Fun, Sweet, Naughty, and Witty Dating Questions to Ask a Girl


Wondering how to get the date started? Here are some interesting questions to ask a girl to get to know her more, and create good opportunities to improve on the conversation.

Did You Know?

That men know they are falling in love much sooner than women do. On an average, while men start falling in love around date number 4, women take almost 4 times as long (that’s date 16!) to fall in love!

The purpose of dating is to get to know someone better. And so it follows that you have to ask someone questions about themselves, to get the conversation going, as well as to get them talking. It is really important that you ask the right questions at the right time, since inappropriately timed questions can hamper your chances of winning another date.

Listed below are some questions that get you going, but it is up to you to figure out the right time to ask them. The trick is to discover the other person slowly, to keep the interest sustained. So avoid making the first date a marathon question and answer session! Instead, spread them out over a few dates, starting off with the really casual questions on the first date, and then making them more personal or intimate. Try to keep the questions to a reasonable amount, say maybe 5 to 6 questions per date. What you have to realize is that asking questions is not the only way to get to know someone. Starting random conversations and getting the other person to open up is a skill, which you will have to acquire, or polish! In the meantime, here is something to get you started…

Interesting Dating Questions

couple on date

– Do you believe in making compromises for a relationship/marriage, and to what extent?
– Do you believe in God and Ghosts?
– Do you believe in soulmates?
– What are the 5 things you can’t live without?
– What’s your biggest fear, and your biggest strength?
– Name 5 people you cannot do without?

– Which is the most beautiful place you’ve ever seen?
– Do you believe in love at first sight?
– Are you scared of opening up to people? If so, why?
– What qualities would you look for in your partner?
– Does your first love still hold a special place in your heart? Who was the lucky guy and are you still in touch with him?
– Do you forgive easily or forget easily or both?

couple on date

– If you get to be someone else for a day, who would you want to be?
– How many children do you want to have, and when do you want to have them?
– If you had to choose to live with someone who truly loves you, but you don’t love him back, or to live alone for the rest of your life loving someone who doesn’t love you, who would you choose?
– If you could time travel, which era/year would you want to go to? Why?
– What, according to you, are the three most important things in a relationship?

– How do you spend your weekends/days off?
– Do you like animals?
– What are your hobbies?
– Would you like to change your surname after marriage or stick to your maiden name?
– What genres do you prefer in – movies, music and books?
– Which are some of your favorite books, songs, and movies?
– Which is your favorite cuisine/restaurant?

couple on date

– Which was your best vacation to date?
– Do you have siblings? Are you close to them?
– Who knows all your secrets – mom or dad?
– Do you have a wish list? Can you share some of the things on it with me?
– Would you bungee jump/get a tattoo on a dare/whim?
– If you had a million dollars, what would you do with the money?

– If your partner wants to do something you don’t particularly like/enjoy, would you do it with him?
– Are you open to experimentation in the bedroom?
– What are your future plans?
– What’s your idea of fun?
– An ideal evening would be spent alone or with friends?
– Which, according to you, is the most romantic musical instrument/language?

couple on date

– Which was the best date you have been on?
– Arrange according to preference – sun, sand, snow?
– Do you like going to the theater or for concerts?
– Which is your favorite sport? Do you follow it or play it?
– What are your thoughts about marriage and religion?
– Do you like to travel?

– Is there any goal/dream you have which you think cannot be fulfilled now because it’s too late?
– Which is the one place you would like to visit/settle in?
– Have you done something special for someone without their knowledge?
– Have you/would you drop everything at a moment’s notice if someone you cared about needed your help?
– Can you tell me about an incident in your life that is close to your heart?
– What turns you on?

couple on date

– What are your main inspirations in life?
– What do you do to cheer yourself up if you have had a bad day?
– What’s the one thing you have done that you regret?
– Are you a morning person or a night person?
– What are your ambitions and pet peeves?
– If you could be in a movie, which one would you want to be in, as which character, and why?

– Tell me one thing that you have done/accomplished, that makes you proud of yourself?
– What’s the best free advice you have been given?
– Which was the best/most stimulating conversation you have ever had? Whom did you have it with and what was it about?
– What is your wildest fantasy and who is in it?
– Which is the cutest/funniest/sweetest/weirdest compliment you have received?
– Would you expect forgiveness if you cheated on your partner? Would you forgive your partner if he cheated on you?

There you go! Some questions are meant to know whether you are compatible, some are meant to make her laugh, some are questions to ask a girl on a first date and some are meant to convey subtle signs of vested interests! These questions need to be asked at the right time judging the mood of the moment. Go on and get to know the girl. She may just turn out to be the one!

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