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20 Must-Know Online Dating Questions To Ask Before Meeting In Person

Dating can be a major time suck. You spend all this time chatting with a guy, only to meet up with him to find out he’s a total dud. Here are 20 Must-Know online dating questions to ask before meeting so this doesn’t keep happening.

online dating questions to ask before meeting dating coach for women

Best Online Dating Questions To Ask A Man Before Meeting For A Date


Before we get into the questions, I have to give you a warning.

As a professional dating coach, I often have women tell me they wish they could just get to the point and ask men the real questions so they wouldn’t have to waste time.

That sounds like a great idea… except-

Men absolutely hate this.

When they can sense they are being interrogated, they want to run.

You don’t want to show your crazy by asking too many nosey questions.

Play it cool, keep it subtle and lighthearted.

These questions are worded in a way that sound playful and fun but the way he answers them will give you a lot of information.

Remember to splice these questions with some back and forth conversation. He doesn’t want to feel like he’s talking to his father-in-law 😀

Related: 8 Reasons Why Online Dating Isn’t Working

Questions To Find Out What He Does For Fun (His Hobbies)

This is a good way to start things out lighthearted.

Ask him questions about his hobbies and what he likes to do for fun.

This is how you find out if he likes to go out and party or if he rather binge-watch something on Netflix.

The answers to these online dating questions might let you know right then and there if he’s your type or not.

1. What’s something you’re really good at doing?

A great one to see what he thinks of himself and what he likes to spend time on.

2. What are you watching on Netflix these days?

See if he’s a TV junkie or if he doesn’t watch much Netflix at all.

3. If you could travel anywhere in the world, where would you go?

A creative question to see how he feels about travel and what type of travel he’s into. Is he an all inclusive-resort or get lost in the forests of Colombia kind of guy?

4. What is your hidden talent?

This is just a fun one to see a unique side of him.

5. If you could spend all day doing something fun, what would you do?

This question will tell you about his go-to source of fun. You’ll see if he’s a homebody who likes to play video games or more adventurous/extroverted and wants to spend time out of the house.

Questions to Find Out His Views On Money

Now that you’ve covered what he likes to do for fun, you can use that as away to get into the juicy online dating questions.

6. So what do you do when you’re not (insert hobby)?

Note: if he just lists more hobbies, you can make it more obvious by just saying “wow that’s awesome, do you even have time to go to work?”. Then he should follow up with what he does and you can ask more questions about that.

7. Do you like what you’re doing now or do you wish you could do something else?

This one is a great way to see if he’s got plans to move up or start a business or if he’s happy where he is.

8. If you won a 100 grand how would spend it?

This is a great dating question to ask because it shows you what he thinks about money. A financially savvy guy might say that he’d buy real estate, or invest it or start a business.

A generous man might say he would give it to charity.

A materialistic will likely just spend it on something like a car or accessories.

9. Where did you go to school?

This is just a generalization, but someone with a graduate degree will usually be more financially stable than someone who didn’t graduate from high school.

This is not always true but it’s a good way to figure a very broad and general sense of his status.

10. Do you think money can buy happiness?

This one is a good look into his financial goals without directly asking.

Related: How To Delete Tinder Permanently and Get On With Your Life

Questions To Determine His Life Purpose

When you’re seeing a new man, you want to know if he has some values and passions that align with yours- or at the very least, passions that you can respect.

Some men don’t have a lot of passion for things and that might be just fine with you. These online dating questions will uncover what he values.

11. What’s something you couldn’t live without?

The answer to this will tell you where his priorities are. If he answers “water” or “air” those don’t count, duh!

12. What are you passionate about?

This question is pretty on the nose but there’s nothing wrong with that in this case. People love to talk about to what makes them tick.

After talking to hundreds of single men, I also find that men who struggle to answer this question do not have a very creative personality. That can be a good thing or not depending on what you’re looking for.

13. If you could change a decision you made in your past what would it be?

This one gives you a sense on how he sees his life. Does he live with regret? Is he stuck in the past or does he want to keep moving forward?

14. What kind of old man will you be?

This is a fun and creative way to see where he sees his life going. Will he be the type to be yelling at the kids to get off his lawn?

Or will he spend 6 months out of the year travelling on his yacht? This question is playful and very revealing.

15. What kind of videos do you watch on YouTube?

When you ask this question to a man, it will seem casual but his answer is very revealing. The kind of stuff he watches on YouTube is a good look into what areas of life he prioritizes and what kind of content he likes to absorb.

Related: How To Find A Husband That Really Loves You

Questions To See If He’ll Be A Good Serious Boyfriend

16. What are your relationship dealbreakers?

This is similar to asking about his pet peeves but it’s tailored towards relationships so you can see if you’re a good fit.

17. What do you wish women knew about men?

This is a fun question that will give you a little inside look into how he sees the opposite sex.

18. Where did you grow up, does your family live closeby?

A good question that can lead you into talking a little more about his family. Generally speaking, men who are close to their family and prioritize that are more likely to be family-oriented boyfriends.

19. What’s something that makes you really angry?

Him making a joke here would be a good thing, it shows that he’s lighthearted and doesn’t think about things that make him really angry.

If he says something that really makes him angry, it can give you a good insight into whether he’s reasonable or not.

20. Whats you’re idea of a good first date?

This is a great one to see if he’s taking things seriously or just wants to wham bam you. It’s also a great way to hint that you might want him to ask you out 😉

Learn More About Finding A High-Quality Man Here.

How To Message A Man On A Dating Apps

Before I leave you, I wanted to give a few bullet points on the best ways to talk to a man on dating apps, here they are:

  • Always keep things lighthearted and fun.
  • Absolutely never ask all of these online dating questions before you have met in person! Choose your battles and save something for the first date.
  • There’s nothing wrong with asking a man out on the first date. If you guys hit it off on the first date, let him be the one to take the lead from there.
  • Clever, witty and flirty should be the tone for all conversations. Deep and serious can fall really flat over text.
  • Avoid sarcasm. It can also fall flat over text.

Related: Best Online Dating Apps For Women

How To Attract A Man That Is High Quality

I hope you found this article helpful but it does you know good if you’re not attracting High-Quality Men.

Find out what High-Quality men look for in a woman, check out my Free Guide “How To Attract Higher-Quality Men”. It’s free!


I hope these online dating questions to ask before meeting in person will help you determine if the man you’re chatting with is dating.

With love from your favourite dating coach,



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Lana Otoya

7 thoughts on “20 Must-Know Online Dating Questions To Ask Before Meeting In Person”

  1. Good post. I think it is very important to ask questions when getting to know someone so that you can know when to move on when things don’t work or when the person may be a good match. Vetting men is very important to do. Especially in today’s times where things seem so challenging when it comes to dating.

  2. I hate to be the Debbie-Downer, but from experience I learned not to get too far into conversation with anyone without doing a background check.
    I asked similar questions to a man I met online in 2020. He answered everything with flying colors. I set up the date. The day we were to go out I came down with a horrible cold (and later I would realize this was a blessing in disguise). So I had to delay our date by two days.
    While I was sick some of the things he told me started drop bother me. But I didn’t cancel the date. I was willing to give him the benefit of the doubt.
    The afternoon before we were to go on the date he texted me that he couldn’t stop thinking about me and needed to know if I felt the same way about him?
    I reminded him I needed to be cautious about my feelings, but I was happy we had met and that I was looking forward to our date.
    That’s when he went into a horrific tantrum and the scolding began.
    I called off the date within the hour. My body was going into post traumatic stress mode from a previous horrific relationship with a psychotically insecure ex-boyfriend . I told him this was too upsetting and I can’t make this work.
    He kept trying to contact me despite blocking him.
    I remembered the free public records search through his county’s Clerk of Courts website. All I needed was a first and last name. So I looked him up.
    I was horrified at the convictions I found.
    Domestic Violence
    Disorderly Conduct
    Restraining Order
    Violation of the Restraining Order
    False Charge of Child Abuse

    I was really upset that the dating site could match me to a convicted domestic abuser. All of his charges were settled to misdemeanors so I think that’s how he wasn’t filtered out.
    A year later I went back to the dating site and asked them “How can you keep me safe from the unsafe people on here?” They didn’t talk about a thorough background check. Instead they told me I should FaceTime with people. I told them this would not have prevented me from being matched and almost going out with a convicted domestic abuser that wasn’t in control of his emotions.
    I don’t know about all of you but I am a 0% match with anybody who’s got a conviction of domestic abuse. I’m not looking forward to introducing my child to a domestic abuser.
    Please do whatever you can to check out someone’s character and background before getting too far into conversation with anyone.

  3. Hi Lana,
    Great article, I am on a European dating site and I am talking to two guys. I am from Scotland, but would be moving to Germany I am chatting with one German and one British guy but the British guy he ask questions he ask me if I prefer romantic or adventure travels? If he arrange for us a trip if I would agree to that? I don’t know what to make out of this. He told me he is a simple romantic man who wants to be loved he ask me what is love to me? He said he knows what our first date is going to be like? Your advice on questions!

    Best Regards

    1. Hey Lina,

      In my professional experience, I would say it’s a little risky to go on a trip with someone you haven’t met yet. I would stay away from this personally but just go with your gut and make sure you stay safe.

      Good luck in life and love!

  4. Dovid Witkowski

    Far too many questions. methinks! I have four basic questions which can be expanded to 5 or to 7.
    1) What books had you read that had a profound effect on your thinking?
    2) What music do you listen to specific pieces or genres, performances etc. (including dance.)?
    3) What movies had a profound effect on your thinking?
    4) Who are your friends in terms of their personal character traits?
    5) Write a few lines about how you view your childhood?
    6) Date, time and place of birth as data for a natal chart.
    7) Do you believe in G-d?
    8)How does this belief manifest itself in the world?
    I strongly suggest that the answers to these questions give an excellent insight into the nature of the respondent.

    1. Thanks for your insight David! I agree that my list is a lot of questions, it’s more about choosing the ones that you feel are the most important to you.

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