100 Questions to Ask Your Boyfriend

81. Do you like children?

Even if you aren’t planning on having children any time soon, you don’t want to be in a relationship where one partner wants children and the other hates them. Ask early on so that you aren’t surprised in the future.

82. What is your favorite sport?

For the nerds and non-jocks out there, alternative activities like book clubs, video games or bowling may be a better topic.

83. Do you like partying or throwing parties?

If you like to party or if you hate it, you need to have a partner with similar tastes. Spending your weekends alone while your boyfriend is drinking at keggers is not part of the ideal relationship.

84. What is your idea of the perfect evening?

Remember how he answers this question. In the future, you can plan a date around his idea of the perfect evening.

85. What is the worst thing you ever did to a friend?

You may have to wait for the relationship to progress for a few months before you delve into his deepest and darkest secrets. Be warned—if he has done something terrible to a close friend, you can expect any breakup to be difficult.

86. Do you enjoy traveling?

Learning his likes and dislikes can help you to make plans as a couple. You can figure out if long distance traveling or local camping trips are the best choice for your vacations.

87. What books have influenced your life? What is your favorite genre?

Childhood favorites like Ayn Rand or Harry Potter resonate far after they were first read. For an intellectual and engaging conversation, books are a great place to start.

88. What was it like growing up?

Once you get past the basics of your personalities and likes, you and your partner should begin sharing information about your home life. Specifically, discuss stories that shaped your childhood and the place you grew up at.

89. What is the best compliment you were ever given?

It may not be the most riveting conversation, but sometimes discussing compliments can bring up interesting stories from the past.

90. What would you do if your friends didn’t like your girlfriend?

This can be illuminating. If you haven’t met his friends yet, it could be a sign of what is to come.

91. What do you think your best achievement in life has been so far?

If he hasn’t been able to accomplish a great deal, you can always talk about your future dreams. Perhaps you both want to start a business or write novels. Some of your goals can be worked on together.

92. What is your relationship like with your parents?

Before you meet the family, you should understand what their relationship is like. You may also want to learn more about his parents in advance. This will help you to prevent any missteps.

93. Do you think that the father has to be the head of the family?

In the past, traditional families were set up with the father at the helm and the wife in the kitchen. Since the 1960s, more families are headed by women and the nuclear family is no longer the norm. Before you ever consider marriage, learning what your boyfriend expects and telling him what you expect is a vital step.

94. What has been your favorite vacation to date?

If you are considering a vacation together, thinking about past vacations can help you decide. When you can’t decide between which trip you want to take, you can always flip a coin. The losing vacation can be taken next time.

95. What is your earliest childhood memory?

Sharing family stories is a great way to grow closer as a couple.

96. What is the highest academic degree that you have earned?

This can lead into other conversations like favorite classes or college majors.

97. What was your relationship like with your mother and father growing up?

Although daddy’s girl and momma’s boy are the stereotypes, it is not always the case. Before you meet the folks, learn about the type of relationship your boyfriend has with his parents.

98. What is your favorite movie? Is there a movie that you enjoy watching over and over again?

Movies are a safe subject for first and second dates. Everyone has seen one and always has an opinion.

99. When is your birthday?

It is a basic question, but extremely important. Take note of his birthday so you do not forget it.

100. What is your favorite thing to do on a date?

If you are taking him out on a date, you will have to know what he likes to do. From outdoor adventures to moonlit walks, knowing what he is interested in can help you to craft the perfect date.

By leaving questions open-ended, you can help get your boyfriend to talk. You have to keep in mind which part of the relationship you are in before asking a question. Sensitive topics like politics and religion may have to wait until you know your partner better.