10 Great Online Dating Questions for Women and Men

Developing deep relationships these days is harder than it ever has been in the past. The internet and social media make it easy to meet, but hard to get beyond the surface. In a fast-paced world, it’s important that you get your online dating questions right.

By using calibrated questions that give you plenty of information about your online flirt in a short amount of time, you can avoid wasting time with the wrong person. This will save you effort and even help you fall in love faster.

In this article, we share our personal favourite questions to ask for online dating success.

Differences in Online Dating Styles for Women and Men

Rather than provide a generalized list of ten online dating questions, we wanted to target specific questions for the opposites sexes. Women and men think differently, so providing our unique perspectives will help you with whomever you’re after.

This comparison between the dating styles of women and men is a guide for visualizing the differences:

We recommend keeping this graphic handy as it will keep you from making relationship mistakes based on communication gaps.

Online Dating Questions a Woman Should Ask a Man – Cassie’s Perspective

Men can be very aggressive with their dating style, particularly online. Behind the screen, it is easy for him to be pushy and state what he wants.

As a woman, it is vital to keep your own needs in mind with your conversation style. Is he giving you room to talk about yourself, or is it a high-pressure sales job? The questions below will help you see who truly rises to the top. That will be someone you find interesting and, just as importantly, someone who finds you interesting.

1. What do you consider your best quality?

This is always a great starter question and an easy icebreaker, as it will give you insight into a man’s personality. A shy man may struggle with answering such a straightforward question as it may feel like bragging or embellishing, whereas an overly cocky or confident man may never turn the conversation back to you.

Someone who can answer the question honestly, yet humbly is likely someone with whom to continue the conversation, assuming you like what you are hearing.

2. Why did you decide to look online for love?

There are countless reasons why many are turning to the internet to find love in today’s connected world. It is certainly an easy solution given the abundance of apps and social media platforms.

Here are three basic reasons a man might try online dating:

• Convenience. Spare time is rare, so being able to find a woman online is uncomplicated.
• Lifestyle. They might not frequent places that opportunities for finding love connections are presented.
• Variety. Perhaps they’ve dated everyone in their social circle and have run out of options.

This question can further explore the type of life your potential match leads and whether or not it aligns with yours.

3. Are you close with your family?

This seems like simple small talk, yet can give you a view into what a future with your online connection may hold. A person who is not close with their family may signal that there may be strife or drama that you may not wish to be entangled within.

Someone who is too close can present a different set of problems.

This is likely a conversation that will happen further down the road as your relationship grows but having a sense of what is ahead may help ward off unsuitable partners before you become too attached.

Related Reading: Does the Approval of Friends and Family Matter in a Romantic Relationship?

4. Who would you consider your best friend?

We truly are the company we keep.

Have your man tell you about his best friend, and no, not as a potential suitor. One of the best ways to learn whether this person is worth your time, and quickly, is to learn about the people he surrounds himself with.

They might not be similar—in fact, they might be complete opposites—but they will likely share the same value and belief systems.  If his best friend is a good person, he likely is too.

5. What made you interested in talking to me?

If you are trying to establish an actual connection with someone online, it is important to have mutual interests and the ability to carry on a conversation.

Asking them what made them reach out or respond to you will provide them an opportunity to prove why they feel you could be a good match, beyond just an attraction to your profile picture.

Nick’s View on the Best 5 Online Dating Questions to Ask a Woman

As a man pursuing a woman online, you need to remember that she probably gets plenty of offers. Many of those guys may be insistent in their approach and forget that a relationship is a two-way street.

Remember that the whole point of asking online dating questions is to find a good match both for yourself and for her. Trying to win the game at all costs won’t help you in the long run.

The intimate questions to ask your crush listed below will help you get past the small talk.

1. What is something about you that most people get wrong?

Most people see themselves differently than the rest of the world. Very few of us even go through a full day without feeling like someone else misunderstood us in some way.

If you want to understand how she genuinely sees herself, let her tell you about that hidden side. Each crucial facet of her personality will help guide your decision-making about whether to pursue this further.

If you want to get to know her, this dating question is pure gold.

2. What are your top three bucket list plans?

This question is designed to help you get an idea of what sort of a person she is. Think about it: the things people fantasize about doing reveal their core beliefs.

If she wants to travel and live in different places around the world, she could be an adventurous nomad. If she talks about having children and being able to give back to her community, what would that life look like for you?

Asking about her bucket list will help filter out dating candidates with incompatible life goals.

3. Where would you live if you could be anywhere in the world?

Allowing her mind to roam is a great way to see whether she is actually satisfied with who she is. Having hopes and aspirations are important, but you want to see whether the way she is living her life is consistent with those dreams.

If the place she’d like to live is far from where you both live, is this something she would actually want to pursue? How would you feel about the prospect of leaving your home, job, and other lifestyle trappings?

4. What would you do if you won the lottery?

This is also designed to allow some mental free-play. You want to give her space to be creative and think beyond the day-to-day.

Here are some red flags for an online dating match that you should listen for:

• Dissatisfaction with her current life. If her life after winning the lottery looks entirely different from the one she has now, she feels her life is lacking.
• Selfishness. When most of her responses are about enriching herself and no one else, it suggests she isn’t a caring person.
• Poor mindset. If instead of answering, she talks about how good things never happen to her, that’s bad news.

The best thing you want to hear from this question is about how she would continue building on her current life. Money shouldn’t fundamentally change a person’s life, but can certainly enrich it.

5. How did your last relationship end?

I consider this my favourite deep question to ask a girl. I believe all people should hold themselves accountable for all aspects of their lives. This includes relationships that may not have ended amicably or gracefully.

By allowing her space to talk to you about her last relationship, you are able to judge whether she is rebounding or ready to move on. The worst thing can be entering into a relationship with someone who is still trying to prove something to their former partner. That’s a dead end, and you definitely want to avoid it.

Keep in mind that opening this door is a gateway to high emotions. If you do decide to ask this, be aware that you should also be respectful of whatever she shares. This is personal territory and cuts past the normal dating fluff.

Final Thoughts on Online Dating Questions

They say that looking for love on the internet is a numbers game. If that’s true, then it’s just a matter of swiping right enough times and eventually you’ll get lucky. Anyone who has actually tried this knows that you just wind up jaded with no love in your life.

You can vastly improve your chances of finding a true life partner by asking the right online dating questions. You’ll waste less time and be happier in the end.

The goal with online dating is to find who might fit best in your life, as quickly as possible. Using the questions we’ve listed above for women and men alike will give you the edge you need.