Online Dating Questions We Know Will Work For You

Smartphone - Dating Site Profile - Speech Bubbles

If you are someone who is using online dating sites, you will no doubt know that everyone is out there vying for everyone else’s attention. Something that you can be doing to experience success is sending engaging icebreaker questions when you speak with someone online for the first time. These have to be questions that not only catch someone’s attention but also generate good, sustainable conversations!

We have found that the bulk of online dating apps users will initiate a conversation with someone new using generic messages like “hey,” “hi there,” or “how are you doing tonight?” These are not messages that are going to stand out or get you noticed! In fact, a message like this is going to blend in with all the other messages just like it!

Here is how you can stand out.

Take to someone’s online profile and find out whatever you can about them. Then form a good, thoughtful icebreaker question around something that you learned from their profile. It’s really not that hard to do. All it really requires from you is a bit of initial research and some sincere words!

It’s also going to show someone that you actually took the time to look at their profile and learn something about who they are! We are going to show you a few examples of some of the best online dating questions we know for breaking the ice!

What Are You Looking For on This App?

This is definitely one of the most direct questions that you can ask someone you just met on a dating app, but it can quickly establish if certain people are going to be worth your time and effort. A lot of people will make this clear in their dating profiles or online bios, but it never hurts to make sure and firm this up with someone.

By asking this question, you can get an idea of someone’s end game using the app. If someone’s goal matches up with what you are looking for, you can proceed with developing a relationship knowing there is some potential there! Asking this kind of question can also establish you as straightforward and as someone who knows what you want. People will know that you are not interested in playing games!


“Hey, Julie. Out of anyone I have been matched with on this app, you are the one who really caught my eye. I’d love to get to know you better. But you should know that I’m the kind of person who does not like to waste time. And I certainly would not want to waste yours. I have to ask you. What are you looking for on this app?”

Where Is Your Favorite Place in the World?

Someone’s “happy place” or the place they go to relax or go on vacation are places that can put people in a positive frame of mind. If they are in a positive place when they are talking to you, they might begin developing positive feelings towards you. So asking them about these places is a good way to start out an online conversation in the early stages of a relationship.

The Aurora Borealis
San Francisco in California - Cable Car Street
Kauai in Hawaii
Road Trip - Street - Forest - Mountains
Time Square, New York City
Red Rocks Park in Colorado

As we mentioned earlier, it is good to do some research on someone’s online profile before you begin talking with them or attempting to break the ice. A good way to wind up asking someone about their “happy place” or their favorite place on Earth would be to look through someone’s photos and see if there are any interesting places they have visited in recent years.


“Hey, Carly. I was glad to see I was matched with someone who likes mountain climbing as much as I do! My favorite place in this world is Red Rocks Park near Denver. Hands down. Where is your favorite place of all time?”

What Are Your Pet Peeves?

Depending on whom you are talking with, asking someone about their pet peeves could generate a lot of good content for conversation! People generally love talking about the things that get under their skin. Asking this question is always a good way of getting someone talking, even someone who is shy or soft-spoken!

When you are checking out someone’s profile or bio online, there is a good chance that they might have some of their pet peeves listed out for all to see. Let’s say you’re checking out a girl’s bio, and she states her disdain for people who cut her off in traffic. You can take this information and form a good icebreaker question, something like this.


“Hey, Sarah. It looks like we see eye to eye on crazy, overly aggressive drivers and heavy traffic. We’re kindred spirits! What are some of your other pet peeves? I’m going to do my best to avoid them. LOL.”

What Is One of Your Proudest Accomplishments?

This is a great icebreaker question for many reasons. For one, it is guaranteed to get a strong response. People typically are never too hesitant to share things that they have done well over the course of their life! This question can give you a sense of what someone values in the world, be it relationships, career-related matters, or personal success.

But how can you work this question into one of your first conversations with someone online? There are a few ways that it can be done, but we will use an example centered around someone’s career path.


“Hey, Rachel. I saw that you are a lawyer just like me! I had to ask you. What has your great accomplishment been at this point in your career?”

What Does a Typical Saturday Night Look Like?

With this question, you can find out if someone goes out and gets crazy with their friends on the weekends or if they are more reserved and like having a nice quiet night in with some Netflix in their pajamas.

By asking this one, you can gather some ideas for future dates! If someone is more energetic and apt to go out on the town during the weekends, the possibilities for dates are endless! If they prefer staying home and relaxing, you could plan on making a meal together and relaxing with the Harry Potter movies or something like that!

How does this icebreaker get worked into an early conversation? Here’s a good example of how you can work it organically into one of your first online messages.


“Hey, Jen. I see that you like playing tennis and we seem to have the exact same taste in movies. It would be really fun to hang out sometime soon. Let me know what you think. What does a typical Saturday night look like for you?”

What Do You Do for a Living?

People spend most of their adult lives working, so it’s only natural that jobs and careers can be a huge source of material for conversations. You can find out if someone enjoys their job or finds it unfulfilling, having the desire to be somewhere else in their career or in a different job field altogether.

You can find out a lot about someone when you ask about what they do for a living. You can get an idea of their work ethic or how well they work on a team. You can also find out where they went to school and what kind of education they hold.


“Hey, Valerie. I saw in some of your profile pictures you were wearing scrubs. What do you do for a living? I work in the medical field myself!”

What Are Three Words That Best Describe You?

This icebreaker question can be a really fun one to ask the first time you talk with someone online. It is a random icebreaker that can catch people off-guard, but it is one that gets people excited about it, and they quickly get to thinking about their top-three words. This one is best asked right away without much lead-in.


“Hey, Kristin. Three words that best describe you. Go!”

The three words that someone chooses to use can be indicative of the kind of person they are, and you can get a decent idea if this is someone you want to continue a conversation with going forward.

What Is One of Your Life Mottos?

This question could even be phrased, “Finish this sentence. My life motto is…” This question can give you a really good idea of what someone is all about, how they see the world, how they handle problems when they arise, and their general approach to living.

How can this one get worked into a first conversation naturally? Let’s take a look at this example below. You could outright ask someone these questions, or you can build up to it a little bit in a concise manner.

Life Motto - You Didn't Come


“Hey, Ashley. I’m going, to be honest. I took one look at your profile picture and found you to be so stunning that I almost didn’t message you! But I decided to anyway because you only live once, right? That’s something I try to live by. What’s one of your life mottos?”

Do You Think You Would like to Be Famous?

This question can be a decent gauge of how important status or wealth is to the person you are messaging. Their answer could be telling of their aspirations in life. It’s also a good way to find out if the person you are speaking to is indeed an extrovert or an introvert. Plus, this one has some good potential for fun back-and-forth as the two or you visualize what it could look like living a life of fame and fortune.


“Hey, Kara. I don’t know if you watched the Queen’s funeral this week or not, but it was beautiful… and BIG. I don’t know that I would ever want to be that famous! Do you think you would ever want to be famous?”


Forming a good online dating question is not all that difficult. You need to take the time to look at someone’s online profile and find something that you can base your icebreaker around. We guarantee that tying the question in with something you read on someone’s profile is going to make you stand out in the midst of all the other boring messages they are getting from other singles on the app!

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