First Date Questions To Ask Women | The Good, The Bad & The Erotic

First Date Questions To Ask Women | The Good, The Bad & The Erotic

Written by dating coach for men Gary Gunn - Founder of Social Attraction

In this article, you will learn the best first date questions to ask women. I will also be teaching you a game to play that allows for some exciting, erotic and engaging dialogue on your first dates.

In this feature, you will discover:

  • Flirty first date questions (for sexual tension)
  • The best first date questions (to connect with women)
  • Questions to never ask on a date (to save embarrassment)

I remember teaching this game to a 35-year-old client of mine in Birmingham, England. What he found on his first dates with women is that they would either end the date early or become disinterested in the conversation. To say that he was frustrated was an understatement. He was putting so much time and effort into getting the dates that when he came to me for advice, he was “taking a break from dating.” I understand that dating can bring even the most confident man down to his knees, especially if he does not know how to navigate the modern dating world. So I stripped back his first date strategy and taught him the game covered in the rest of this article. Aside from revolutionising his first dates, this also had a huge impact on his overall confidence as a man.

When you are frustrated with dating it is always a sign that you need to move in a new direction or to rethink your current strategy.

I hope you enjoy learning and also playing the game.

If you would like to get more dates in your diary, take a look at our client reviews and book onto our next dating confidence course. Watch them on YouTube here: Dating confidence course for men reviews:

Daygame dating course for men to regain confidence

Questions to ask on a first date

The remainder of this article will revolve around a game that I developed seven years ago on one of my dating confidence courses.

The game is known as ‘the questions game.’

It simultaneously offers us a platform for getting to know a girl on a first date, as well as keeping a conversation flowing in any direction that we desire.

The rules of the questions game

To play there are only three rules:

  • “I ask you a question”
  • “You answer truthfully”
  • “Then you ask me a question back, but it can not be the same question”

This is a simple and easy to remember game that will transform your first dates with women.

Introducing the questions game

The best way to introduce this game is to say to a girl:

“Would you like to play a fun game?” The answer to this is almost always a “yes.”

You then simply explain the three rules and get started by asking her some of the questions covered in the rest of this article.

Advice for playing the game

In my opinion, this game should be played in the background of our first date with women.

This means that you ask each other questions but, importantly, you also explore the answers and go off-topic.

You can then return to the game by asking, “Who’s question is it next?” This way you ensure that you never run out of conversation topics with women.

Instant first dates

In my experience, a first date does not need to be organized for some time in the future. I advise my clients to go on instant dates as soon as they are in dialogue with a girl that they like.

This can be:

  • Grabbing a quick coffee together
  • Joining groups on a night out
  • Walking somewhere together

Before we get into the best questions to ask women, it is important to know how to approach and speak to women in the real-world.

This is why I have created the following infographic for you, and you can also read my how to approach a girl at a bar guide.

5 examples of how to approach women in bars and generate conversation

Good first date questions

When you first start playing the questions game it is worthwhile to commence with some emotional-based questions.

Emotional questions are great as they allow us to connect with women over the inner aspects of their personality.

Here are some examples of emotional questions to ask women:

  • “If you could write a book about your life what would you call it and why?”
  • “Which three people living today would you invite to your dinner party and why?”
  • “If you could change lives with anyone in history who would you choose and why?”

The aim of asking these questions is to lift the lid on her outer-self and see behind the scenes. It is impossible to answer any of these questions without illuminating important aspects of your personality.

Moreover, you can also tease a girl by the responses that she gives you to these questions. The infographic below can act as your guide to help you do this or you can read my how to tease a girl article.

11 ways to flirt with women on a first date

Funny first date questions

The funniest first date questions tend to be role-play based questions. These are the types of questions that enable you to put a woman in a difficult or awkward scenario and see how she would cope with the situation.

I have found that these are the more exciting types of questions if you are looking for a fun date.

Examples include:

  • “If you were a man for 24 hours what three things would you do in ranking order?”
  • “A one night stand stays the night at your apartment and you want him to leave in the morning; what do you say?”
  • “You think your boyfriend is having an affair with your neighbour 20 years older than you who lives upstairs, but you have no evidence; what do you do?”

Role-play questions are also a great way to introduce seductive stories. I have covered these in detail as you can see in the infographic below. You can also read my how to create sexual tension article for my step-by-step guide in seductive story-telling and why this works.

Five different ways to create sexual tension with women on a first date

Interesting first date questions

When you are playing the questions game it is essential you ask women a wide variety of questions otherwise the game can become boring.

If you feel like the game is beginning to lose its energy then you can ask some of these questions and then explore her answer in more detail, rather than going straight back to the game.

Examples include:

  • “What was your favourite childhood movie and why?”
  • “If you could travel anywhere in the world where would you choose and why?”
  • “If you could swap places with a celebrity who would you choose and why?”

Each of these questions can generate at least thirty-minutes of conversation with women. I have created the following infographic to help you improve your general conversation skills with women. You can also read my how to carry on a conversation with women featured article.

3 types of intelligence to convey on first dates and in answers to women's questions

Deep first date questions

Dating should be a fun experience shared between two individuals. When two become one for the duration of the date, let me show you how to make that as memorable as possible with some deep questions to ask women:

  • “If you were a philosopher, what would be your one sentence of wisdom?”
  • “What one question would you like to ask your great great grandmother and why?”
  • “If you could change one aspect of our world, what would it be and why?!

These types of questions enable you to form a bond with women, particularly if you know how to echo a woman’s thoughts. My infographic guide below will help you do this. You can also read my how to connect with women article to discover how to demonstrate empathy in more detail.

5 ways to connect with women including questions to ask on a first date

Flirty first date questions

Now we move on to some flirty and erotic questions that you can ask women on a first date. These questions tend to be good to ask women once you know that there is some level of mutual attraction.

Here are some questions that will spice up your first date:

  • “What is your shortest time from meeting a guy to kissing him?”
  • “Demonstrate the top three ways that you flirt with a man that you like.”
  • “The guy you are dating is tired at bedtime, how do you wake him up?”

Below you will find a photo from an event that I hosted focussing on flirting techniques with women. My how to flirt with women 110-minute event is available on YouTube where you can learn some other ways to be playful with women.

Gary Gunn hosting a course on how to flirt with women - useful for any first date

Questions not to ask on a first date

There are certain types of questions that you should not ask women on your first date as they tend to generate a negative response. When playing the questions game it is important to keep the flow towards exciting and energetic topics.

Therefore, it is best to avoid the following:

  • Any questions to do with politics or controversial topics
  • Questions about whether she wants children or her future relationship goals
  • Validation-seeking questions like whether she likes you or finds you attractive

These types of questions are fraught with danger and showcase either immaturity, a lack of emotional intelligence, or needy behaviours which will put women off.

If you would like to learn how to play this game alongside myself and female coaching assistants then visit my live training page and schedule a consultation call.

Modern looking at camera next to three seduction techniques to help on a first date


  • The questions game is a great way of getting to know a girl on a first date
  • There are three rules: “I ask you a question, you answer truthfully and then you ask me a question back, but it cannot be the same question”
  • Mix your questions between emotional, spiritual and erotic as the game progresses
  • Remember to use the game in the background of the date to keep the conversation flowing for the whole date
  • When a girl asks you a good question, make a note of it so you can use it next time you play the questions game

Written by Gary Gunn

Gary Gunn is the bestselling author of An Education In (Online) Dating.

He has hosted over 1000 dating confidence courses in the UK and Europe, as well as over 1,500 courses conducted online.

Moreover, he is the head coach at Social Attraction and leads the team, training and courses.
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