What are the best online dating icebreaker questions? - Cool Dating Advice

What are the best online dating icebreaker questions?

It’s never easy to date someone for the first time. You may get nervous at first because you do not know what to say. You don’t know them so of course, you may have tons of question to ask them. I’m here to tell you don’t think so hard, it’s way easier than you think. You don’t want to be too nervous and give off wrong impressions. Note that first impressions are everything, they can make or break you.

Since you’re online dating, communication is very important. What are the best online dating icebreaker questions? Questions that make the other person think and maybe even get them to laugh when they give you an answer either through email or on a date. If you can pique their interest with some great questions then you can move forward in the relationship. 

So what are the best online dating icebreaker questions? It’s important when you ask your date questions for the first time they aren’t too serious and “investigator like.” You don’t want them to feel like they’re in a Law and Order TV serious.

You have to ease into the more serious and personal questions as the conversation goes on. You also don’t have to play it too safe because that can be boring and since this is online dating you don’t want your date to fall asleep at the computer. So below are ten simple and fun icebreaker questions you can ask. These questions allow you to get to know them without them feeling interrogated.

What do you like to do for fun?


Asking someone what they like to do for fun is a harmless question that can get the conversation started. It’s not a serious question so the person responding to the question does not have to hesitate to answer it. Although, most people do have a difficult time answering this question, especially if their lives is work, home, and repeat.

If that is the case, you can get an idea of how they organize their time. If they do not have a lot of fun maybe you could be the person to bring spontaneity to their lives. Also, asking this question indirectly gives ideas on what to do when you have a date in person.

What’s your favorite restaurant?

This is another harmless question that allows you to get an idea of the types of foods they like to eat.  This also will let you know where to go if you both go out to dinner for your first date. Besides who doesn’t like talking about food? Food makes people happy.

What music do you like to listen to?

We can all agree that music is an important part of life. Music can bring everyone together to have a good time. Everyone has their own preference for music and in a way, the type of music you listen to can determine what type of person you are.  So asking this question may give you an idea of what their personality may be like.

For instance, some people may say they like all genres of music. This could mean they are open-minded and don’t mind trying new things.

Some people may have a particular type of genre they like to listen to, such as classical music or smooth jazz. This could mean they are the laid back type.

Many people may like rock and roll or rap music. This could mean they are outgoing and love having a good time. Therefore asking this question will give you an idea on the type of person they are.

Please don’t think you completely know a person because they told you the type of music they like. This question just give you an idea, you still have to get to know them some. So continue asking questions.

Have you traveled outside the country?

This is a very adventurous question. Who doesn’t like traveling? You should want to know how much the person you’re dating has seen the world or if they are even interested in traveling. If they have traveled a bit you can expect to hear some very cool stories.

Some stories may even wow you.


Or some people could be content with staying within their city limits, and that’s okay.  If they do say they haven’t traveled much, let’s hope they are open to doing so. Why? Because everyone should get out and experience the beauty of the world.

There’s more to life than just staying at home.

If you could live anywhere, where would it be?

This is the perfect question if the person you are dating lives far away. You may want to know if they will be willing to live somewhere you’d like to live.

This is just in case things get serious and you can’t take the long distance anymore. You may start thinking about where you both would live, rather live in each other cities or move to another city together. But, don’t start thinking too serious yet.

This question is only supposed to generate expectations for the future. You never know, the person you are dating could have dreams to live in Alaska and that’s probably not in your future, or it could be.

Do you have any family traditions?

At this point, you are starting to get to more personal questions. You are at the point where you can really get an idea on who they are.

Family traditions are important.

You’re going to want to know if the person you are dating has any traditions of some sort. You may or may not agree with them. For example, you could be an atheist and the person you are dating is a Christian and like to attend church every Sunday.

The question for you would be, are you content with knowing you’re an atheist and your partner is a Christian?  If you both have any differences in traditions this could be an issue down the road, especially if you don’t respect each other’s values. The key word is “respect.” Regardless of anyone’s family traditions respect their ways of practice, even if you don’t practice them.

What’s the craziest thing you ever did

This is a spontaneous question, just in case you think the conversation is getting too serious. This question should spice things up a bit and lighten the mood. This question will let you in on their wild adventurous side or they probably played it safe their entire lives.

Either way, you are getting to know them and their experiences in life.

Hopefully, the craziest thing you have done isn’t too crazy that it makes you back off. Just know that if you ask this question be prepared for any answer you may get. You opened yourself up for this, so leave all judgment out the window. This is all about getting to know each other.

If you were granted one wish what would it be?

This is a very intriguing question because in some way it tells you what a person needs or wants. Most people will say they want millions of dollars and that lets you know the person is in need of money and lots of it.

Another person may say they wish they could bring a loved one back and that could mean they’re still grieving from a loss and could use a good friend.

Some people may wish for some type of superpower, this could mean they need to tackle certain things in their life with invincibility. Whatever they wish for, try to read between the lines to get an understanding of what they want.

What do you like most about yourself?

This may be a complicated question to ask but at this point, you’ve asked all the fun questions. It’s time to get a little serious now.

It’s very important to know how your potential partner feels about themselves. This question can highlight any red flags you probably didn’t catch before. If a person can not tell you what they like about themselves they could be battling with self-esteem issues.

It’s not to say they aren’t ready for a relationship,  they just have some things they need to work on within themselves.

What are you looking for in a partner?

This is the question you are leading up at the very end of the conversation. After all the questions you have asked this is the last question of the conversation.

This question lets you know what they are looking for in a mate. With this question, you are trying to see if you have the qualities they are looking for. It could be a nice sense of humor, a great smile, a person that is consistent, reliable, mature, funny, or intelligent. Whatever it is you are curious if you meet the requirements or not.

In any healthy relationship, you want to make sure both of you are satisfied and content with one another. If you ask this question, hopefully, they don’t have shallow standards but is more realistic instead.


When you are looking for someone online to hopefully start dating. The key is to ask really great questions during the email phase of the connection online. Ask meaningful and some probing questions that will really let you know who this other person is as a person so you can make a decision as time goes on if you should meet face to face. That should be the ultimate goal to meet and start dating. You can also keep using icebreaker questions even when you meet face to face it’s just most of the time you will be talking online before a face to face meeting.

17 Casual First Date Ideas



Recent Posts