Knowhow-Now Article

100 Questions To Ask Your Boyfriend

By Linda Brown

Linda Brown

Have you considered making a list of 100 questions to ask your boyfriend? Just making such a list can shed light on your relationship. You probably will start to delve into what you want to know about him, but never really thought to ask. You will also think of questions that are pretty zany. Still, making a list of 100 questions to ask your boyfriend can be helpful in furthering your relationship.


Remember that guys don’t like to “chat” as much as we gals do. So, don’t be annoyed if he doesn’t want to answer all 100 in one sitting. But asking 4 or 5 on each date can elicit the kinds of responses you want. Alternatively, send him one question by email or text each day and let him respond that way.

What should be on your list of 100 questions to ask your boyfriend? One of the primary issues is his background. Asking questions like where his parents met, when his ancestors came to the United States, his parents’ occupations, what his relationship with his siblings are can all provide valuable information on how he views family life.

don't be afraid to ask questions

Money may be a tough issue to bring up directly, but in your 100 questions to ask your boyfriend, you can approach the issue indirectly. Ask him how his parents viewed money, whether he would rather have a high paying job with low satisfaction or a low paying job with high satisfaction. Query him on his feelings toward charitable contributions. Ask whether he would rather have a lot of stuff or a full bank account.

You can also ask him about his career. Ask him about his college major, his plans for graduate and professional school, his feelings on the relationship between education and getting a job. Ask what his favorite and least favorite jobs he’s ever held were. Ask him to tell you the job he has the most and the least respect for.

Think about the future when you formulate the 100 questions to ask your boyfriend. For instance, how many children would he like to have? What is his approach to discipline? What kind of education – public, private, or home school – he sees his children having.

You should also ask lifestyle questions. Where would he most like to travel? What one experience would he most like to have? Does he have an appreciation for any type of art? How often does he like to spend time with the guys? How much and how often does he drink?

If you are serious about the guy, sexual issues should make up some of the 100 questions to ask your boyfriend. For instance, how many sexual partners has he had? Has he ever had a sexually transmitted disease? Does he believe in monogamy? How does he feel about porn? Are there any sex acts that make him uncomfortable?

The point of the 100 questions to ask your boyfriend is to open the dialogue in your relationship. As you begin to ask and answer these personal questions, you get a sense of whether this relationship is destined to work over the long run. That’s the value of the questions.


Ask him about his college major, his plans for graduate and professional school, his feelings on the relationship between education and getting a job.

talking is always useful

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