to take a job as a mascot to pay for school, he is most likely a modest, hard-working guy.

35. If you could go to any point in history, what time period would you choose?

To start with, this will indicate if your date knows anything about history—and if they read up on history often enough to care about what time period they’d travel back to.

36. What has been the greatest achievement of your life to date?

Whether you are dating a 20 year old college kid or 40 year old divorced dad, this question can reveal a great deal about what he has done with his life so far. It also shows which parts of his life he considers to be the most important by what he states is his greatest achievement.

37. If you won the lottery, what would you choose to do with the money?

It may be a common question, but it can be a fun way to liven up the date.

39. What is one of your family’s traditions?

Asking your date this question can help you figure out what type of family life he had while he was growing up. It can also reveal how close he is to his family in the present day.

40. What are some of your top pet peeves?

Everyone has particular behaviors, attitudes or issues that they hate. Discover in advance what his pet peeves are. If the pet peeve is extremely abnormal, you can always ask him to explain how it began.