35+ Questions To Ask A Guy On Date Night

Updated April 2, 2023by Regain Editorial Team

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. You might not know each other too well, but you know 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 might be a good way to prepare.

Knowing what questions to ask a guy on a date can ease your nerves. It could also help spark new conversations and keep existing conversations going, which tends to be a goal on dates. Talking about various topics can be an effective way to determine compatibility, too. 

How To Choose The Right Questions

How’s The Communication In Your Relationship?

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 questions to start. There may be endless questions you can ask a guy during a date.

With all these options, you might wonder how to choose questions to ask. It could be helpful to keep in mind that the questions you ask should be suitable for the length of time you’ve known the person. You might ask a question related to something you already know about your date, for instance, such as how they got into their line of work.  

From fun questions and  philosophical questions to more targeted questions that will help you learn more about their interests, hobbies, or future ambitions, you can make your date night a remarkable one.  

Questions For The First Date

If this is the first date, you might want to start with a friendly question. You may want to learn the basics about this person, but you might not want to ask something too personal within the first few minutes of seeing each other. You could start with an open-ended and straightforward question such as:

  • Where did you grow up?

  • What’s something your hometown 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 could throw in some interesting questions like:

  • 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 and ask him some deeper or more personal questions. Some deep questions might include some of the following:

  • 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

Perhaps 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. 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 not want to build feelings for someone whose ideas and values on raising a family are far too different from yours. Thus, you might also ask some questions about family life. For example, if they’re set on having kids, and you don’t want them, that may be an essential base to cover. If you’re at this point in the relationship, you might consider asking a 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 your family?

  • What 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?

Consider selecting serious questions that fit your comfort level and theirs. If things start to feel tense, you might want to break it up with some light-hearted questions to keep things casual and fun.

Pop Culture Questions

On your date, you may want to find some light-hearted common ground. Consider asking some movie-related questions.  Questions like these can help you connect on a playful level:

  • 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 might be a good idea, too. For instance, you could ask your date if he remembers a throwback hit or inquire about his favorite bands and artists.

Questions To Spice Things Up

How’s The Communication In Your Relationship?

Depending on what your connection is like, you might want to ask some flirty questions. These questions don’t have to be sexual or related to sex, but they can be as long as you’re both comfortable with this type of banter.

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 ever had?

  • How come a handsome guy like you is 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 can be important for the relationship’s growth. Still, it’s best to gauge your partner’s comfort level (or even ask directly), and be respectful.

Listening Matters, Too

A good date may be more than just asking the right questions. Consider flexing your capacity to listen as well. You might not want to get caught in a moment of distraction or have to ask the guy to repeat himself because you were not listening. Though some may forget, listening is arguably one of the most vital conversation skills.

Consider 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. If you’ve considered counseling in the past but have been hesitant to reach out for professional help, you’re not alone. Many people shy away from speaking to a stranger about issues surrounding romance, especially in a clinical setting like a therapist’s office. Online counseling may be a solution that puts you more at ease while getting the help you need to successfully navigate dating and relationships. Internet-based therapy can also be more convenient since you can access it from home or anywhere you have an internet connection.

This type of therapy is also versatile and effective. A comprehensive meta-analysis in the field of mental health and psychotherapy probed almost 10,000 individual cases comparing in-person and online counseling and found no significant differences regarding outcomes. The review included various populations spanning a wide range of mental health challenges and conditions. 


Dating can be challenging. Not only is it hard to find the right person, but you may also have to face rejection, love bombing, and the dreaded awkward silences. Regain is here to help, though. No matter the dating or relationship issue, we have an experienced counselor you can talk things through with. Reach out today, and start dating purposefully. 

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