How to Play the 20 Questions Game with Your Partner

Spice Up Your Relationship with the 20 Questions Game

By Fred S.
How to Play the 20 Questions Game with Your Partner

One of the best-known and oft-enjoyed parlor games has come a long way since its popularity as a renowned TV and radio show that had most of our ancestors hooked for a great couple hours. 

The 20 questions game has proven to be an excellent means of getting to know your partner better, or if you are still hiding your feelings from that one friend you have a relentless crush on, this little exercise can help you see if all your efforts are really worth it. 

It can be played without any pens, boards and vast playgrounds; you can merely be cuddling up with your boo while watching your favorite show and start asking them 20 questions that have to be replied with a one-word answer, preferably a yes or a no. 

Where Did This 20 Questions Game Idea Come from?

Each country has a varying history as to when this game actually came into being. In America, it is thought to have been a product of sheer boredom in the latter half of a diplomatic meeting. Sounds strange, but it is factually correct as it was in the memoirs of the US ambassador to Great Britain that were a recollection of his time in the capital in 1823 when the then Secretary of State for Foreign Affairs of Britain suggested a round of 20 questions to rid a group of people of their vapidity.  (source:

This later was to form the basis of the best means to pass time that you would have otherwise spent in vain and also gave many channels back-in-the-day the recognition for their entertainment they yearned for.  

20 Questions Game to Ask a Girl

1. Do you prefer your natural skin or makeup?

This question can help her get more comfortable around you. An added benefit of the answer could be a later fruitful discussion of self-esteem issues that you could help her with and make her like you ever more.  

2. Name your favorite eating spot?

A single answer to this query and you would never have to spend a long time deciding where to eat ever again.  

3. Have you ever used a fake ID?

 A straightforward question with a yes or no answer that could lead to your partner sharing the best story from their younger years with you, birthing multiple intimate laughter sessions.  

4. Would you rather have a dog or a cat?

Everyone loves fluffy animals. Knowing whether your girl is a dog person or a cat person can help you tailor your presents for all the occasions to come and probably help you with envisioning a future home together in a better way. 

5. Would you rather be rich or intelligent?

Answers like these are usually very deep and have a backstory, plus a one-word answer. This can help you two know each other better than ever if you bring this up again, but after the game ends. No elaborate reasons while playing! 

Related Article: 10 Things You Should Do If You Love Someone So Much
10 Things You Should Do If You Love Someone So Much  The butterflies in your stomach are not you being hungry or you feeling sick but are in fact knots in your stomach hinting that this person..

6. Which one is your favorite Pokémon?

Major points to your partner if there is a Pokémon she loves, but no problems even if she doesn’t. 

7. What is your favorite zodiac sign?

Proceed with caution; this one might hurt if it isn’t yours. 

8. Who is your favorite singer?

Grow stronger by having matching playlists and surprise her with gig tickets. 

9. If you had the chance to go to a pool party with a celebrity who would it be?

Control that envy and get the coolest replies. 

10. Which one’s better: black coffee or a tall cup of creamy latte?

The foolproof way to have someone’s heart and to keep it is to bring them their beverage as they like it. 

11. Would you rather choose unlimited sleep or unlimited money?

The answer to this one word question would just reveal your baby girl’s priorities in life. 

12. Have you ever made a fake account to stalk someone?

A simple yes or no would suffice to make you realize that your partner would have had a successful career in the FBI. 

13. Who would you rather grow up to be; your mother or your father?

This answer would help you assess whose traits your partner is more appreciative of and let you learn about them in a better light. 

14. Pajamas or skirts?

Some girls don’t really care about anything but their comfort, while other would compromise their own ease for fashion, this question will tell you which category your beloved belongs to.  

15. Which ones taste better, fries or tacos?

Short on cash? The next time you have a date night on a budget, you’d know where to land. 

16. Would you rather get hurt by knowing the truth or love to be oblivious for the sake of peace?

This is a philosophical scenario that would reveal to you a lot about your partner. 

17. Black or white?

Update your wardrobe after this. 

18. What do you love receiving, chocolates or roses?

Well, we still prefer that you bring both, but her opinion matters more. 

19. Would you rather exist in Twilight or Harry Potter?

Explore the nerd side of your darling. 

20. Do you think you are good in bed?

End it with a question that is both intimidating and sensual, who knows what might follow?  

20 Questions Game to Ask a Guy

1. In a game of truth or dare, which one would you opt for?

Spin the bottle right next time and know what to do with your boo. 

2. Would you rather have superpowers or an unending life?

This might be a hard one for your baby boy, but there is no harm in putting it out there. 

3. Do you love kids?

Add points to his already cute personality and know what to expect if you ever tie the knot! 

4. Would you ever sign up for a risky space travel?

Is your boy as curious about the universe and its untold tales as you are? This one will help you find out.  

5. Where would you get your first/next tattoo?

The answer could help you know what you should get him for his next birthday. 

6. Cars or bikes?

Learn whether your guy is a fan of driving or riding while playing a fun game. 

7. Would you prefer reading the book or watching the movie?

It is always better to know beforehand if your partner is a reader or a viewer, solves a lot of puzzles you know.  

8. On a scale of 1 to 10, how much would you rate yourself as a kisser?

It might be time to make some amends after the answer to this one. 

9. Marriage or relationship?

This one might shake things up a bit, but also allow you two to manage the direction of your partnership in a better fashion.  

10. Do you prefer making out with the lights on or lights off?

This is of utmost importance! Ask away! 

11. Texting or calling?

Let’s sort this out for once and for all. Also, helps you plan your days away better. 

12. Which emoji do you think represents my personality the best?

Let them show this on their phone and have a good laugh.  

13. Would you move to the North Pole just to be with the penguins, but the cost is living there all alone?

This should help you judge your love’s love for fluffy penguins! 

14. Pineapples on pizza?

This should lead to a very abrupt response with a hilarious expression, we bet! 

15. Have you ever been in a physical fight during your high school?

Relive an adrenaline-powered story with your beau.  

16. Have you ever got caught cheating on a test?

Yikes! An honest answer to this would represent how naïve your baby boy is. 

17. Have you ever stolen your parents’ money?

Comic books, illegal booze, party or even night out a bar, what could your partner have possibly done? Keep the story for a later time if the answer is a yes. 

18. Have you ever had a sexy dream about me?

Wet dreams are not a secret, but how good does it feel when you are the reason why your guy is having them?! 

19. Late night cruise or a stroll?

The choice would help you with all your future date nights.  

20. Is there anything in me you would want to change?

For most people, the answer is a simple smooch on the cheek or an affectionate embrace. Ask to find out which one is it for you! 

Rules of the 20 Questions Game

  • The number of questions should not exceed 20, it could turn insipid otherwise. 

  • Keep the questions real and pertinent to your relationship. 

  • The answers should preferably consist of one word. 

  • If you are aware of a traumatic experience your partner might have went through, make sure that you do not ask anything that might bring back the pain. 

  • Do not ask questions you would not like the answers to. 

  • The questioner cannot help the answerer in anyway, if the former is unsure of the answer, they need to reply with “I don’t know” without giving away the solution. 


Getting to know each other better and adjusting to what you learn in this manner is the best way to enjoy a healthy relationship. Occasionally engaging in the 20 questions, when the time and mood are right, is a joyous way of delving deeper into the person who you share a bond with, minus all the boring seriousness that is endured if they were asked in any other way. 

So, the next time you two are just idling on the couch and have nothing else to do, initiate this old-fashioned parlor game and keep taking turns to learn things about one another that are both funny and philosophical.   

Related Article: What Does Love Feel Like Physically And Scientifically
What Does Love Feel Like Physically And Scientifically Love is a powerful, life-changing and complex feeling that we all experience at some point in our life.