Top 15 Interesting Questions to Ask a Guy on First Date

Well, we all know how special first dates are. They come with an overflow of adrenaline rush inside of us, shivers going down the spine and the classic butterflies in the stomach. Amidst all this, comes the bigger picture. WHAT TO TALK ABOUT? HOW TO KEEP THE CONVERSATION INTERESTING?

You are meeting a guy for the first time; you obviously have no clue as to what his likes and dislikes are. What does he do, what interests him and what doesn’t. And that is not it, you by all means wish to make that first impression so good that it lasts long and makes him ask you out for a second date. It’s natural that you’ll ponder upon the conversation starters. You would tremble and it may get awkward.

To rescue you from the awkward ‘what to say next phase’ following are the best questions that you can ask and indulge in an interesting conversation.

 1.    What is something you want to try in your life?

Ask him about the things he wishes to try in his life. Make yourself aware of all the things he would love to do and wants to do. This will give you an insight onto his adventurous side, if he has any. This would be a great conversation starter; he’ll think that you are interested in knowing things about him.


 2.    Which fictional character can you relate yourself with?

This question may seem a little too intellectual or interrogative but this would actually give you a fine picture of what he thinks of himself or how sees himself. The character he tells you would have the qualities he possesses, so it would be much easier for you to make out his likes, dislikes and personality.


 3.     What’s something you are not so good at?

Let’s skip the monotonous question ‘what are you good at or what do you do the best’ and ask this thing straight. Well, it may come off as too bold but you can always make it light hearted by telling your own example like you can say I am terrible at cooking, what is something you wish you could do better? This will help you know his flaws. Also, this will show how much he knows himself and wishes to work upon himself.

4.    What’s your goal in life right now?

Ask him about his goals, his targets and his desires. You’ll know how career oriented he is, how much he takes his life seriously and wishes to accomplish something.

5.    What do you hate about dating?

Well, this is an important question for obvious reasons. You most definitely should ask him this. His answer would help you avoid things which he considers as a turn off and would help you to do things which he wants a girl to do for him. Also, this question will give you a hint to what’s going to happen after the date, how you guys would take things forward.

6.    If you could possess one superpower, what would it be?

This is something which we all would love to answer. It’s not related to dating but it is an interesting question to put forward. It would make him take off his mind from all the dating stuff. He would love to answer this and would consider you interesting and good to talk with.

7.    Which is your favorite book?

A guy who loves to read is a cherry on top isn’t it? Yes it is. I would personally like a guy who is intellectual and reads good books. A person who reads is knowledgeable. And who knows his favourite book might be your favourite too. How great would that be? You’ll have so much to discuss upon.


8.    Do you know how to cook?

One of the traits we all wish guys possessed. Cooking involves patience and calmness. If he loves to cook, you would know you are with a guy who is patient. Also, a guy who can cook great meals for you while you lay off in laziness would be the loveliest thing to ever happen.


 9.    Do you have any Tattoos?

Ask him if he has any tattoos, this would be an interesting conversation starter if he has any. The sort of tattoo he has will tell you a lot about his personality. Tattoos symbolise courage and commitment. If he has a tattoo, he is ready for a commitment because tattoos stay lifelong. Guys who can guarantee commitments are desirable.

10.     What’s your horoscope sign?

This may seem an old school question but it can be a great test for compatibility. Knowing his horoscope would help you a lot in knowing if you both are compatible with each other or not, whether he has a temper or is an easy going person. A lot can be derived from horoscope signs.

11.  What do you do to relax yourself?

Relaxing oneself can involve a lot of things like going on a walk, taking a spa session etc. If he says drugs or alcohol, you must walk away that time itself. Nobody wants a guy who is addicted to substance. It’s a major turn off.

 12. When was your first kiss?

Well if you wish to make the conversation a bit flirtatious, you should go for this question. Break the interviewing session into a lighter conversation. This question will set the mood right for your date. After all healthy flirting never killed anyone.

13. Have you ever cried while watching a movie?

This is an interesting question to ask in order to know if he has a sensitive side. If he replies in affirmative, you’ll be aware that he is opening up to you and is letting you witness his tender side.

14.What are a few things on your bucket list?

Everyone has a bucket list. Something we want to do or accomplish. Let him tell you about the things he has on his bucket list. If things which he has on his bucket list matches with yours, you both can dream of how to accomplish them. Also, you may get fascinated by the things he has on his list, and you could totally add it onto yours.

15.Who is your celebrity crush?

It may seem a little pointless but actually it is very advantageous. The name of the celebrity he replies would be the type of girl he feels attracted to. The type of girl he admires and wishes to be with. This will help you know his choice in women. Isn’t it cool, to ask a question in an indirect manner that you were dying to ask but thought you’d look desperate.



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Nikita Dhingra

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