102 Must-Ask Online Dating Questions to Connect Online

In this article you will find the most promising 102 online dating questions for her.

With them you get to know your matches faster and better.

Spoiler: You will not find any question in this list that makes you seem uncreative or overly interested.

I have filtered out the most challenging, humorous, teasing, profound and spicy questions so that you can copy-paste them easily.

Minimum effort – maximum success.

Underneath, I’ll show you:

  • 5 online dating flirty questions that you seduce her with at the same time
  • From online dating to WhatsApp: How to get her number easily
  • 36 scientific great online dating questions to make a woman fall in love with you
  • The most miserable ice breaker questions you can ask (you’ll scare her away with these…)
  • How you get her to go on a date with you
  • And many more online dating questions to ask before meeting…

By the way, have you seen my free Transformation Kit?

You'll get my best stuff absolutely free: 12 Opening lines that actually work, my 5 best texting tips (including copy-paste lines for Tinder), and the Friendzone Houdini. Download the Transformation Kit here.

Tip #1: Starter online dating questions

We’re jumping right into it, bro.

You and I both know you don’t want to be like the rest of men.

Because there’s too much blandness in online dating land… There are too many mediocre dudes with mediocre questions.

That’s why we will simply do it differently.

More extreme, a little crazier and more original.

You can ask your match the following:

  1. What are you most proud of?
  2. What’s the most extraordinary thing about you?
  3. What was the craziest dream you’ve had lately?
  4. What’s the strangest place you’ve ever had sex?
  5. What was your craziest vacation experience?
  6. What’s the furthest country you have ever travelled to?
  7. What’s the most embarrassing entry I would find about you if I type your name into Google?
  8. What’s the worst date you’ve been on?
  9. What’s the strangest thing you’ve ever said to anyone?
  10. What do you think is the best question to ask someone?

Pro tip:

Do not copy arbitrarily any questions. Look at the profile of your match and choose questions that match her.

Also, choose mainly the questions from the list that you think are appropriate.

However, be open to also try ones, which seem more risky to you. This way you’ll develop a better gut feeling for women.

>> Signs of a Healthy Relationship: 11 Telling Questions.

Tip #2: 27 of the best online dating questions to get to know her

Are you ready for 27 questions that you can send to ANY match without hesitation?


Among other things I have 23 further online dating Lines, which I don’t share with every Average Andy who walks by.

They are 23 conversation jewels that I would like to give only to the most motivated men who are REALLY interested in improving their love life.

Get them right here for free.

You’re welcome.

Anyway, let’s continue with the 27 questions mentioned:

  1. What was the last song you heard?
  2. What do you think about social media?
  3. If you were a character in a book – how would the author describe you?
  4. What’s your earliest memory?
  5. What’s the most ridiculous rule that you have set for yourself and that you stick to?
  6. What are you afraid of?
  7. If you could change one thing on this planet that not only has advantages for you – what would it be?
  8. What have oyu never done, but would you like to do?
  9. When you kiss someone – do you prefer the upper or lower lip?
  10. North Pole or South Pole?
  11. What does an ordinary Sunday look like for you?
  12. Which dream do you still remember vividly?
  13. What are you most insecure about in your life?
  14. What’s something you don’t dare to do but would like to do once?
  15. In which things do you behave more masculine and in which more feminine?
  16. What would the perfect room look like where you would like to spend your free time?
  17. What do you think is the strangest question you can ask your date?
  18. What do you and your family members have in common?
  19. Would you prefer certain family members over your parents?
  20. Would you rather have a million dollars given directly to your hands or would you be patient enough to wait 30 days for a penny, but from then on it doubles every day?
  21. Which word describes you best?
  22. What do you do when you’re not XYZ? [Insert an activity she mentioned in her description or conversation]
  23. If you had to describe your life in three words, what would they be?
  24. Have you ever made a list of things you want to do before you die? [If she answers yes] What’s the first item on your list?
  25. Would you rather sit on someone’s lap or would you rather let someone sit on your lap?
  26. Sunlight or moonlight?
  27. What would you do if you were locked in IKEA for a night?

Choose questions you like best.

Women notice it when you suddenly ask questions that don’t really suit you or appeared too forced.

For example, I would use question No 12 rather rarely.

Because it works badly?


Because I am less interested in the subject. However, if you like to talk about social media and want to know her opinion about it, then: Go for it!

Rule of thumb:

Use mostly questions that you would ask someone in real life. You’re interested in whether she prefers dogs or cats? Go ahead.

What – animals haven’t played an important role in your life so far? Then pick another question.

Tip #3: 5 original online dating questions to seduce her at the same time

TextGod Louis and I made a video a few years ago by doing the following.

First, we approached women and asked them for advice on how to get a woman’s number.

Then we returned to them and used the exact line they had given us.

How the women reacted to this? See for yourself (some women speak English by the way):


Even a reputable news portal reported on us.

The headline?

‘Prehistoric’ seduction tricks work’

And so it is.

It works. And it’s extraordinarily fun to watch.

And you know what the best part of this ‘trick’ is?

You can also use it for your matches.

So, just ask your matches for advice on how they would ask a woman on Tinder – for example, for her number – and then use the same phrase.

See also the following questions:

  1. What kind of man would you fall in love with right away?
  2. You know, I have a friend who’s more like a sister to me. However, she is now in love with me, but I only want to be friends with her. How am I supposed to handle this?
  3. Which characteristic of a man are most likely to melt you?
  4. Imagine someone cheated on you. However, he does it responsibly and uses a condom. What kind of flowers would he have to buy you in order for you to forgive him?
  5. I heard today that a good buddy of mine with whom I used to play football is gay. They say he’s even in love with me. But I like women and I don’t want to hurt him or destroy our friendship. What would you do in my shoes?

Look at question number 38. Questions like these are fascinating. An answer to this question will give you good insights into the female brain. You can immediately benefit from the information you gain from her on this.

>> Seducing a Woman Over Text – 7 Examples of Building Tension.

Or question number 39: With this question you signalize to her simultaneously that you have several women who adore you. That automatically makes you more interesting. After all, other women also seem to find something attractive about you.

Or question number 41. With this question you slightly provoke your chosen one and seem more like a man for one night.

Tip #4: 10 effective online dating questions to get to know her

You want to ask her some more questions? Then open your eyes wide. Here are 10 real pearls:

  1. Immortality or invisibility?
  2. Sunrise or sunset?
  3. Peanut butter with or without pieces?
  4. Are you more of a morning person or a night person?
  5. Have you ever bungee jumped before?
  6. Would you rather take a trip around the world or rather settle on a desert island?
  7. Dogs or cats?
  8. What was the last movie that made you cry?
  9. Who’s your biggest role model?
  10. Would you rather be a famous movie star or would you rather date a famous movie star?

Tip #5: 7 creative online dating questions

Would you like to know which questions your absolute favorite dating coaches prefer to use?

Then this is your lucky day, amigo.

Here are 7 of our favorite questions:

  1. What was the biggest age difference between you and a man you’ve kissed so far?
  2. Imagine you meet this man… the chemistry is amazing between you. You kiss. You have several phenomenal dates… until you hit a hot spot: You want to sleep together. But then, when you get in bed, he suddenly confesses: ‘I must tell something, baby… I’m a transsexual.’ What would you do?
  3. If you could spend a weekend in any place in the world – which place would you choose?
  4. Can you name three similarities between the Sahara and the South Pole? [Excellent question to find out her intelligence or creativity]
  5. What three things do you have a passion for?
  6. What would you do if you met your dream man? How would you seduce him?
  7. When did you have your first kiss?

Tip #6: Always have ‘Would you rather…?’ questions ready: How? With this tool

Would you like to have a list of spicy questions available 24 days a day, 7 hours a week to spice up your conversations?

Or at least get more inspiration?

Tell no more.

On the Instagram page of Dilemmarama, you’ll find hundreds of tricky ‘Would you rather…?’ questions that you can easily slip into your conversations.

What would you choose here?

I’d rather walk around for a year with my shoes knotted together.

But how would your chosen one decide? Find out by asking her.

>> How to Kiss Properly – from Novice to Master in 15 Tips.

Tip #7: Miserable online dating questions that you shouldn’t use

‘The most frequently asked questions are the most miserable questions.’ – Abraham Lincoln (169% historically correct)

And here I agree with old Abe’.

They’re too:

  • Ordinary
  • Boring
  • Predictable

But nevertheless, these questions are used inflationary by uncreative men as opening messages:

  • Hey, how is it going?
  • Where are you from?
  • What do you do for a living?
  • Did you have a nice weekend?
  • Are you also already looking forward to the weekend?
  • How are you doing?

Listen, bro.

If you really want to achieve success in your love life, then delete these questions from your memory.

Poor originality can be punished mercilessly. Women can be cold as ice about that. Rightly so – because with the questions in this article it’s surprisingly easy to stand out from average Joe…

Tip #8: Online dating questions to make her fall in love with you

Did you know that there are scientifically based questions with which two complete strangers can fall in love with each other in a very short time?

As part of his research on falling in love, Arthur Aaron, former professor of psychology at the University of New York in Stony Brook, has filtered out 36 questions that can do just that.

The questionnaire is perfect for dating.

However, it is also fantastic for online dating conversations.

For this purpose, I have divided the 36 questions into three parts, so that you know exactly at what time of your conversation, you can use which block of the questionnaire.

Pro tip: If you want to experience the same intense experience as the subjects from Aaron’s study, then arrange the questionnaire as follows…

  • Step #1: Invite a lady on a date
  • Step #2: During the date, ask her ‘Hey, you know what?… You seem like a brave woman… are you?’ and wait for her answer
  • Step #3: Challenge her ‘I read an article the other day about a crazy study in which complete strangers fell in love in a very short time using a special questionnaire… Do you think you have the guts to go through it with me?’.
  • Step #4: Go through the questionnaire (which I have divided into three blocks below) chronologically
  • Step #5: At the end of the last question, participants were asked to look into each other’s eyes for four minutes without interruption and without saying any word. So, if you want to reenact the experiment in a very precise way, then this step is essential.

Part 1 – Initial questions to get to know each other better

If the conversation is still young, you can ask your match these questions.

  1. Given the choice of anyone in the world, whom would you want as a dinner guest?
  2. Would you like to be famous? In what way?
  3. Before making a telephone call, do you ever rehearse what you are going to say? Why?
  4. What would constitute a “perfect” day for you?
  5. When did you last sing to yourself? To someone else?
  6. If you were able to live to the age of 90 and retain either the mind or body of a 30-year-old for the last 60 years of your life, which would you want?
  7. Do you have a secret hunch about how you will die?
  8. Name three things you and your partner appear to have in common.
  9. For what in your life do you feel most grateful?
  10. If you could change anything about the way you were raised, what would it be?
  11. Take four minutes and tell your partner your life story in as much detail as possible.
  12. If you could wake up tomorrow having gained anyone quality or ability, what would it be?

Part 2 – Questions with depth

To create a deeper connection to your match, you can ask her these questions.

They are great if you have already exchanged numbers and are continuing to write on WhatsApp/ Telegram/ iMessage.

(By the way, you will learn how to ask her for her number in an attractive way in the next part of this article).

  1. If a crystal ball could tell you the truth about yourself, your life, the future or anything else, what would you want to know?
  2. Is there something that you’ve dreamed of doing for a long time? Why haven’t you done it?
  3. What’s the greatest accomplishment of your life?
  4. What do you value most in a friendship?
  5. What’s your most treasured memory?
  6. What’s your most terrible memory?
  7. If you knew that in one year you would die suddenly, would you change anything about the way you are now living? Why?
  8. What does friendship mean to you?
  9. What roles do love and affection play in your life?
  10. Alternate sharing something you consider a positive characteristic of your partner. Share a total of five items.
  11. How close and warm is your family? Do you feel your childhood was happier than most other people’s?
  12. How do you feel about your relationship with your mother?

Part 3 – Questions to create a Bonnie and Clyde feeling

The following questions are suitable if you have already met on a date and you want to give your connection to her the certain ‘us against the rest of the world’ character.

(By the way, in this article I show you how you win her for a date in simple steps).

  1. Make three true “we” statements each. For instance, “We are both in this room feeling … “
  2. Complete this sentence: “I wish I had someone with whom I could share … “
  3. If you were going to become a close friend with your partner, please share what would be important for him or her to know.
  4. Tell your partner what you like about them; be very honest this time, saying things that you might not say to someone you’ve just met.
  5. Share with your partner an embarrassing moment in your life.
  6. When did you last cry in front of another person? By yourself?
  7. Tell your partner something that you like about them already.
  8. What, if anything, is too serious to be joked about?
  9. If you were to die this evening with no opportunity to communicate with anyone, what would you most regret not having told someone? Why haven’t you told them yet?
  10. Your house, containing everything you own, catches fire. After saving your loved ones and pets, you have time to safely make a final dash to save anyone item. What would it be? Why?
  11. Of all the people in your family, whose death would you find most disturbing? Why?
  12. Share a personal problem and ask your partner’s advice on how he or she might handle it. Also, ask your partner to reflect back to you how you seem to be feeling about the problem you have chosen.

Tip #9: Get her number? This is how you do it…

As you may have guessed, there are several ways to get a number.

While some AttractionGym coaches first exchange numbers and then set up a date

… there are just as many coaches who first set up a date and then exchange numbers.

Both ways work bueno.

In this article, however, I will show you the second method.

To mentally prepare her for a date, you can send the following questions:

  1. What’s your perfect date?
  2. A handshake, three cheek kisses or a hug at the beginning of a date?
  3. How do you prepare for dates?
  4. What’s your favorite spot in XY? [Name of city you want to meet her in]
  5. Where would you take me on a date?

This way your conversation goes straight to a date.

While you do this, you want to play with her answers to your questions.

A handshake, three cheek kisses or a hug at the beginning of a date?

Anything but a handshake. This is way too businesslike.

Ha-ha, yeah. It’s like having an affair with your boss. A hug’s the way to go.

What you can also do is shoot a ‘Would you rather…?’ question into her inbox.

  1. Coffee or tea when we date?
  2. Pool or bowling for our super romantic first date?

Pro tip:

If you want to suggest a date, give your match two options of when you could meet her. This way you have 69% more chance of success (true story).


More undeniable lines you can use online (and offline)

These were 102 online dating questions that will inject a good portion of fun into your conversations.

I wish you spicy talks and even spicier dates, my dear companion.

To get more out this article, I recommend you download my free Transformation Kit.

Filled with my best advice for both online and offline dating.

See you there.

Your bro,
Dan de Ram

Stop awkward conversations
and painful rejections

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  • 12 Opening Lines that Actually Work
  • 5 Date Generating Texting Tips (Plus Copy-Paste Lines for Tinder)
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