100 Questions to Ask Your Boyfriend

By on March 1, 2014
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When you first begin a new relationship, it seems like there are a million different questions and ask and stories to share. As the relationship progresses, it is far too easy to fall in to routine. To learn more about a partner and improve an emotional connection, ladies should ask their boyfriends the following questions.

1. Do you want children?

Go past just asking this question and ask your boyfriend why or why not. The reasons behind having children or remaining childless are often more informative than the decisions on their own.

2. Have you ever gone on a blind date?

Although talking about past partners is not the best idea, blind date stories are always fun. They work as a great conversation topic because essentially everyone has a blind date story.

3. Are you a smoker?

This is a conversation to have within the first couple of dates. Some people may not mind the smell of cigarette smoke, but it can be a deal breaker for some non-smokers. Getting this topic out in the open can help prevent it from becoming an ongoing argument in the future.

4. What do you normally do on New Year’s Eve?

For good luck, couples should start the new year together. From Polar dips to the ball dropping, there are many events for dates to do together.

5. Have you ever taken a leave of absence of sabbatical?

At some point, most people want to take some time off from work. Did your boyfriend use the time for a vacation or volunteer work? Perhaps he spent it on a safari or caving in New Mexico. Whatever the answer, it is sure to say something about your date.


6. Are you ambitious? What qualities best describe you?

Go-getters and driven people may focus on their goals at the expense of other parts of their lives. If you are both ambitious, then this is not an issue.

7. Have you ever been in trouble with the law?

Barring a few speeding tickets or shenanigans during college, you should be extremely wary about anyone who has a prison record. If they seem like an upstanding individual, you can always ask for more information about their legal issues.

8. What is your opinion of divorce?

This question should wait until later in the relationship, but it reveals significant details about your boyfriend. His approach to divorce shows the amount of commitment he is prepared to make for his family and his marriage.

9. Have you ever been in therapy?

Especially in recent years, people are far more likely to turn to therapy. From emotional to psychological issues to religious questions, the advice of a counselor is helpful. Your boyfriend may not be interested in opening up immediately about these questions, but it can help you two become closer.

10. Do you do volunteer work or work with a non-profit?

After figuring out if your boyfriend does any volunteer work, you should always ask where he did it at. This is a key indicator of the ideals and things that they feel passionately about.


11. Have you ever gone to your school reunion?

For new conversation topics, girlfriends have to delve into the past. Discuss college and high school friends or what it was like to be at the reunion.

12. Have you ever had a near death experience?

Although it may not be a near death experience, a boyfriend may have had a narrow escape from death. If you have your own story, you can also share it with him.

13. How do you celebrate your birthday?

This is an excellent question to ask because it shows how much value your boyfriend places on their own birthday or holidays. If they do not remember to celebrate their own birthday, girlfriends should not hold out hope for amazing Valentine’s Day presents.

14. Are you quick to anger?

Girls have to know the answer to this before they get involved with someone. Dating a guy with an uncontrollable temper is never an ideal situation.

15. Do you like to dance?

The best long-term relationship have partners who share common interests or hobbies. A relaxing evening of dancing or night out at the clubs is a great way to bond with a partner.


16. Do you ever go window shopping?

As relationships progress, partners may run out of things to talk about with each other. From window shopping to hiking trips, learning about hobbies is a great way to get to know a partner better.

17. Can you keep secrets?

From this starting point, ladies can branch out into the types of secrets that their boyfriends keep and share some of their favorites.

18. Are you a clean or messy person?

It may not matter at the beginning of the relationship, but it will later on. If you ever move in together or get married, you will need to figure out cleanliness habits first.

19. Do you drink regularly?

Does your boyfriend drink with friends or every night? If they are a frequent binge drinker and you aren’t, you may want to keep your distance.

20. Do you think monogamy exists?

Monogamy isn’t just for penguins. Unless you believe in poly-amorous relationships, you will want to know if your boyfriend believes in monogamy first.


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