Good Questions To Ask A Guy On A Date Night

Updated October 25, 2021

Medically Reviewed By: Amy Brown

Getting ready for a date can come with some nerves, especially if it’s with someone who has you particularly smitten. Maybe, it’s the first date, and you don’t know each other all too well, but you know that they’re cute and you’re interested. Perhaps, you’re a few dates in and want to know what questions to ask to see if this connection is worth continuing or not. Either way, having some questions on hand to ask someone on a date night is a great way to prepare.

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Knowing what questions to ask on a date can ease your nerves and help you relieve or mitigate any potential awkward silences. Questions, after all, spark new conversations and keep existing conversations going, which tends to be a goal on dates. Talking about various topics, after all, is how you’ll know if you click. Alternatively, how you’ll know if you don’t. So, what are some good questions to keep in mind?

How To Choose The Right Questions

Depending on how much you’ve spoken already, the questions you ask might fit into different categories. You can come up with friendly questions, simple get-to-know-you questions, deeper love and romance-related questions, flirty questions, or quirky, silly questions to start. In other words, there are tons of thoughtful questions you can ask during this date.

How do you know which ones you should use? Of course, the questions you ask should be suitable for the length of time you’ve known the person, and they should also feel like relatively natural questions to ask. You might ask a question related to something you already know about your date, such as how they got into their line of work if you know a little bit about their career but don’t know the details, or pick a question that serves as more of an icebreaker.

From fun questions, philosophical questions to some great questions that will help you know more about their interests, hobbies, or future ambitions - you can make your date night a remarkable one and gauge whether this is someone you get along and are compatible with.

Questions For Date #1

If this is the first date, you probably want to start with a friendly question. You want to learn the basics about this person, but you don’t want to share information that could compromise your safety or ask something too personal within the first few minutes of seeing each other.

You can start with an open-ended and straightforward question such as:

  • Where did you grow up?
  • What’s something your hometown (or home state, province, etc., depending on geographical location) is known for?
  • 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 unique asks. 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?
  • What was your college experience like?

If you want to appear unpredictable and spontaneous, you may go ahead to ask him some deeper or more personal questions. 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’s an experience that shaped who you are today?
  • Is there anything you’d do or change in your life if it weren’t for what other people might think?
  • If you were given a chance to give a speech about anything, what would it be about?
  • If you weren’t in your current occupation, what do you think you’d be doing? What would you want to do?
  • Do you prefer city life or small-town life?

Questions That Cover The Serious Stuff

Let’s say that you’re at a place with this person where you want to get down to business and learn if you’d work out long-term. That doesn’t mean that you want to rush into things. Instead, it’s that you don’t want to waste each other’s time. When you’re ready, here are some questions you might ask:

  • How would you personally describe your political beliefs?
  • What are your deal breakers in a relationship?
  • What are you looking for in a partner and relationship?
  • How do you balance interdependence and independence in relationships?
  • What are your thoughts on marriage?
  • Would you have a joint account with your spouse?

You might also ask some questions about family life. You do not want to build feelings for someone whose ideas and values on raising a family are far too different from yours. For example, if they’re set on having kids, and you don’t want them, that’s an essential base to cover. Differences in a partnership can be a great thing, but some things might be a no-go. Asking your date 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?

What is your understanding of raising children?

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Make sure to go with serious questions that fit your comfort level and theirs. When the time feels right, don’t hesitate to break it up with some light-hearted questions to keep things casual and fun.

Pop Culture Questions

Want to find some light-hearted common ground? At this point, you can throw in some exciting questions that are movie-related. You would discover it’s a fun question, and in fact, the question is great because they would most likely be in high spirits to discuss their favorite movie, especially if you are on the opposing end. Amazing 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, would you prefer to be – the good or bad guy?
  • Which movie character can you relate to?
  • If you were an animated character, who would you be?
  • What was one of your favorite movies as a kid?

Questions that help you learn about a person’s music taste are a great idea, too! This could mean anything from asking if they remember a throwback hit or asking their favorite bands and artists.

Questions To Spice Things Up

Depending on what your connection is like, you might want to ask some flirty questions or sexy questions. Flirty doesn’t have to mean sexual or related to sex, but they can if that’s where you’re both at, and you have consent.

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?
  • What is your sexual fantasy?

You can also ask flirty “truth or dare” questions. Only ask questions related to sex if it feels appropriate for the connection you have. Communicating about sex is extremely important because you need to know what each other like to have a good sex life. Still, it’s non-negotiable that this occurs when it is reasonable and respectful to ask.

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Listening Matters, Too

It’s not just about asking the right questions. A vital element to hold in place during your conversation is your capacity to listen. You do not want them to feel you were absent-minded when they ask a question, and you tell them to repeat it because you were not listening. Of course, this will happen from time to time if you don’t hear what they say, but overall, listening matters. Though some forget, listening is, in fact, one of the most vital conversation skills, and it’s most certainly part of being a good date!

If your date seems uncomfortable with a question you ask at any time, it’s best not to press them. Especially if it’s a first or second date, remember that you also don’t have to share anything that crosses a personal boundary or that could be risky to share at this point in getting to know somebody. The ability to set boundaries and respect boundaries are both great signs and skills, and as your comfort grows, you can share more.

Find Counseling

Whether you’re dipping your toes into dating, are in an ongoing partnership, or need help with something else that’s going on in life, counseling can help. You can get support from a counselor in person or use an online counseling platform. ReGain offers both individual counseling and counseling for couples, and all of the providers on the platform are licensed. Healthy relationships matter, romantic and platonic, so don’t be afraid to take the first step toward finding a professional to talk to today.


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