Good Questions to Ask on a First Date to Know Her Better

Valeria Kozlov
6 min readMar 5, 2020

So you are done with the scary, agonizing and tiring part of the love hunt, and found the perfect woman whom you want to meet and get to know more about. And your lucky strike just keeps on rolling as you get her sweet confirmation to that first date.

But do you think that all your effort and hard work ends here? Not really. Think of this date night as the best time for you to decide if the one you are meeting truly will complete your picture of the best kind of love.

You read that right: We don’t adhere to the belief that first dates can’t be more than just jitters and small talks. Because why wait for the second one when you can spend your first time together better by getting to know each other at a deeper and more personal level?

Can’t think of a way to do so? No need to fret. We will share tips to get the best out of your first date conversation. Not only do you take out the awkward feels around each other but you also get to learn the most valuable things about the woman in front of you. A win-win situation if you ask us.

So read on and get ready to take down very important notes.

The first date should give you the first clue if she’s one worth loving. | Photo by Pablo Merchán Montes on Unsplash

1. “What makes you laugh?”

It’s a given that the first date should be fun and maybe a bit funny. | Photo by Jacob Mejicanos on Unsplash

Who wouldn’t want to be in the presence of entertaining people and those who can make them laugh?

If you apply this in the context of dating and romantic relationships, which type of people would you most likely want to be with — the stern ones or those who can put a smile even in the harshest points of life? Obvious choice, right?

Knowing a person’s easy way to unhindered joy is a sweet way to work your way into their heart. Even the science says so!

Simply couple it with sincerity when shooting this question, and we are sure no woman will not appreciate this quirky yet thoughtful question.

2. “What are your deal breakers in a relationship?”

Learning about what ticks her off on your first date is already a good start. | Photo by Joshua Rawson-Harris on Unsplash

When anyone ventures into dating, they are most likely looking for their happy ever after — that is, a relationship for keeps. So asking about your date’s specific dealbreakers is effectively a way for you to learn how to build a healthy relationship for the future. And, trust us, she will admire the effort.

In this same way, you can take note of the things she may not like and avoid them altogether. This question not only shows your respect for her space and her comfort zone, but it also opens up a chance to work out middle grounds if any one of you can’t let go of each other’s considered dealbreaker.

And that’s how you make a very good first impression.

3. “What are the places you never want to visit again?”

Your first date should be memorable — for all the good reasons. | Photo by Alexander McFeron on Unsplash

This question is a unique one to throw at a date, although not unwelcome. Why? Simply because other people usually talk about favorite places, hometowns, dream destinations, etc. Those are well-used ones that require little to no effort to come up with an answer. That’ll end the conversation way too short than you’ve anticipated. Not to mention, asking about your date’s place of birth at this stage of your relationship can come off as creepy.

On the other hand, wanting to know about a place she doesn’t love will intrigue her and stir her into providing little snippets of her life. And, as with the one above, you’ll understand how to play your cards right and know where not to take her next time.

First dates can be unforgettable in a fun way like this.

4. “How do you imagine your retirement will look like?”

Can the first date be a clue for your future? We say yes. | Photo by Tracey Hocking on Unsplash

You might say that this line of thinking is taking things too far. Maybe — if you start listing your very far future plans with her in the picture. But if you stick to the fun, light ones that need not include you in the situation, the question can be an amusing topic to play around.

This question can give you an idea of what she considers as metrics of joy and contentment, whether they may be physical objects or relationships with others. You most probably can get the gist of her dreams from this, and consider if any of these can work well with your own goals.

Listen closely and ask yourself if you can imagine yourself enjoying the same things in your later age and, of course, enjoying them with this person.

5. “Who are the famous people that you look up to?”

There are many essential information you can get on the first date. | Photo by Jenna Anderson on Unsplash

Specific right? That’s the goal — for you to recognize the very person she idolizes and have an idea of her outlook in life. See, when you do not limit the scope she will most likely mention someone she’s close with and you will only have to take her word for it. However, finding inspiration from public profiles will lead to understanding her a lot better.

Does these personalities stand for a cause or are they involved in some shady stuff? Why does she relate to them? Are they known for having a toxic relationship or are they the perfect role model for the love you want to have in the future?

Most people find connection to and even strive to become whomever they are respecting. This question allows you a sneak peek on her morals and psyche, albeit just a bit.

A word of caution though for those who believe that they are already smooth talkers after this dating tip: These questions are only effective and welcome when there is a chance for equal exchange. As much as you are careful not to dominate the conversation, do not allow that your lady date is left spilling her stories all alone. This is a date, not an interview.

Use this list as a guide to a better first date experience and outcome. As we’ve said, learn to play your cards right, genuinely enjoy the night together, and a future happy and healthy relationship could be blooming right in front of you.

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