Best Online Dating Questions to Ask Her - Cool Dating Advice

Best Online Dating Questions to Ask Her

Online dating can be a great thing. But, sometimes it is hard to know exactly what to say. Especially when talking to women, it may feel like you are very worried about saying the wrong thing. What are the best online dating questions you can ask her either online when messaging or on a first date? You want to ask fun questions would be the number one thing you could ask. You can ask questions based on their profile and what they like would also be at the top of the list of questions to ask.

Things can be perceived very differently online than in person and sometimes it is hard to know exactly what to say. You want to make sure that you understand what kind of things you need to do to make this girl feel like she is the only girl in the world. Here are some topics to help you with his.

What is Most Important to You?

It is very important to see where a girl’s values are.

Is her job really important to her? Is her family?


Her education?

These are the kind of things that you need to find out in order to learn the most about the girl you are talking to. You can learn a lot about someone by asking this question. You also want to make sure that you tell her what is most important to you as well and why. Make sure that if you talk about this, you both explain why this specific thing is so important to you.

Values and beliefs play large roles in relationships and dating.

What Have You Learned from Your Mistakes?

This question can bring out some vulnerability in both of you. It is so important, to be honest, and talk about the mistakes you have made in the past. This gives both of you the chance to explain how you have grown as a person, and how your mistakes and failures have made you who you are today.

You can learn so much about. A person by how they react. Do not be ashamed to admit these flaws. No one I perfect and women love it when you fess up to your mistakes because it makes you seem more approachable and down to earth.

Tell Me About Your Friends

You can tell so much about someone by who they surround themselves with. It is so important for you to hear all about her and her friends and for you to talk about yours as well. If this relationship goes further, these people are going to be a part of your life and it is important to know how much time they spend with them and what they’re like.

This also opens up opportunities to start sharing all the fun and crazy stories of things that each of you have done with your friends.

Tell Me About Your Childhood

In order to fully get to know someone, you need to learn about their family and childhood.

The family is so important in a relationship because you are getting in a relationship with their family too. Let them talk about all of their grandparents and how they spent holidays growing up. This is the biggest opportunity for you to see why they are who they are today and who helped them get there.

Let them talk about high school, and how they were the head cheerleader.

Let them talk about Friday nights, and how they were crowned prom queen.


These kinds of things are fun to talk about and fun to learn about. But don’t forget to share all this information with her too. All of these questions you should be answering you as well want both of you to know all of this about each other and have the opportunity to grow as a couple.

This topic also opens doors to start talking about college and education.

These are important topics because you want to know how seriously they take their education, and you want to know what they’re passionate about. Or, maybe they hate their job and want a new one.

Let them talk about their lives, jobs, and problems to learn about their character. Tell them what you do and what makes you passionate and how that can benefit them.

What is Your Idea of a Perfect Date?

The little things are so important to women.

Meaningful gifts and dates are the way to their heart. If you ask about this, remember, and execute the date that is a for sure way to please her.

You also want to know if she wants to dress up and go to a fancy dinner or sit at home with a homemade dinner and a football game. You need to get to know what she likes on a personal level and find some similarities that you can bond over.

You can also tell her what your favorite dates are so that she can try to make you happy as well. Don’t be afraid or embarrassed to ask these questions because they are important.

What Means Most to You in a Relationship?

You want to make sure that you know what is most important to her in a relationship so that you can focus on that and never make her feel bad about herself or the relationship. You want to make sure that you feel capable of giving her what she needs to be happy and vice versa. You want to learn this soon into talking so that you don’t hear each other in the end if you guys end up not clashing together.

Women like when you show effort.

The simplest task of asking these questions shows that you care and that you are trying to make her happy and make this a good relationship.

Women like reassurance, so make sure to tell her that you’re not messing with her. Make sure to tell her that you are asking her these questions because you honestly care how this ends up.

Be a nice guy and make her happy and you’re set. That’s all a girl wants.


This topic is where you can find some similarities and some good date ideas.

It is important to know what someone does in their free time because this is what makes them happy. Whatever their hobbies are, are not going away. So, make sure that you don’t say anything negative about them because they will always have these hobbies and they are probably very passionate about them.

You never want to make her feel like she should be embarrassed, or you think something that she loves is stupid.

What is Your Most Embarrassing Story?

Take some time to get to know one neither and talk about embarrassing things that each of you have done.

Once again, women like men who can admit that they are wrong. It is bot attractive when someone acts like they are better than you and have never done wrong.

This can be fun!

Don’t be afraid to share actual embarrassing stories because if you stay together your mother was bound to tell her anyway.

Do You Like to Travel?

People nowadays love traveling.

Ask her about where she has been and where she wants to go.

Maybe you two can plan a small trip together. You can start talking about dream vacations and learn about all the exotic places she wants to visit. It is important to know what expectations she has about life and traveling because this will affect any relationship.

Be open with each other and tell each other what you need to do, and where you need to go to be happy. Happiness is key.

What Are Some Accomplishments That You Are Most Proud Of?

It is important to know what she has worked hard for, and if she appreciates her hard work.

Confidence is always attractive as long as it isn’t too much.

Don’t be ashamed to share with her the things that you have worked hard for in life. Women know that if you are a hard worker at work or with other relationships in your life, that you will work hard for your relationship with them too.

What is The Hardest Thing That You Have Overcome?

Here is where the two of you can get personal and talk about some obstacles in your life.

Women like when men are vulnerable and not afraid to show their emotions. Showing your emotions and talking about your obstacles, shows so much about your personality and character.

Show that you care about her past, even though you were not a part of it. You have to learn about what someone has been through to know them as a person. Open up, and she will appreciate it.

What is your goal in life

This will really tell you a lot about a person. If they say they want to work a pot dispenser so they can smoke weed all day then this may not be the right person.

What do they want to do with their life when it comes to career, family and overall life ambition. A question as deep as this one will really help you understand who you are dating and if you think the answer fits for a second date.

When you were a kid what were you like

Everyone was a kid and has some great stories about being one.

This will take the person back to their childhood which hopefully was a good one. They may tell you some funny or entertaining stories that give you a glimpse of the person you are with.

What is your purpose in life

Do you have something you really want to do?

Maybe you want to be a politician to help people out in your state. You want to be a surgeon so you can save lives. What is the singular reason for your existence?

Name your favorite types of vacations

You ask them where and what do they like to do when on vacation. They may like the beach and sand with the ocean.

Skiing in the mountains may be the adventure they love.

Whitewater rafting down the Colorado River is something that really excites them.

RV camping across the country could be the big vacation they are looking to do.

The places you can go and see are endless. This will be a great conversation when talking online to get to know each other.

Tattoos and scars

These both will definitely get a conversation going. You talk about a scar and every scar definitely has a story. If it is a really bad scar they may not want to talk about it so be careful.

Tattoos will also be a fun one. People usually get tattoos for a reason so hearing that reason will be fun.

Here is a fun one do you like dogs or cats more?

This will be a fun one especially if the person asking the question has a pet that the woman does not care for as much.

Maybe the date likes dogs and you own a cat. Not that you can’t like cats it is just your preferred dogs. You can be safe and say you like them both the same. That is the safe bet if this question is asked.

What do you like to do the most on the weekend

Maybe she likes to watch college football games.

My daughter loves college football and watches with me all the time.

Shopping and lunch may be her thing to do on the weekend. Whatever she says will definitely tell you what she likes to do in her spare time. Hopefully, you at least have something in common with what she says she does.

What is your favorite alcoholic drink and what is your favorite non-alcoholic drink

We have two questions that can be asked when getting to know each other.

Hopefully, her favorite alcoholic drink fits with what you like. I like pina colada drinks so maybe she does too. It’s not that big of a deal if she likes fruity drinks and you like drinking beer.

Non-alcoholic drinks could be soda they like?

Tea has gotten popular so maybe you both like tea. Find common ground on what you both like. You will not like everything the other drinks which is fine. The great thing is you know what you need for the fridge when she comes over.

What is a subject you can talk about forever

Hopefully, once you ask this question they do not go on and on about that same subject. The worst is they keep talking about it and will not stop. You want an answer that they may say they love talking about the universe. I like the universe too so talking about it would be a great conversation.

Are you competitive

This is good to know because she may be hyper-competitive and rip your head off when playing the next board game.

It’s fun to be competitive but sometimes you just need to play for fun This question can lead into what they are competitive about when doing a competition.


Overall, it is important to make sure that your date knows that you are trying to get to know her and trying to please her. Do everything you can to find out what she needs to be happy. The effort is so attractive to women.

Pay attention to how she is talking to you and treating you because odds are that she wants to be treated the same. Treat her with respect and show her that you can make her happy. Women are not as complex as you might think, they just want someone to genuinely care for them and their happiness.

You can also check out our dating website review section.

Here are a few more articles that you may like:

Online Dating When to Meet Someone in Person

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