40 Personal Questions to Ask Your Boyfriend


Dating is fun but at some point the desire to have a long-term relationship may develop. When that feeling strikes, some issues and topics must be brought to the table. Talking about such issues while the relationship is still young may save the both you a lot of trouble. For instance, it will help you determine if your partner values your presence in their life.

There are a myriad of questions that plague the mind of a girl about her boyfriend’s past, present and future life. Chances are some questions may have been asked in the past, but satisfactory answers were missing. It is a known fact that men are not comfortable answering some queries, especially on issues they consider personal. Some men will lie to protect you, and other will outrightly ignore them.

Be warned ladies, you may not like some of the responses. As a matter of fact, they may even jeopardize your relationship. Tread with caution. On the bright side, it will help you understand his fears, goals and plans in life, his likes and dislikes, strength and weaknesses and most importantly the position you hold in his life.

There are so many questions that can be asked.  Here a list of 40 personal questions that a boyfriend can be asked.

  1. When is the first time you told me “I love you”?

Girls would be excited if a guy gives the correct response to that question. In most instances, the girlfriend knows the date, time, place and circumstances under which the declaration was made.

  1. What made you fall in love with me?

Human beings want to feel appreciated. Asking your boyfriend what he loves about you may trigger some memories. It will also let you know what characteristics he adores in you.  Show him that his answers flatter you. Give him the assurance that you love him too.

  1. Could you ever forgive cheating?

This question is used to gauge his reaction towards infidelity in relationships. However, it should be used as a get out of jail free card in the event one cheats in future.

  1. Do you have any regrets in life?

Everyone has regrets in life. We all wish we did something differently. However, the response given should be not used in future as a reference point. If it still hurts, show him.

  1. What is the most courageous thing you have ever done in your life?

When he tells you of that heroic act he accomplished, praise him endlessly. It will greatly boost his ego and earn you some extra love.

  1. What is your ideal vacation?

Based on the answer given, you can surprise him on his birthday by taking him there.

  1. What do you like about me?

Most ladies will ask this question in a bid to know what aspects or characteristics about them excite their partners. He will probably list the positive attribute that he loves about you. It may be that killer smile or your kind-hearted nature.

  1. What is your favorite book/movie/author?

Asking him what books he loves or his favorite movie will give you a peek into his life. Who knows, you may surprise with a book or movie that he adores. In addition, it may give you an insight on how literature has influenced his life.

  1. Is it ok if I hang out with you and your friends?

Ask this questions if you are not sure how he feels about you hanging out with him and the boys. Do not automatically assume that he would you having out with them.

  1. What song makes you happy?

Knowing his favorite song may earn some points in future. For instance, once you know the song, you can play it when he is sad or on a date. If possible, learn the lyrics to the song and sing for him once in a while.

  1. Have you ever had a one night stand? If you did, do you regret it?

A lot of caution should be exercised while asking this question. Some men may not be comfortable sharing that kind of information. In addition, any information he shares should be kept between you.

  1. Do you have any opinions about politics/religion?

The answers given to questions on controversial topics such as religion and politics will reveal his opinion towards the subject in question. You do not have to share similar opinions. No judgment should be passed.  Respect his opinion.

  1. Do you have any hobbies?

Understanding what he loves to do in his free time may strengthen the relationship. If he loves swimming, you can accompany him one weekend and spend some quality time together. You may be surprised that you may have a common hobby.

  1. Have you ever experimented with legal/illegal drugs?

This is a question that is usually asked out of curiosity. If he has done illegal drugs in the past, do not use such information in case an argument arises in future. Tactfully, ask him what made him do that.

  1. Do you think the past matters in a relationship?

Most guys may not feel comfortable answering this question. If he does not want to answer, do not push him. If he thinks the past matters, avoid bringing matters of the past such as mistakes made and ex-girlfriends as that may escalate conflicts.

  1. What has been an embarrassing moment for you?

The level of embarrassment is relative. What may be embarrassing to one person may be a hilarious situation to another person. Based on the answer given, do not make fun of him especially if he has a sensitive nature.

  1. What are some of your goals in life?

When you feel that you are ready to settle, ask this question. Compare his goals and yours. This will help you determine if the future is certain.

  1. Do you see me in your future?

This kind of question should be asked when he shows some interest in spending the future with you. However, one can tell if the guy is serious or not.

  1. Do you like to have children one day?

Only mention children when you are sure you can build a future together, if he is not for the idea of having and loving kids, do not force the idea on him.

  1. What is the most crazy/weird thing you have ever done?

Whatever response he gives, laugh it off and do not use against him in future, especially in negative situations. If it was nothing serious, you could ask if he is comfortable trying it again.

  1. What would you change about me if you could?

He may probably point out a few flaws about you. Try not to get mad and improve on the flaws if you can.

  1. Why did you break up with your first girlfriend?

Avoid doing whatever may trigger a break-up. For instance, if the ex cheated, you will automatically know that he hate cheaters.

  1. If I got pregnant, would you still stay with me?

If you are a sexually active couple, this is a question that must be asked. However, most guys will automatically say they will stick by your side so that they can save their face. The golden rule is, however,  to take precautions at all times.

  1. How would you define a good sexual relationship?

Only ask this query if you and him are open about sex. For those who are reserved on matters of sexuality, it may rub them the wrong way. Ask him what he thinks about foreplay and different sex positions, as long he is comfortable discussing it.

  1. What did you think of me when you first met me?

He will basically highlight aspects that made him be attracted to you. Gladly, take his responses as a complement. His answer will give an insight of the opinions he holds in regards to you.

  1. Do you have any close female friends, other than your female family members and me?

Some girlfriends may feel bothered if their man had many female friends. Ask this question if you feel the female friends in his life may jeopardize your relationship. Boundary setting can be done at this point.

  1. Is this relationship short or long term?

The answer given to this question will determine if your relationship has a future.

  1. What is your opinion on an exclusive relationship?

Based on his answer, you will determine if he is monogamous or polygamous.

  1. Do you think we can love each other without any physical intimacy?

Not all boyfriends equate sex to love or consider sex as an important aspect of a healthy relationship. For others, sex is an important ingredient in a relationship.

  1. How often do you need or expect sex?

If your boyfriend is crazy about sexual relations, ask this question and see if you can deliver. Pray and hope your libido levels match.

  1. Do you consider yourself good with money?

If you intend to spend the rest of your life together, learn how he manages his funds. Ask him about his financial obligations, his opinion on saving and spending and how much earns among other questions. However, not many will comfortably answer such questions.

  1. Between your family and friends, who do you consider important?

Let him give his response and reasons for selecting whoever he considers important.  Ask him what he thinks about your family and friends too.

  1. If you had one wish, what would it be?

Who knows that you might be the one to make it happen? If the wish sounds a bit silly, do not laugh at him.

  1. Describe your ideal girlfriend (excluding the physical characteristics)?

Do not get mad if his description does not fit your bill.

  1. What bad habit would you like to break?

Maybe he smokes, swears a lot or bites his nails

  1. What do you think of being forever together?

Only ask this question if you are sure he is the one. Whatever his response is, respect it.

  1. Would you ever consider moving in together?

Maybe he loves his personal space and privacy. Do not force the idea down his throat.

  1. What would be the best reason to break off our relationship?

The answers provided will give you a clue as to what may be the potential causes of a breakup.

  1. Have you ever committed a crime?

Maybe he stole or got arrested for doing drugs. Pass no judgment.

  1. What are some of your weaknesses?

Men consider themselves strong. It may difficult for him to open up to you. If he does own up, do not make fun of him. In addition; do not mention them when he errs in future. It will bruise his ego.