100 Questions to Ask Your Boyfriend

61. What is your longest romantic relationship?

Even if he has only dated girls for a few weeks at a time, it does not mean that he cannot have a long-term commitment with you. It does mean that he will have to learn how to behave in a relationship and may need a patient girlfriend.

62. Where do you think you will be in five years?

More importantly, do his goals and dreams coincide with yours? If he plans on moving to Argentina in five years, a long-term relationship may not be in the cards.

63. What are the five major drawbacks to your personality?

This question helps you know which traits to watch out for and can inform you about any worries that may occur in the future.

64. What accomplishment are you proudest of?

Discussing top accomplishments indicates what your boyfriend values and his goals in life. It also shows how dedicated he is to following through on his plans.

65. What body part is your favorite in the opposite gender?

For a casual conversation topic, bring up favorite body parts.

66. If you could go on a vacation anywhere in the world, where would it be?

From Europe to Latin America, there are many desirable places to visit. Where has your boyfriend traveled to? Does he want to visit some of the same places as you do? If money is a factor, the two of you could save up until you have enough money to travel somewhere together.

67. When was the last time you truly laughed?

Sometimes, people become too focused on day to day life and forget to enjoy themselves. If your boyfriend has not truly laughed for a while, it may be time to watch a comedy movie or turn on your favorite comedian. Taking some time out to relax and enjoy life is important for every relationship.

68. What has been your most exceptional act of charity?

It does not have to be just a financial act of charity. Perhaps your boyfriend regularly volunteers with his church or local food bank. If the project sounds interesting, you could try doing it together.

69. What is the dumbest thing that you have ever done?

Life does not have to be entirely serious. Sharing embarrassing or stupid moments is a way to connect emotionally.

70. If you could meet one historical figure, who would it be?

Discussing favorite historical figures helps to show you who is role model is in life.

71. What do your parents do?

The answer to this question may show how he lives his life. Did he earn his way to the top through hard work or parental influence? It also may show the type of world he grew up in.

72. What are your political beliefs?

Bring this topic up carefully because politics can be an emotional topic. People with strong political beliefs can quickly develop heated arguments.

73. What is the most expensive gift you have purchased for someone?

Is your boyfriend the generous type? Does he like to plan out each gift with loving care? Use this question to get to know him better.

74. Do you read newspapers?

Some people like to read the newspaper every morning over a cup of coffee. In recent years, more people turn to online blogs and news sites for their information.

75.What is the most adventurous thing that you have ever done?

If he hasn’t had a major adventure yet, you could plan a new adventure as a couple. From outdoor exploring to traveling abroad, there are many different ideas available for couples that can help heighten the excitement in any relationship.

76. Do you like pets?

Some guys love pets while others can’t stand them. Before you start planning on a future together, figuring out if you will ever have pets or children is important.

77. What did you spend the summers doing as a child?

Perhaps he went to some of the same summer camps or vacationing in the same areas. Once a relationship has started, it may be surprising to find out all of the missed opportunities you had in the past for meeting each other.

78. What are the five biggest strengths in your personality?

Personal opinions are never strictly based in fact. The five biggest strengths in his personality may not be his actual strengths. Instead, they are the traits that he feels are most important about his personality. This slight psychological insight is extremely informative.

79. Who is your favorite author?

If you love reading, you will want a boyfriend who does as well. Even if he isn’t interested in the same genres, sharing favorite authors can be fun.

80. What would you do for a living if money were not an issue?

What we want to do in life is often far different than what we actually do in life. The need for money and a stable income means that your boyfriend is pulled away from the artistic life or personal business that he initially wanted. Finding out his original dreams may be insightful about what matters to him.