Best Online Dating Questions to Ask Him - Cool Dating Advice

Best Online Dating Questions to Ask Him

Online dating is a great thing, but sometimes it is hard to figure out exactly what to say. As women, we know exactly what we want to hear, but unfortunately, men do not think the same way as us and they want to hear different things.

You want to make sure to ask the right questions for him, but you also want to make sure that you are getting an accurate representation of what he is like.

Here are a few tips on some good questions and topics to ask and talk about with your online man.

Ask about sports

I know this is the most stereotypical subject to talk about, but they love it! Men always want to talk about their favorite sports and sports teams.


Let them tell you all about it, and you get an A-plus for bringing it up in the first place. Honestly, it’s a win-win situation.

If you actually like sports and know a lot about them, you can get to know each other a little better and have something to bond over.

Needless to say, it is always a great topic to start off when talking to men.


This topic is always important. You can see a man’s true colors by the way he treats the ones closest to him.

Ask him about his family and his childhood. This is the best way to learn what kind of person he is and what he has been through.

Family and childhood play a huge role in the person how you are today.

Learn about him and tell him about you. Just remember, if he doesn’t treat his family and close friends with respect, he won’t treat you with respect for each of her.

Make sure you chose a good one.

Guys best friend

Every guy has a wingman. Whoever this other man maybe, he will play a big role in your life once you start going on dates. Let him talk about his wingman!

Guys love to tell stories about all the crazy things that they have done with their friends.

This lets you see their comedic side and teaches you a little bit about their friends. And who knows, if things get serious, his wingman might become one of your best friends too.

High school/ college


Ask about their education. Make sure that he does not try to act like he is smarter than you or better than you when talking about these topics.

That is the first hint that he will treat you like that with everything else in life later on.

Learn about his crazy high school and college days. It is always fun to see where people have gone to become who they are now.

People change a lot over the years and it is always very interesting to learn about how they were when they are young. And if they are still young, let them tell you about their life! Education plays a big role in society nowadays.

Do you like to cook?

As a woman, you may be expected to be the one to cook. It will be nice to know if he likes to as well. Having a man that likes to cook lightens the load a little bit for you. Plus, it makes him a well-rounded man.

Who doesn’t love a home-cooked meal on date night? Cooking can also be a bonding time.

If he doesn’t cook very often, you can tell him that you both can cook a meal together sometime. It’s the little things that can be the most romantic.

What are your favorite outdoor activities?

Men love the outdoors, and many times women do too. Learn about what he likes to do for fun outside. Plenty of dates can happen outside between picnics, water parks, zoos, fishing, and so much more.

See what kind of things you guys have in common that you like to do. This always shoes him that your versatile and aren’t just the kind of girl who wants to sit inside all day. Men want someone fun.

What do you think are some problems with our world today?

This topic is a little more serious, but it opens doors to many important things when it comes to dating and relationships. Opposites attract, but it is important that you share some common values and beliefs.

Learn what is bothering him in the world today, and you will learn a lot about him and his personality.

Just try to stay away from religion and politics, because oftentimes feelings can easily get hurt and it causes problems when talking online.

Has your heart ever been broken?

To learn what kind of lover your man is going to be, it is important to know about his past. Everything that happens to you helps shape you into the person you are today.

Ask if he has ever truly had his heartbroken, because, if he has, he isn’t going to ever want to make anyone else feel that pain. And that is good for you because that means he isn’t messing around.

You could also ask him if he has ever broken anyone’s heart. This question is just as important because the trauma of relationships ending effects your new ones, and you want to see where he stands with love and where he stands with you.

This also opens doors for both of you to start talking about past relationships and exes.

At some point when you are talking to someone romantically, you have to have this conversation. It is important to get over the hump and talk about what has happened in your past.

It doesn’t need to be awkward because it was a part of your life and made you the type of person and lover you are today.

Just make sure you do this later in a relationship you do not want to talk about this the first few months of just started dating.

What is your favorite thing about yourself?

It is always good to see how much confidence and self-esteem your man has. Remember too much confidence isn’t always a good thing.

Also, this question is important because it focuses on the good aspects of him. If you focus on the bad aspects, he might make him think that you are a slightly negative person.

This conversation can lead to talking about your favorite thing about your personalities, your favorite things about each other, and your favorite things about other people in your lives as well.

You can also start talking about what kind of traits you look for in a man, or that he looks for in a woman. These kinds of questions are important and don’t ever be afraid to ask them.

You want to be honest about what you are looking for in a relationship, what you are looking for in a man, and what you like about the man you are talking to now.

What are your goals in life?

When you are thinking about being in a relationship with someone, it is always so important to make sure you have similar goals.

If he wants to move to another state and party, and you want to live here and start a family, that can cause some serious issues.

It is also important to see a want for personal growth.

Ask him about his goals at work, for traveling, with you, and just in general. This also gives you a platform to talk about what you honestly want in your life.

This is important to establish from the begging because you don’t want there to be any surprises along the way.

Where do you see yourself in 10 years?

If you really want to learn more about their goals and aspirations, ask this question.

You want to make sure your timeline of goals somewhat matches up to be a good couple. This also shows you how much progress he makes as a person, and how much he wants to make.

Don’t forget to talk about where you want to be too. All of these questions should be answered by both of you.

Do you like how this is going?

We all know that sometimes guys won’t just come out and say when they want things to end or they aren’t liking where things are going with you.

Don’t be afraid to ask these questions because you don’t deserve to be led on. At the same time, make sure you are open with them and let them know if you don’t like how things are going with them.

You can ask a bunch of fun and an interesting question like these.

Do you have any odd talents?

This is a good question to see if they have any interesting gifts. They may come from an acrobatic family and maybe he used to be a trapeze artist.

You never know what someone is into or what hobby they may have that is fascinating. That is why this is a good question it will spark some conversation for a while.

Would you rather go bungee cord jumping or white water rafting?

Fun question what would really be interesting if he has already done both of these. I know when I have done both in my life which they were both really fun.

This will tell you if he is a daredevil or likes outdoor activities. If you like the same kind of things that is something you can both build on.

What were you like as a kid?

This is a good one to see how he was raised. Maybe he grew up on a farm where he was up at 5 AM feeding cattle.

Going back to childhood will be hopefully good unless they had a bad childhood. If you ask the questions and he gives a short answer then move on maybe things were not so great as a kid.

Pick one vacation in Fiji or mountaintop ski resort

Give some random places to pick for a vacation to see which one they will choose. You get a sense for what they like to do and where they like to go.

I like going to beaches especially the Caribbean but other men may like mountain cabins or French Rivera. Everyone is different so talking about where to travel and what he likes would be a fun thing to discuss.

What is the best prank you have ever done?

This should be something fun but hopefully, they did not do anything too illegal.

We bombed our High School band with water balloons as they practiced on the field. The balloon would hit in the middle they would move out of formation then quickly get back into formation.

They got tired of it at one point and the band director said go get them so they ran after us. Good old high school days when you usually do stupid things.

What superpower would you want and why?

I know I would want to fly as my superpower. I could take trips anywhere in the world and travel would be free. I just have to watch out for low flying planes or birds. What superpower would best fit you?

If you could go back in time to peak on history what time period would you go to?

This would be incredible if you could do this. What would you do maybe go back to the time of Jesus, check out the pyramids being built or watch the signing of the Declaration of Independence? So many to choose from where would you go?

Name something everyone in the world should experience at least once?

Hopefully, they say something like the love of a family. Knowing guys it will be something like riding the tallest roller coaster in the world. I think it depends on the age of the guy what answer you will get on this one.

What random acts of kindness have you seen or think people should do more of?

This gives you a sense of where their heart is in today’s world. There are so many bad things going on in the world looking at acts of kindness gives humanity a boost.

Helping Others

Do you have a skill that is super useful?

Many people have a skill that is useful so what is their skill. Maybe they are skilled at tennis, badminton or chess. It is always good to know what someone is skilled in life.

I am a really good street fighter which is not a skill too many people have. I have trained for 20 years in different fighting systems so that is why I have a unique skill.

It is not very useful for every day purposes because I never have to use it but if I do need it that could be a lifesaver.

What is your skill?

You can ask more serious or probing questions like below just make sure it’s not too probing. When you first get to know each other you will want to take things slow.

Name something in your life that was a big impact?

You want them to kind of open up about things in their lives and how they dealt with it. This may be too deep for email conversation or when you first meet.

You may want to wait to ask this question when you have met and gone out a few times.

What is the cause or charity that you can really get behind?

You can really see what they stand for and what has real meaning. Remember you might want to ask this question when you have gotten to know them better.

If you passed away what would you say was great about your life

This is deep talking about your own demise but it will get you thinking. Maybe you could open up by answering the question first and then they can answer. You do not need to be morbid about it just say things that were great times in your life.


Overall, just make sure that you are getting to know your man well. It is critical to focus on what is important to you when looking for a man.

Make sure you are asking questions that make him feel comfortable and relate to his life. Online dating is fun, you just have to know all the right (and wrong) things to say.

Guys act like were the hard ones, but we all know they’re just as difficult as us. Have fun with your online conversations and make sure you found a good man. You can also read our article on 10 tips for how to date online.

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