Good Questions To Ask A Guy On A Date Night

Updated July 07, 2020

Medically Reviewed By: Amy Brown

It’s a Friday night, and you have a date with the guy who has been asking you out for some time now. You have finally decided to give him a chance, and while preparing, you are contemplating what kinds of questions to ask him. He looks promising with a great career, and you certainly do not want to mess this up. What do you want from this date? It’s a great question to ask yourself. The good question, however, should be how you want the date to end.

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The truth is, the first dates are tricky, and you want to make a good impression. Depending on what level you both are on, you can come up with a friend zone, love questions, simple questions, or even flirty questions as these questions will help you to know a lot about the guy. While it is not much of a fuss to ask random questions and noting that first date questions can vary from individual to individual, the choices are, however, endless. The kind of questions you should ask do not necessarily have to be the same ones you asked the last guy you were on a date with. There are tons of interesting questions you can ask during this date. From fun questions, philosophical questions, to some great questions that will help you know more about his interests, hobbies, or future ambitions- you can make your date night a remarkable one.

One thing you are hoping to achieve during the date is to get to know the guy better, while also having a good time. Of course, if you are looking forward to going on more dates with this guy, you would probably want things to go well. You must ensure you ask your questions with caution. As you prepare for your date and come up with a list of questions you plan on asking, also note that it is essential to allow the conversation to flow naturally and give your guy the time to answer at his pace.

You most definitely do not want to have forced conversations, so you should draw up a list of some interesting questions to use for the night. You can also talk to your trusted friends- mainly guys- to give you good ideas on what questions to ask your date. You might just get a better insight into what it takes to talk to a guy and some good questions to ask.

Remember what they say about first impressions? You should be careful not to look desperate or too inquisitive. Of course, it is not compulsory that you must exhaust the questions on this list- it is a date, not a job interview. It is also advisable to keep the philosophical questions at the back burner, except for when the opportunity arises, and there’s a need to throw them in.

You both are still friends, and it is only a date to help you know each other better, so you can  start with an open-ended and straight forward question such as;

  • Where did you grow up?
  • What is your favorite food?
  • What is your definition of a perfect weekend?
  • What do you do to have fun?
  • What do you consider an interesting part of your work?

At this point, you may want to switch the mood up a little with some fun, lighthearted questions to keep the fun going. You can throw in some interesting questions like:

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  • What has been the best or most memorable day of your life so far?
  • What was your most embarrassing moment in high school?
  • What is that one thing you have been too scared to try out?
  • If you had a chance to be President for one day, what would you do first?

If you want to appear kind of unpredictable and spontaneous, you may go ahead to ask him some deep questions. One thing you should be wary of, however, is appearing desperate, so you should ask these deep questions in a way that they seem like follow up questions to the conversation already ongoing. Some deep questions which would seem like a sequel to the last light-hearted question could be some of the following;

  • What would be your approach to resource management if you become the President of the country?
  • What is your take on domestic violence in relationships?
  • Would you have a joint account with your spouse?
  • What is your opinion on divorce?
  • What is your understanding of raising children?

At this point, you may want to consider allowing him also to ask some questions he may have had in mind for you as well, while you think up on more follow up questions. There is a good chance that his own questions can lead to other additional questions for you. So at this point, taking a back seat and allowing him to take over the questioning would be a good idea.

Regardless of the kinds of questions, he may ask, your focus on your follow up questions should remain intact. However, be intentional and creative; try as much as possible not to ask endless follow-up questions.

Also, note and avoid some weird questions that can throw him off balance. Your follow up questions should spice the mood up and not drain it. Be intentional; you can even refer to something he may have mentioned lightly while talking; this gives you credence and shows that you were paying attention while he was talking or asking his questions. So he asks this fun question which he imagines you will answer excitedly, a good question but it not been answered because you were not listening.

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A vital element to hold in place during your conversation is your ability to listen. You do not want him to feel you were absent-minded when he asks a question, and you tell him to please repeat it because you were not listening. Many people usually forget that listening is a massive ingredient of conversations. You will come off as tacky and uninteresting if you find it challenging to pay maximum attention during conversations, especially on a first date.

At this point, you can throw some in some fun questions that are movie-related. You would discover it’s a fun question, and in fact, the question is great because he would most likely be in high spirits to discuss his favorite movie, especially if you are on the opposing end. Great questions like these can help you lighten up the place:

  • What is your definition of a good movie?
  • What would you make of HBO’s Game of Thrones’ final season?
  • If you were to play a role in a movie, which would you prefer to be – the good guy or bad guy?
  • Which movie character can you relate with?

The sole intention for this date is so that it leads to even more dates in the nearest future. These questions will help you understand the guy’s ideologies, fun ideas, and mentality about relationships. Do not attempt to fan embers of sarcasm, especially if you observe that he may not be the type that will entertain or understand sarcasm and may not find fun questions or funny questions all that funny. Hence, ask your questions with caution, so the date does not end abruptly if he finds any funny question, offensive. You do not want him to go silent on you through the period of the date. Imagine asking a great question that is supposed to be exciting, and then he just gives a disinterested nod as a response.

Also, avoid asking personal questions, especially if he dodged discussions in that line once or twice during the conversion. There is a good chance that questions like that are not the best questions to ask, as they probably trigger old memories.

There are questions for finding out his opinion regarding sex. In the course of the conversation, try to recall phone or chat conversations you may have had with him before this date. If you consider him the type, you can throw in a flirty attempt by asking some truth or dare questions.

Some flirty questions you can ask are:

  • Is kissing on the first date a good or bad idea?
  • When and where was the best kiss you had?
  • How come you are still single?
  • How long was your last sex session?
  • What is your sexual fantasy?

Do not lose foresight of the fact that you are still in the friend zone, though this may change depending on how well the date turns out.

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One thing you should also remember is that it is alright not to have all the answers. Having an opinion does not necessarily mean having an answer. You may ask a question, and he responds with nothing concrete. You need to understand that the way girls and guys think and react to situations differently, so try as much as possible not to take offense.

Furthermore, you can also try to figure out his family values by asking great questions about his current family life and his values regarding family. One thing you want to find out during this first date is if he has core family values that resonate with you, as this will help you determine if you both are on the same page and if there is a chance of building a future together. You do not want to build feelings for someone whose ideas and values on raising a family is different from yours. Asking him these important questions sets you up with the right information if at all, you both proceed beyond the dating level. At this point, you can throw in a great question to find out if your family values align. Examples of such questions include;

  • What is your picture of an ideal family?
  • Who are you close to in the family?
  • How was growing up with your siblings like?
  • Which parent do you take after in terms of character traits?

While keeping tabs on the fact that you want to get to know him better by asking the important questions, you should also be aware that he probably came to the date as prepared as you are and armed with questions to find out as much as he can about you. Therefore, you should allow the fraternization to be as natural as possible, while you build a good conversation with him.

There is a possibility that you both have had a great time at this point, chatting away and laughing your hearts out. The issue of compatibility is, therefore, going to be considered either during or after the date. The question on your mind at this moment, which is a good one, would be whether or not you want to meet him again.

Knowing that conversations are possible without a physical meeting, a date is more than just a question and answers session. As much as you both are having fun while at it, you should ensure you read the unsaid reactions and words that he may not be saying verbally—his facial expression and other body languages.

The list of fun questions for first dates is non-exhaustive, depending on how much information you plan to get at the end of the date. Also, remember that these supposedly great questions vary from person to person. However, the primary focus should be having a good time while getting to know him. You don’t want to mess up a potential relationship before it even got to start. This data can help you gain a good knowledge of the guy’s perception about relationships and help you understand men better.

Need professional advice on how to grow friendship into a relationship, recognize time wasters, or strengthen your current relationship? Then you should talk to certified relationship counselors and licensed therapists like those at ReGain to get the help you need.


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