Questions to Ask When Online Dating

Has online dating ever felt like a never-ending stream of job interviews? You ask the same questions, get the same answers, and never really get that far in getting to know someone or validating if they’re worth your time for a date.

Good news—you’re not alone. But even better news is that we’re here to help. In this guide, we’re going to outline the best questions to ask when online dating. We’ll talk about questions to ask a new match (before you meet), questions to ask on a first date, and even get into some questions you should be asking of yourself before you take the leap into the realm of online dating. Also, we’ve added a section on questions that you shouldn’t ask, which can be just as important.

We’d ask if you’re ready to get started, but there are already enough amazing questions in this guide that we’ll spare you one more!

A Young Black Couple Asking Each Other Questions

Questions to Ask When You’re Not Getting Results

Online dating is not a lot of fun when you aren’t getting the results you want. Maybe you’re not meeting enough people? Maybe you’re meeting the wrong kinds of people? Maybe you’re struggling to find someone to go on a date with? Whatever it may be, it’s not the results you want!

But that doesn’t mean it always has to be that way. Here are some questions to ask yourself to find ways to improve your results when dating online.

  • Am I using a quality dating app? If you’re only using a free dating app or one without a great track record, you’re not going to get results.
  • Am I actually putting in an adequate amount of effort to attract the kind of people I’m interested in?
  • Does my dating profile show effort and accurately portray who I am and what I’m looking for? If you aren’t sure, check out our guide on how to write a dating profile.
  • Am I trying to hard and pushing myself toward emotional burnout? This is far more common than you might think. Check out our data on emotional burnout from online dating.
  • Are my expectations realistic? Remember, online dating is way more of a marathon than it is a sprint.

Questions to Ask a New Match

Talking to someone new online is exciting. You never know when you’re going to be talking to that special someone that you might spend a lot of time or even the rest of your life with. But how do you best get to know them? How do you make sure they’re worth your time for a first date? How do you make sure you’re setting yourself up for success?

Well, the answer to these questions is more questions. Here’s a lengthy collection of some of the best questions to ask a new match when dating online. Keep in mind that you don’t have to ask all of these, but just pick and choose the ones that are the most important to you. Also, feel free to reword them if you need to in order to better fit you.

  • What are you passionate about in life?
  • What short and long term goals do you have for your personal and professional life?
  • Would you consider your values more traditional or progressive?
  • What scares you/what’s your biggest fear in life?
  • Are you religious? If so, how big of a role does it play in your life? (Yes, it’s okay to ask about this. Avoiding these topics because of antiquated guidance is just a waste of your time.)
  • How do you like to spend your weekends and your free time?
  • Ask questions about things on their profile that are interesting to you. (This also shows that you read their profile, which usually means big brownie points.) Example: I saw on your profile you said you love dogs. Do you have any pets?
  • Are you a spontaneous person or a planner?
  • Do you tend to focus more on the big picture or the little details?
  • What do you do for a living/what kind of work do you do? (Notice we didn’t say “Where do you work?” That can be a little too personal when you’re first getting to know someone. There’s nothing wrong with asking what they do for a living, though. They are two distinctly different questions.)
  • What’s your schedule normally like? (This is a great question to ask when you’re transitioning into looking to set up a potential first date. It’s also nice to know for general information.)
  • Do you prefer going out or staying in more?
  • Do you prefer being inside or outside more?
  • What kind of sense of humor would you say you have?
  • Would you consider yourself a morning person or a night owl?

Questions to Ask on a First Date

Some people like to really get to know someone before they meet up, and some people like to chat for a very limited amount of time and get to know each other in person. If you are in the first group, you’ve already asked a lot of the questions in the previous section. If you’re in the latter section, make sure you use some of the questions from the first section on your first date since you probably haven’t asked many or any of them yet.

In addition, though, there are some great questions you can ask on a first date. These questions can also be asked online, but they’re ones we feel might be better to talk about in person.

  • Tell me about your family. Are you close with your parents? Siblings? Big family or little family? (Don’t be off-put if they’re hesitant to talk about their family on a first date. Some people are a little more private on these things.)
  • How do you enjoy what you do for a living? What’s a typical day for you like?
  • Do you have a lot of friends you split your time between or just a few close friends?
  • What’s your biggest dating pet peeve?
  • How long ago was your past relationship? (Note: don’t let this devolve into talking about exes. You just want to find out if you’re at risk for being a rebound.)
  • How long have you been dating online? Any funny or awkward stories so far?
  • What kind of food do you like to eat? Do you normally eat super healthy or are you a foodie? What’s your favorite food? Are there any foods you absolutely don’t like?
  • Did you grow up here? Is your family local?
  • Do you enjoy traveling? What’s been your favorite trip so far? Anywhere you would like to go one day?
  • Do you have a favorite holiday? Why is that your favorite? (Take note, this question can actually tell you a lot about someone).
  • What’s the coolest thing you’ve ever done in your life, and don’t worry if it comes off as bragging?
  • What’s your absolute favorite story to tell?
  • What are you most proud of in your life? (You can let them know it’s okay to brag a little when they answer if you want to.)

Questions You SHOULDN’T Ask

While there are so many great questions to ask a new match when dating online, there are quite a few that you should avoid. And these questions should also be avoided when it comes to a first date. Down the line, yes, these almost all will be important questions (with a few exceptions). However, they’re not great for someone you’re just meeting.

  • Tell me about your last relationship/your ex.
  • How much money do you make?
  • Anything about politics. (The one exception here is if politics is just that incredibly important and critical to your life where you can’t spend a minute with someone who doesn’t share the same views as you. Additionally, if politics is a deal breaker, you might as well find out if things are a match or not.)
  • Anything overtly sexual. (The exception here is if you met on the pretenses of a casual and physical relationship. If that wasn’t directly discussed online, though, keep it PG.)
  • Where do you live? (Some people aren’t comfortable with this information early on, and you probably shouldn’t be either for safety reasons. A better question to ask is “What side of town do you live on?”)
  • What did you like about me? What made you want to go on a date with me? (These sound like you’re fishing for a compliment and make you sound unconfident. They’re very unattractive questions to ask.)
  • What kind of guys/girls do you typically date? (There’s just not a whole lot of good that can come out of this question.)
  • Questions with no substance that you don’t really care about the answer to. For example, what’s your favorite color? While you’ll probably learn this down the road if you date this person, is that really critical to your first date or seeing if you want to go out with them? It’s the equivalent of talking about the weather (unless there is something out of the ordinary going on.)
  • Are you having fun? If you can’t tell if they’re having a good time or not, asking won’t help your cause. Pay more attention to their non-verbal cues.
  • Anything accusatory. For example, if they showed up late—why were you late? While being late is rude, it’s not a great idea to call someone out on that via question.

What happens if my date or match asks me these questions?

It’s up to you how you react to that. Some people haven’t had the privilege of reading this guide and just might not know better. Always remember that you can politely decline answering and questions you don’t want to. Easy responses include:

  • We can probably talk about that later if we see each other a few more times.
  • I usually like to wait until later to talk about that topic.
  • I’m not really comfortable talking about that just yet.

Questions to Ask Yourself

A lot of people jump headfirst into online dating without taking the time to get all their ducks in a row. And while we’re advocates for taking the plunge, there are some questions you can ask yourself before you get started to make sure you’re setting yourself up for success.

Here are several fantastic questions to ask yourself before you start dating online.

  • Am I emotionally happy enough with myself to be vulnerable in a dating environment? Am I using dating to try and fill a hole in my life? Do I want a relationship or need one? (If it’s the latter, you should probably pump the brakes and work on you first. Relationships are supposed to be complimentary to your life and happiness. If it’s a want instead of a need, you’re good to go. If it’s the other way around, work on you first.
  • What are my goals with online dating?
  • Am I looking for something casual, serious, or in-between?
  • What are my absolute deal breakers?
  • Do I have a plan in place to safely date online? Read: Our Online Dating Safety Guide
  • What am I comfortable doing?
  • What am I looking for? (This may sound super basic, but the more exact and detailed you can get in your answer—the better. Know what your wants are and what your needs are. Be careful not to fall into the trap of creating a dating checklist that might make things harder for you.

The more of these questions you can have figured out before you get started with online dating, the better position you’re going to be in. It’s like the old country song says—”You’ve got to stand for something or you’ll fall for anything.”

The Bottom Line – Avoid the Interview

People get nervous on first dates. It’s inevitable, and it’s okay! The temptation in those situations can be to worry more about what you’re going to say and not actually listening.

When you ask these questions, listen to their answers. It’s great if you’re able to find follow up questions or even situations where you have things in common. Try and find the happy balance of talking and listening, and when you’re listening—actually listen and process what they’re saying. The worst thing you can do is just read through these questions one by one. That’s how you end up getting that unnatural job interview feel.

Matt Seymour

Written By: Matthew J. Seymour, MSF

Matthew J. Seymour is a dating industry expert with over a decade of experience coaching singles, reviewing dating apps, and analyzing trends within the industry. Matt is a published author with his most recent work “Get More Dates: How to Master Online Dating Apps” that hit shelves in 2023. With a Masters of Science in Finance (MSF) degree from the University of Florida and extensive knowledge of the innerworkings of the online dating industry, Matt frequently serves in an advisory role to some of the largest dating apps on the market. In Matt’s current role with Healthy Framework, he leads the interview team that regularly interviews key dating industry leaders, and leverages his financial knowledge and dating app experience to review and share what singles need to know to get the most out of dating online.

Rychel Johnson, LCPC

Reviewed By: Rychel Johnson, M.S., LCPC

Rychel Johnson, M.S., LCPC has extensive experience in the mental health and personal empowerment fields. With a Masters Degree in Counseling Psychology from the University of Kansas and over a decade of experience in private practice serving adults and teens, her expertise in dealing with dating and romantic relationships is extensive. Rychel is a licenses clinical professional counselor in Kansas and has started a a local therapist collective in Kansas to help establish community and mutual support. In addition to all of this, Rychel is an integral part of the Healthy Framework team ensuring articles and knowledge around dating and dating apps are accurate, safe, and helpful.