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!

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?

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?
• 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?
• 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?

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.)
• 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.)

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?
  • Where do I stand with physical intimacy?
  • Would I let someone pick me up on the first date?
  • Am I comfortable giving out my phone number before the first date? (You can always chat on the app.)
• 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.

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