100 Questions to Ask Your Boyfriend

41. Would you rather live in the city, a small town or out in the country?

Even though most people have to live close to their job, understanding where your partner wants to live can help you make plans for the future.

42. How long do you spend on the Internet each day?

Plans for craft nights or weekend outings may be stymied if your partner spends their evenings playing video games or surfing the web.

43. If you could change one thing that happened in history, what would it be?

Individual choices for changing historical events can be illuminating. It shows what he values and his favorite moments in history.

44. How many lovers have you had?

Although this may not be the right conversation for a first date, it should occur before any sexual encounters. Before you have sex, you should also ask when was the last time he was checked for sexually transmitted infections.

45. If you won a million dollars, what would you do with it?

It may not be a likely event, but it is always fun to dream about what could happen. How would he spend the money? Would it be on his family or a bunch of toys?

46. How often do you see your parents?

Unless his parents live far away, this will serve as an indicator of his familial relationships. If he visits his family frequently, it will show that he has a close relationship with his parents.

47. What causes do you believe strongly in?

From environmental projects to political activism, the causes he believes in show a great deal about who he is. When you are both interested in the same causes, you can always spend a few dates volunteering and working toward a common goal.

48. At what age did you start dating?

Unless he dated without his parents knowledge, this question indicates some of the family values he grew up with. Strict parents tend to have children wait longer before dating while a lax household may not have had any rules in place.

49. Are you afraid of heights?

In addition to asking about his fear of heights, you may want to ask about what he is afraid of most in life. This will help you become closer and can prevent any mishaps. If he has a fear of dogs, you will be able to avoid interaction with pets and will know in advance that your house will never adopt a dog.

50. How romantic are you?

This question helps you to figure out your expectations from the relationship. Although most relationships are not just wine and roses, knowing how romantic he is can help you learn what to expect.

51. Are you a member of any society or social club?

Is he involved in a fraternity or does he spend his time in social activism groups? Where he spends his free time is highly informative about what he believes in and his personal habits.

52. Are you a virgin? When did you lose your virginity?

Even if he lost his virginity early, it does not signify that he is a player. Many people who grow up in difficult situations end up losing their virginity earlier than normal.

53. How patient are you? Would you describe yourself as a patient person?

Discussions about personal habits and attitudes can help you decide if you are right for each other. If you share many of the same quality traits, it can improve the quality of your relationship.

54. Do you have any addictions?

You should also ask your boyfriend if they have had any addictions in the past. If they are currently in NA or AA, you should avoid dates at bars so you do not make their sobriety difficult.

55. Are you a people person or do you like to spend time alone?

Social butterflies like to be around people constantly. If you like to spend the evening at home, it could lead to arguments or unhappy evenings at parties in the future.

56. What is the largest loan you have ever obtained?

It may not matter at the beginning of the relationship, but you need to know where he stands financially if you plan on getting married or living together. Many divorces stem from financial arguments, so you both have to have a stable financial situation before taking it to the next level.

57. Are you afraid of ghosts?

Although superstitions are gradually disappearing from Western culture, some old beliefs still remain. Even if he is not a full believer in ghosts, this could be an interesting conversation to have. Trips to haunted houses or camping trips spent sharing ghost stories could be enjoyable.

58. When was the last time you cried?

If he admits to crying, it is a sign that he is emotionally open and honest. Once you have this conversation, find out more about what caused him to cry and why.

59. Do you tell lies? When was the last time you did so?

When the answer to this question is yes, you should take it as an early warning. If he tells you that he lies frequently, you cannot expect total honesty in your relationship.

60. Who is your favorite celebrity?

It may not be extremely informative, but talking about movies or favorite celebrities can help you get the conversation flowing on a first date.