201 Questions and Things to Talk About With Your Boyfriend (How to Get to Know Him Better)

Q: How can I entertain my boyfriend over text?

If you want to entertain your boyfriend over text , consider playing 21 questions with him. Ask him about his favorite movie, the book that made him cry, or what makes him the most nervous.

Last updated on June 4, 2022 by April Maccario

Some people can find it hard to open up in a relationship and may need some prompts. Get the conversation going and talk about things that you may never have before by playing 21 questions using the questions below. This is the perfect way to get to know each other more intimately.

Some guys may talk about themselves without any help, but others need a little prompting. If you want to talk about deeper topics with your boyfriend but don’t know where to start, use these ideas below and see where the conversation ends. You may learn things about each other that you may never have otherwise imagined.

Contents

1 Things To Talk About With Your Boyfriend
2 FAQs
3 To Sum Up…

Things To Talk About With Your Boyfriend

What name do you now hate because someone you once knew that you didn’t like had that name?
What confuses you every time someone mentions it?
What is the worst thing that you have ever eaten?
What is the hottest thing that you have ever eaten?
What is the nicest thing that you have ever eaten?
What type of dance routine would you do if you were dared to dance?
What is your favorite stupid joke?
If you had unlimited money, what is the first thing that you would do?
What is an activity that you have always wanted to try?
What household job do you hate the most?
If you could have magical power, what would it be?
If you could be a superhero, which one would you be?
What is one thing that you wish you could do faster?
If you could fly, where would be the first place that you’d go?
If you could have a car for free, what car would you pick?
If you could come up with an invention, what would you invent?
If you could improve one thing in your life, what would you improve?
What event from your past do you wish you could redo?
What event from your past do you wish you could relive?
If you were rich, how would you live?
If you won the lottery, what would you buy first?
What’s one thing that you can eat for the rest of your life if it’s your only option?
What is your favorite restaurant?
What is one country that you have never visited that you would love to visit?
If you could have three wishes, what would they be?
Do you prefer cats or dogs?
Do you prefer winter or summer?
Do you prefer the beach or a lake?
Do you prefer mountains or the beach?
Do you prefer to be hot or cold?
Do you prefer pizza or pasta?
What is it like to live your life?
What is one secret that you have never told anyone?
What makes you feel the most like your real self?
If you wrote a book what would the first chapter be called?
What would you title your book?
What actor/actress would you pick to play you in a movie of your life?
What makes you most emotional?
What is the last thing that made you cry?
What was the last movie you watched that made you cry?
What makes you happiest?
What people make you the happiest?
If you could be any celebrity for a day, who would you be?
What is the one thing that fascinates you?
What is an activity that you wish you could do?
What person makes you most uncomfortable?
What single word best describes you?
What do you hope to do with your life?
When you daydream, what do you think about?
What is your favorite animal?

What pet would you love to have the most?
Have you ever had a pet?
What is your favorite breed of dog?
What is the worst thing you have ever done that your parents know nothing about?
What is the most awkward thing that ever happened to you in school?
What is one decision that you would change if you could go back now?
If you could watch one part of your life, what part of your life would you choose?
What is one thing that you did and didn’t care about the possible consequences?
What is an event that changed your life positively?
What is an event that changed your life negatively?
Have you ever removed someone from your life?
What is your most favorite memory so far in your life?
How have you changed in the last five years?
What is the scariest thing that you have ever tried?
What is the most exciting thing that you have ever tried?
What is your favorite story to share with people?
What is your favorite holiday that you have ever been on?
What was your favorite television show as a child?
Who was your favorite celebrity as a child?
Who was your celebrity crush?
What is the most embarrassing thing that ever happened to you?
What is your most proud moment?
Who was your favorite musical band as a child?
Did you ever play a musical instrument?
Did you play sport as a child?
What was your favorite hobby as a child?
What is your favorite way to spend your Sunday morning?
What is your favorite way to spend a whole day with a partner?
What is your favorite thing about having a partner?
What is your least favorite thing about having a partner?
What is the most important lesson that you learned from your parents?
What makes a relationship healthy?
What is your favorite thing about being in a relationship?
What have you learned from past romantic relationships?
Do you prefer the city or the country?
What is the craziest thing that you have ever done?
How do you deal with having arguments with a loved one?
When did you realize you were in love?
What attracted you to me initially?
What did you think about me when we first met?
What is one habit that I do that annoys you?
What do you love most about me?
What can I do to make you happy?
What are your favorite things about our relationship?
What do you think about money?
What is a topic that you can never take seriously?
What is a lesson that you wish you had learned earlier?
What is the most important subject in school, in your opinion?
What is your favorite subject in school?
What is your least favorite subject in school?

what is your least favorite subject in school

What would be the most perfect day?
What do you like to do most?
What is your favorite thing to talk about?
Where is your favorite cafe?
Where is your favorite restaurant?
What is your favorite birthday present that you have ever received?
How would you most like to celebrate your birthday?
What is the worst birthday present that you have ever received?
Do you prefer your birthday or Christmas?
How do you and your family spend Christmas?
What is your favorite Christmas activity?
What is your favorite thing to do with your family?
Do you go on family holidays together?
Where is your favorite place that you have ever been with your family?
How are you similar to your parents?
How are you different from your parents?
What is the best thing that your parents have taught you?
Would you hope to have children?
What are your favorite baby names?
How many children would you hope to have?
Where would you love to live when you are older?
Where is your favorite place that you have ever lived?
What kind of house would you like to have when you are older?
What profession do you wish you could be in?
Do you have a university degree?
What is one subject that you wish you could study?
What is a lesson that you learned too late in life?
What is a lesson that you would teach your children?
What is something that you regret doing?
What is something you wish you had done earlier?
What are your plans for the future?
What have you always dreamt of doing?
Are you hard on yourself?
What are you hard on yourself about?
What standards do you hold yourself to?
What are the most important qualities in a person?
What do you value most in a partner?
What are you most passionate about?
What would you like to improve about yourself?
When have you felt the most tired?
Do you get stressed?
What is the most stressful thing that you have ever gone through?
Where would you live if you had unlimited money?
What is the last book that you read?
What is your favorite book?
What is your favorite film?
What can you cook the best?
What is your favorite takeaway food to order?
What is your pet peeve in relationships?
What habit do you have that annoys other people?

what habit do you have that annoys other people

What is an activity that makes you the most nervous?
What makes you most uncomfortable?
Do you mind talking in front of large groups of people?
What makes you the angriest?
When have you been the angriest?
What is a chore that you always avoid doing?
What is the saddest movie that you have ever watched?
What is something that you learned from a past relationship?
What is something that makes you jealous when you are in a relationship?
What do you expect from a partner in a relationship?
What is a habit that you have that is most unusual?
What is the weirdest habit that you have?
What is something that everyone overestimates about you?
What is something that people always underestimate about you?
How do you view yourself?
How do you think other people view you?
How do you want other people to view you?
What is your most controversial world view?
What is something that you will never do but you know that you should?
What is the most interesting conversation that you have ever had?
What was the best thing about your childhood?
What are you most looking forward to in the future?
What is your biggest weakness?
What is your biggest strength?
What was the biggest mistake that you ever made?
What is the best story that you have ever heard?
Where would you go on a road trip if you could go anywhere in the world?
What is the weirdest thing that you have ever eaten?
What do you do to calm down when you are stressed?
What is your favorite flavor of ice cream?
What animal would you most like to be?
Do you believe in astrology?
What is your favorite sport to play?
What is the weirdest thing that you have ever searched on the internet?
What is the weirdest phone call that you have ever received?
If you could change your name, what name would you choose?
What is your favorite song?
What is one song that you could listen to on repeat for the rest of your life?
What is something that you think should be illegal but is legal?
What is your favorite candle scent?
What is your biggest fear?
What is something that scares you the most?
What is the scariest dream that you have ever had?
What event in your life made you grow up the most?
What is the number one thing on your bucket list?
What makes you the happiest?
What is the luckiest thing that ever happened to you?
Would you change anything about yourself if you had the chance?
What is something that makes you interesting?
What is something you are really obsessed about?
What was your most painful experience?

FAQs

What are things to talk about with your boyfriend?

If you are wondering about things to talk about with your significant other consider conversation topics including asking him about the turning points in his life, the most painful call that he has ever received, or the most awkward moments of his life.

What are some good questions to ask your boyfriend?

If you are thinking of good questions to talk about with your boyfriend, consider conversation starters including what is his favorite thing to do, what does he value most in life, and what makes him most uncomfortable.

What questions to ask to keep a conversation going with a guy?

If you are looking for conversation topics or conversation starters to keep a conversation going with a guy, consider asking him about the things that he would never do, the best things about his childhood, and the things that he looks forward to the most in the future.

What is the game 21 Questions?

The game 21 questions include asking someone funny or personal questions to learn more about them. This is a great way to get to know your boyfriend better and to deepen the bond that you have in your relationship together.

How can I entertain my boyfriend over text?

If you want to entertain your boyfriend over text, consider playing 21 questions with him. Ask him about his favorite movie, the book that made him cry, or what makes him the most nervous.

To Sum Up…

Relationships can get boring at times and if you feel like you don’t know your boyfriend well enough, play 21 questions using the questions on this website to find out more about him. This is a perfect way to both have fun and learn more about one another and your relationship.

Let us know what you thought in the comments and don’t forget to share this article!

Do you hate it how everything seems to always revolve round him while you just seem to be an afterthought sometimes?
We hear this all the time from women that contact us asking for help with their relationship.

It almost makes you wonder whether he actually likes you or whether he's just stringing you along.

Why don't you take this quick free quiz to see if he actually likes you!

April Maccario

I'm a huge nerd when it comes to understanding how relationships between men and women work, and what drives a certain behavior. I spend much of my time getting into the nitty-gritty and try to share my findings on this site with the hope of making life a little easier for women that are struggling in their relationships or love life.