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21 Questions Game: First Date Edition

Updated on February 25, 2015
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My name is Tatiana, but my family & friends call me Tutta. I love spending time with them, and hope my writing brings more people together!

There’s nothing quite like the honeymoon stage of a relationship; you know, the very beginning where everything seems like magic and you just can’t seem to get enough of the other person! It’s a crucial state in any new relationship as you both learn everything there is to know about one another, or so you think you are learning everything!

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21 Questions Game

Asking a multitude of questions is perhaps the fastest and easiest way to get to know that someone special you are seeing!

The 21 questions game can really facilitate the “getting to know you” process while making it fun! Literally, it’s simple: You get to ask any 21 questions your heart desires! It’s best to make the 21 questions game fun, though, while throwing in a few more serious questions into the mix.

Here are some examples:

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  1. If you were a dog, what kind would you be? This is a good one because different breeds of dogs are associated with different behaviors and personality traits. For example, chihuahuas are known to be shy, timid, but snap when needed, pitbulls have a rep for being strong but aggressive, and poodles are viewed as prim, proper, and sometimes a ‘stuck up’ kind of dog.

  2. What is your ideal first date? Asking this question, you can get an idea about how frugal or simple he is, which is a good thing if that’s what you’re looking for in a guy! You can also learn what his intentions may be, for example, if he mentions a kiss or even sex after a first date.

  3. Do you like to dance, and if so, what kind of music? Perfect for a first date where music is being played, because if there is a DJ around, you can get your man on his feet to see what kind of moves he has!

  4. What kind of vacation would you prefer to take? It’s pretty important to enjoy the same type of vacations since you will be doing them together, so whether it’s a beach resort, a cruise, camping, or exploring the earth’s wonders, see if you have it in common!

  5. If you were stranded on an island, what three things would you be wishing you had? Assess his survival skills, priorities, and his ability to view a problem situation with clarity.

  6. What is your biggest long-term goal? Everyone should have things that are important to them that they have to work towards in life.

  7. What is one thing that always makes you laugh? The ketchup fart noise? Oh, me too.

  8. Do you believe more in saving, investing, or taking chance in gambling? Knowing how they handle their finances ahead of time is definitely a plus!

  9. On a scale of 1 to 10, 1 being dirtiest, and 10 being cleanest, if I were to go to your house right now, what would it be? Be easy on him, we all have our flaws!

  10. If you had to choose, would you choose a girl who’s dumb and gorgeous or smart and ugly? In other words, is he vain or an intellectual?

  11. What is your favorite thing to eat for breakfast? This will give you a good idea on how healthy he eats in general. Does he start his day with processed sugar and coffee or a glass of OJ and a plate of protein?

  12. Do you have a favorite childhood memory? Sure he does! Let him feel nostalgic a bit during this game of extreme questioning!

  13. What is the most daring thing you have ever done? How much of a wild side does he really have?

  14. Are you more of a cat person, a dog person, or a reptile/amphibian person and why? People often gravitate towards the same qualities in animals as they do in humans, minus a bunch of fur or scales, of course!

  15. What is your favorite TV show? Does he enjoy low brow comedies or shows that require a bit of brains to understand? Perhaps something in between?

  16. Can you recall a time you were dishonest? If he says no, then he’s being dishonest!

  17. Have you ever been in trouble with the law? This is definitely a good thing to know ahead of time, and another way to test the honesty of the potential partner! If they are willing to fess up about a crime committed (depending on severity), then maybe they’re honest enough to be given a chance. No trouble is better!

  18. What size shoe do you wear? You know what they say about a guy with big shoes, right? Big feet.

  19. Have you ever been to the hospital? For what? This can sometimes yield the most entertaining answers, so don’t be afraid to ask him to elaborate if he is shying away from the question!

  20. What is your everyday apparel like? An excellent way of asking if they are a slob or care about their general appearance, which is important to an extent.

  21. What’s the most embarrassing thing that has ever happened to you? We all have had some pretty embarrassing moments, and being able to communicate about them shows character and how you are able to grow and overcome sticky situations!

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Getting to Know You

Choose your questions wisely, make it fun, and most of all, smile at the fact that you are ceasing the opportunity to really get to know each other on a whole new level!

Although it will never be possible to get to know someone completely from a single game, that’s a part of the beauty of relationships, that you are constantly learning about who they are!

24 Questions You Should Actually Ask On A First Date

Are you going to play the 21 Questions Game on your next date?

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