Random Questions to Ask Your Boyfriend

20 Random Questions to Ask Your Boyfriend

You know his favorite color, food, and video game, but there is more to a relationship than just that! We’ve come up with a list of 20 fun, serious, and flirtatious questions to help you get to know your boyfriend better and to help you grow your relationship. But don’t just stop with these, come up with a few personal questions too! As women, I think we are all guilty of talking a little excessively sometimes, now it’s his turn to talk. So start asking!

1What was your first thought when we met?

If you met your significant other at a party you don’t quite remember or while digging your retainer out of a trash can this might be a question for you to laugh over. But, it also gives him the perfect opportunity to make an embarrassing or seemingly dull event into something sweet.

1. What was your first thought when we met?

2If we could go on a dream vacation together, where would you take me?

If your dream vacation is a tropical beach and his is hunting in Alaska, you might not know each other well enough. This question can also be a fun dreamy idea to talk about together or, if you are in a serious relationship, create a real goal for you to work toward.

2. If we could go on a dream vacation together, where would yo…

3What are your career goals (what do you want to do when you grow up)?

For a relationship to work your long-term goals have to be compatible. You can’t be an advocate for the environment while he works for a giant oil company, both in this situation could loose credibility. Location also plays a part in this question.

3. What are your career goals (what do you want to do when you…

4If you had to pick a different first name what would you pick?

This is a super fun question that can really make your partner think. How many times is someone asked to choose a different name… not many. If he answers with a name you weren’t expecting, ask why!

4. If you had to pick a different first name what would you pi…

5What is the best gift someone has given you?

He could really open up to you with this question, or show you how important different items are in his life. What a person classifies as a gift can range from a present wrapped with a bow or an inanimate gift like the love you give him. Awe!

5. What is the best gift someone has given you?

6What was your first job?

If your man is the fun, jokester type this could be the perfect ammunition for you to mildly poke fun at him. “Oh so you where a fry cook huh? Bet you could show that kid behind the counter how it’s done!”

6. What was your first job?

7What is your favorite home cooked meal?

Go ahead and call your mom to see how it’s done. This is for the next time he has a horrible day. You can surprise him with his favorite, delicious home cooked meal. Home cooking is the original comfort food.

7. What is your favorite home cooked meal?

8What is your favorite holiday?

If he loves Mardi Gras or St. Patrick’s day you know he loves to party. If he is a Fourth of July or Thanksgiving with the family kind of guy it is easy to tell where his priorities lie.

8. What is your favorite holiday?

9Describe yourself in 3 words.

How he see’s himself is important for you to know. He could respond sarcastically and that would give you both a good laugh, but if he is genuine with his answers this could be an issue you could help him with. If he describes himself as shy and conveys that he thinks that is a negative quality, you can help him come out of his shell!

9. Describe yourself in 3 words.

10Describe me in 3 words.

It’s likely he is going to use beautiful/pretty, smart, and funny, but it’s still nice to hear your man say positive things about you. This one is solely for your benefit. However, if he doesn’t answer with those three typical answers listen to what he’s saying. If you don’t agree with how he responds there could be a problem.

10. Describe me in 3 words.

11What are you most insecure about?

It is a big deal when guys open up to you about their insecurities. All men want to be the strong, supportive ones in the relationship and for a man to take down that wall and let you in is a big deal.

11. What are you most insecure about?

12Have you told your parents about me?

This question’s meaning depends on how long you have been together. If you have only been together for a week, he may not be at a place where he wants to let his parents in on his relationship. However, if you have been together awhile and he has yet to tell his parents about you he might not be as serious as you are.

12. Have you told your parents about me?

13If you could have a super power, what would it be?

This is just a fun, conversation starter of a question! Everyone wishes they had a super power at one point.

13. If you could have a super power, what would it be?

14What is your biggest pet peeve?

This is just good to know for future reference. If his biggest pet peeve is when someone says “like” to much, you may want to watch this when you are talking to him.

14. What is your biggest pet peeve?

15Dinner and a movie or a picnic and stargazing?

This is a good indication if he is an outdoor man or more of an indoor person. If you both agree that a picnic and stargazing is a little to sappy then you found your man. But, what girl doesn’t want to go on a romantic picnic just once?!

15. Dinner and a movie or a picnic and stargazing?

16What physical feature do you find most attractive about me?

Again, this is a question for your enjoyment! Compliments are always great. When he answers be sure to tell him that you love when he compliments you, maybe he will pick up on the hint and do it more often.

16. What physical feature do you find most attractive about me?

17What subject where you best at in high school?

And don’t let him answer lunch! Is he an analytical thinker (math, science) or a creative thinker (English, drama, art). This is a great question to get to know how a person thinks and operates.

17. What subject where you best at in high school?

18What’s the thing you most regret?

Depending on how comfortable he feels talking about it, you may or may not get an answer. Don’t push him to answer this question if he doesn’t want to talk about it. Showing him that you respect his privacy is a big deal in relationships too.

18. What’s the thing you most regret?

19Are you more connected with you mom or dad?

If he is a momma’s boy you know he will treat a lady right, but expect to be taken care of too. If he is more connected with his dad he might now be so great at noticing your feelings or emotions. This could be a good point to keep stored away if an argument ever arises, he may not have any idea why you are upset.

19. Are you more connected with you mom or dad?

20What could I do better as a girlfriend?

In relationships, both parties have to give 100%. You both need to hear the other’s needs, and be able to listen without letting your own emotions interfere. Flat out asking what you could do to be a better girlfriend is a great way to make your relationship stronger.