First Date Questions? We’ve Got You Covered!

It’s taken some courage to approach someone and ask on a first date. Now you’ve done it, and you are facing the nerve-wracking issue of how that first date conversation will go. How will you deal with that awkward silence that may come with that first meeting? What will you talk about? Not to worry. This is completely normal. As stressful as that first date may be, we’ve got the help you will welcome.

Specifically, that help is in the form of first date questions that will keep a conversation going and make your date fun, interesting, and insightful. And by the time that date is over, you’ll know if a second date will be a good choice.

So, here we go. These first date questions are divided into categories, but here is an additional piece of advice – begin with the lighthearted and then move onto the more serious and insightful ones.

Fun and Light Hearted First Date Questions

These are the basic questions that you would ask on a first date to break the ice and make both of you comfortable and relaxed. And be prepared to respond to the same questions for them.

Now, don’t discount these first date questions as unimportant. While they are fun questions and may spark laughter, they will also give you insights into their sense of humor, values, dreams, and even tolerance for risk and adventure.

Here are some good examples of lightweight and fun questions

• If you were arrested and no explanation was given, what would your best friend assume you had done?
• What’s the weirdest food combination you have ever eaten?
• Who was your celebrity crush in high school? Is it still the same today?
• What’s the most embarrassing thing you have ever done?
• What’s your dream job?
• What’s the worst movie you ever saw? The best movie?
• What’s the last TV show you binge watched?
• What’s the best thing you’ve ever done? The worst?
• What’s something you’ve never told your parents?
• What’s one of your weird hidden talents?
• So, if you could switch lives with someone else, who would it be?
• What’s one of your biggest pet peeves?
• What’s one thing on your bucket list?
• What’s a favorite meal that you will never get tired of?
• Do you consider yourself a morning person or a night owl?
• When is the last time you took a trip for fun, and where did you go?

NOTE HERE: If you have begun to date this new person online rather than in person. these fun and lighthearted first date questions will probably be covered before you ever meet up. A person may actually prefer to begin dating this way – it’s less awkward, and they don’t have to spend time with a person who is not really a fit.

Next Level First Date Questions

You may not get beyond the low-level questions on a first date or during your online conversations. After all, you may be having lunch or dinner and maybe going to a movie after dinner. You do have to eat and watch that movie or hit that concert.

On the other hand, if you have met each other online and covered a lot of these questions already, it’s time to move onto a deeper level.

Now these questions to ask will probably probe a bit more into your date’s personality, though some may still be in the low-level category. Again, you’ll learn more, and some of these questions may be open-ended allowing for some follow-up questions. Open-ended are more interesting questions because they let a person expand on their goals, values, and beliefs.

So, here are some examples of these types of questions:

• If you could live anywhere in the world, where would that be? Why is that your first choice?
• What is your favorite thing to do in your spare time? (This is one of those engaging questions that will get them talking about something and give you insight into their personality and their passions. It might also help you find common ground – you may have free time interests that are the same or at least similar).
• What’s your favorite childhood memory? (Again, this is an open-ended question that will require them to talk about their young lives with their family). But note: if you sense that they feel pressured or feel uncomfortable talking about their childhood, change the subject quickly.
• What is your favorite holiday? What makes it your favorite?
• What is your favorite place to go when you need to unwind?
• Do you ever just take a mental health day from work? What do you do on that day off?
• What’s the most spontaneous thing you’ve ever done? Did you love it or did you regret it?
• Do you know what a love language is? If so, what’s yours? (Here, you can give a very brief explanation if they haven’t heard of this. Questions to ask might be related to each of the love languages to find out what their language is. – They’ve learned something new!)
• What TV show represents your family dynamic? Who are you in that show? (Again, if they don’t feel comfortable with questions about family, move on quickly).
• When you were a kid, what was your favorite TV show or movie? Have you ever watched reruns or that movie as an adult? Did that bring up fond memories for you?
• What’s the best advice you’ve ever been given? What advice would you give to a younger person?
• If you wrote an autobiography, what would be the title? (This can be a trigger for more conversation about your date’s life. And be sure to have your autobiography title too).
• If you life was wrapped up best in a song, what would that song be? (Again, this is a great conversation starter. Be sure that you have your song too, so you can both talk about why that song is so meaningful).
• What are the qualities you admire most in your best friend? (you’ll gain some insight into their values).

Serious Level Questions

Again, these conversations will not all take place during a date and certainly are not questions you would ever ask on a first date. They are far too probing for an early conversation, even though your date seems to be seriously interested in you. On the other hand, these types of conversations might take place if your date is just a twosome in a quiet place where you can spend some quality time together.

• Do you have an idea of where you’d like to be personally and in your career 5 years from now?
• How do you deal with conflict in your personal life or on the job?
• Are you a spender or a saver? Do you consider yourself financially independent? What’s your idea of financial health?
• What are your top priorities for your life?
• How important is politics to you? What are your political leanings?
• When things are falling apart all around you, what do you do to maintain your mental health?
• How important is religion in your life?
• What do you want written on your tombstone when you die?
• What is the worst quality someone would have that would be a deal breaker in a friendship or a relationship?

• If you were looking for a serious relationship, what qualities are you looking for? What is the worst quality someone would have that would be a deal breaker? (There is nothing wrong in having this conversation with someone you are genuinely interested in. And it doesn’t have to happen on an IRL date. If you’ve had a first or second date, you are probably calling or texting in between. This can be a conversation you can have during a phone call, and it may be less awkward that way).
• What kind of a relationship are you looking for? (Again, you have a right to know this, so that you can make sure you are on the same page before you spend the rest of your time pursuing the relationship. You should expect an honest response, and you should be prepared to be honest too).
• What would you do if parents, friends, and other family did not support a relationship you are in. Has this ever happened to you – what did you do?

This list could expand endlessly, depending on what is important to you. But you get the idea here. Now, let’s have a look at how you get at all of these questions and responses as you date someone. Here are some important tips:

Things to Keep in Mind as You Ask Questions on a Date

Most people have fun as they respond to the early questions, and you can fire them off at will. Say something like, “Let’s play 20 questions. I’ll go first, then you get to go.” This makes it a game and who doesn’t like a game? It’s something everyone enjoys since the time they were a kid.

But when you get to the next levels of questions, things become more probing. Here is some general advice.

Be an Active Listener

Whether you’re on a video call or in person, show your interest with eye contact and body language. Repeat what they have said in your own words or ask follow-up questions. This indicates that you are really interested in what they are saying to you.

Have Your Own Answers

For every question you ask, have a response too. If a question makes you uncomfortable don’t ask it of your date.

Don’t Ask About Past Relationships

If your date volunteers information about past relationships, that’s fine. But that doesn’t mean you have to. The cardinal rule is never ask until you both are getting quite serious.

Stay in Tune with Body Language

Whether a video call or in person, do watch facial expressions and other body language. If you’re not familiar with body language signals, do a bit of research. There are “open” and “closed” positions, and they will tell you a lot.

Don’t Turn Your Probing into an Interrogation

Except for those really early-on questions, do not come off like a police interrogator. If all you do is ask questions, that’s what you will look like. You know what the important questions are that you want an answer to. Space them out with conversations about other things or learn how to pose them without them being questions.

In the End…

Whether you are gay, lesbian, bi, trans, or anyone else on the spectrum, you have the right to be who you are and to date who you wish. Finding that someone or someones who are a fit for your relationship goals begins with finding out how compatible they are for your wants and needs. Don'[t be afraid to ask the right questions, move forward if the responses are to your liking and move on if they are not.