High quality questions to ask on a date that will keep your conversation more interesting, connect both of you faster and earn you more points


Structure of the conversation

Your aim on the first date is to know the person in front of you better and making sure you keep the conversation interesting. To do that, you’ll need to ask the right questions that will keep both of you connected without losing interest in the dialogue.  

Your Introduction

Your introduction matters a lot in such a situation and it’s a crucial thing to consider. The first thing you wanna do is to compliment the person. Look for something you feel is outstanding and point it out because in most cases when a person comes on a date, they ‘dress to kill’ which means you have something to appreciate about them (& there is always something). This alone puts a smile on their face and that’s a plus for you.

Make them feel important and appreciated but remember to be honest; say something they can also concur with. You can point out something outstanding about them, like; has anyone told you, you have blue eyes? have you ever been told you got an amazing smile? you look like (certain celeb’s name). You’re communicating that you’re noticing something special about them & you’re assuming they don’t know it. This makes them feel humbled & special. Those first seconds of introduction create a conducive mood which is a strong foundation for the conversation to follow.

 Important; If you’re a man, don’t wait for her to appreciate you, you should be in control here – it’s not about you anymore; it’s time to look at things from her side. If you’ve heard the saying, ‘Give the fish what it wants and it will give you what you want’ then we have a sealed deal here. Be confident, relaxed and still throughout (be yourself). Don’t cram any introduction vibes you aren’t sure of; just be cool and real because cramming might keep you trapped in your head and you end up messing the whole thing. Let’s now dive into the real thing!

Like I have said before (here); Ladies are like padlocks, they open easily once you have the right key – so it’s not about money, heights or status… it’s just a simple game of question & answer. A game of psychology.

The first question you are going to ask before you settle is; are you okay, comfortable here or would you like us to go somewhere else? You got to understand that the moment she steps into the site, she will be conscious of the place trying to see if she feels comfortable at the place, that question alone settles such anxiety because she feels involved in the choice you made and even if she won’t like the place, she will still feel comfortable since she has accepted it herself.

This makes her think you care about how she feels. Comfy is the goal of the game so make her feel like her safety is a matter of concern to you (But be warned! DO NOT OVERDO IT! It’s boring). If it’s cold ask if she’s feeling cold and if she says ‘yes’ then take your jacket and put it on her shoulders. Of course, it doesn’t have to be cold alone but am sure you get the damn point, do you? (If necessary: hold her hand in your arms beside you as you head to the table, pull the chair for her… society calls it; Being a gentleman.)

I will not talk about the food and other stuff like dress code on your date here because the article is mainly into conversation.

Questions to Ask

The questions I have for you are divided into two sections; section one keeps you both connected and make you comfortable next to each other and section two is to help you know the person very well. Though section one questions are mostly for man to lady while section two is mostly general.

…NOT to do

Don’t ask her, what do you wanna talk about next? Tell me more about yourself, how was your week… Such an approach questions your conversation skills. This implies you’re too general (no content) and you’re giving away your power. A man must not lose his power, take control throughout.

Don’t try to be too serious and professional or start advising her about life. This is not an audition, a job interview or some therapy session. A date is supposed to be fun, a place to feel fresh with someone new. Of course, such things like advice about life are necessary but at least not on the first date.

…to DO

Talk about the person, ask interesting questions about them and keep mentioning their name occasionally in the conversation.  Try to show interest in what they like; makes them feel you’re listening and you care (they feel comfortable and that’s the aim you have here). Talk of a future place you might wanna visit together – for example create a fantasy so they crave to be there. This is to create a network of having a common connected emotion about future.

You might also want to focus on commonalities, things you share in common so as to create the sense of connectedness much stronger. Ask about basics and also remember not to keep following question after another because it will sound monotonous. You can use the questions sparingly like when on the first date, when chatting and also when on the second date.

These questions can only be powerful when applied in the correct way at the correct place and time. Also avoid straight forward questions and you also need to have an answer to every question you ask because chances are that they’re gonna pose them back to you, unless you turn it into a game where you say you’re going to ask first then it’ll come their turn to ask.

So, what’s your ideal date? This question prepares you to know what she’s expecting of you. This is a testing question. Tells you how she defines fun together. It will give you a better idea of how to keep her happy and feeling loved.

How is your weekend like… or; What’s your favorite holiday? The question tells you how she spends her free time and what she is expecting from you in future holidays?

What sort of vacation would you like to take? -Don’t ask if she has had any vocation that year? Talk about travel a lot (exposure) more than movies (idling) because exposure creates better fantasies. This gets you connected faster.

Who is your celebrity crush? If you would date any famous character you know, who’d it be and why? This tells you about her fantasies.

When was the first time you broke a law? …or; First time you disobeyed someone till you got so worried and felt you had messed it all. This triggers her memories that she can share with someone, after she’s moved on. We all want to share those horrifying moments that almost broke us but we got out eventually.

One day of your life you would re-live if you were given a chance …or; What’s your best childhood memory? Reminds them of things they related with a lot in their childhood.

Anything surprisingly happened today? …or; Anything that made your day/week? Don’t ask, ‘how was your day/week’ because this is a closed question. You can also ask of the negative thing about that week or that day, then you get a chance to shine light in her life with some positive perspectives.

Are you working on any personal growth projects like reading self-help books, exercise? This can tell you about her hobbies and how she spends her time. It’s much better and more creative than just asking; ‘what are your hobbies or what do you do?’

If you have a one-way time ticket, where would you go to? Play with her imagination with fantasy questions, like; she has a ticket to go somewhere & she’s never coming back… this triggers her wishes and talk about the beauty of her imaginations.

If you could have one superpower, what would it be and how would you use it? This question is fun because it lets someone share their unlimited moments with you. She can choose flying, speed, being invisible. It indirectly gives you an idea of what she’s looking for in life. You can even create an imaginary scenario where both of you are flying together in that fantasy of hers.

What was the gift you bought someone you love on their birthday? …or What is the best gift you’ve ever received from someone? This gives you great idea for potential future gifts.

Can you let me know as soon as you get home safe?  It makes her feel completely feminine and you masculine because you’re making her safe and you got everything covered. Shows you’re ready to step in to help where she needs you.

When Chatting

When she’s home, try to chat and find out what she found to be so amazing about the date and where she would like to have next date with you. Some of the questions that might apply better when chatting are;

Let’s give each other a random rapper or gangster or some weird name. What would you call me?  You give them yours then try and create jokes out of it for example you diss how yours is much better.

What’s something that you learnt today? Shows you care about what is going on in her life. Such questions connect both of you faster because they increase a bond of friendship between you.

If you could trade life with one person one day, who would it be & what would you want to experience? If she chooses you, the better because it makes her imaginations with you stronger and even if she doesn’t choose you it’s still okay so long as she’s connected to her imaginations and you’re the cause of that.

When was the first time you remember having a sexual thought? This question applies better after you’ve advanced into the third date or you’ve become comfortable with each other so as to create an intimate connection. Asking this on the first date might earn you a ticket to be like ‘other men – they just want sex and leave you’.

If you were told you have only one month to live, what would you do.

Check out part two of this article (here) so, you can get to know questions that will help you know her inner-self better. High quality questions to ask on a date that will help you know if the person in front is the perfect match for you, know their inner-self better and make your conversation more interesting

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