First Date Questions: What to ask and what not to ask!

So, you have got yourself a first date – Congratulations – Now you must arm yourself with first date questions to ask your handsome/beautiful stranger, so that you can relax and enjoy an interesting and flowing conversation, and not have to worry about any awkward silences. But be careful not to make any of these most common first date mistakes!

First Date Questions

“Tell me more about what you do for a living!”

It might seem like an obvious and potentially boring question, depending on what work your date actually does, but finding out more about how they spend most of their time can tell you a lot about the kind of person they are, and what kind of life and relationship you are likely to have with them.

Instead of just asking what they do for a living though, ask them to tell you more about what they do. This is an open-ended question, which means it opens up the opportunity for them to expand and go into detail, rather than shoot a one-liner answer back at you, and stunt the conversation flow. Asking open-ended questions is really important on first dates, when nerves can get the better of people and leave your mind blank. Awkward silences are the worst!

But be careful to know when to intercept the conversation and steer in the direction that interests you most. Otherwise you could end up having to listen to them waffle on about something you know absolutely nothing about, and have no desire to know either!

Tip: Listen carefully to what your date says, and pick up on the details you find most interesting, then dive in to ask further questions relating to the things you are both more likely to have common interests or experiences in. For example, let’s say your date works as a Barista in a coffee shop – you may not be very interested in their job, but you may love coffee, so you can pick up on that detail and find out more about what he knows about coffee. That is a conversation that could then lead anywhere – to talking about food and drinks, different cuisines, countries, travel, holidays…

“How do you spend your free time?”

This is a good one because not only can you find out if you have any common general interests, but you can also find out what kind of person they are – creative, self-motivated, lazy, organized – and you can get a good idea of just how much free time they are likely to have to spend with you!

For example, if someone has a very specific hobby like dancing Tango, which takes up most evenings of the week, are you going to be able to join in and enjoy yourself? Or are their hobbies going to end up becoming an issue between you?

Be careful not to “dump’ too much information at once!

“Dumping” is when you start to talk about something and end up going into far too much detail for a first date. When you do this, you can create a false sense of intimacy before you have even really had the chance to get to know each other. It prevents you from being able to judge whether or not you really get along, because all of a sudden you are the best of friends because you’ve both experienced terrible past relationships, or had awful experiences with a boss.

Don’t allow your date to start dumping on you either. Just because you have asked an open-ended question, it doesn’t mean they should be allowed to “dump”. Often people who are nervous can go to the opposite extreme and become too familiar too quickly.

Also be wary of shooting so many direct questions at your date in order to find out more and more specific things about them. It is much better to peel away layers like an onion and discover things slowly and at a more natural pace.


Feel free to ask about “favorites”.

Asking your date what their favorite food, film, school subject etc. is, can be a fun way to get to know someone – and you get to tell them about your favorite things too! The great thing about asking about “favorites” is that the person is likely to develop a genuine interest in the conversation, because they are talking about all of the things they like the most!

Asking about your date’s “favorites” also gives you the opportunity to find out more about specific things they like. For example, If their favorite food is pizza, you might then ask where they like to go to eat pizza, when the last time they went there was, if there is anywhere they would like to go to eat pizza where they haven’t tried yet – all great set up questions for organizing a second date!

Here are some more ideas:

  • What’s your favorite flavor ice-cream? Or your favorite dessert?
  • What’s your favorite band? Do you have a favorite singer or song?
  • Where’s your favorite place to go to relax?
  • What’s your favorite restaurant? What’s your favorite food?
  • Who is your favorite role model? What influence have they had on you?
  • What is your favorite type of weather? Which country would you like to visit?
  • What’s your favorite book? Who is your favorite author?
  • Do you have a favorite film or film genre?
  • What’s your favorite cocktail? Where do like to drink or go out?
  • What’s your favorite animal? Do you have any pets? Are you a cat or dog person?

Never get into a conversation about religious beliefs!

At least not on the first date! A conversation this heavy on a first date rarely goes well. Unless your religious beliefs are likely to affect the type of relationships you can have, I would steer well clear of this topic of conversation until you know each other better. People have strong emotional reactions to conversations that involve religion. Even politics can be dodgy ground. It is best to stick to lighter topic areas and focus on having fun on your first date! You are just getting to know one another, so give yourselves a chance to get to know the good things first, so that you can deal with more challenging things later.


Ask about their friends and family

Unless you sense that the topic of family might be a prickly one, it is a good idea to ask about friends and family so that you can build up a clearer picture of who your date is and who is most important to them. Asking about friends and family can help you to get to know someone much better. When a person talks about the people they love, it can feel like they are bringing you that little bit closer. It is a good kind of intimate!

“What would you do if you won the lottery?”

Yes – it is quite literally the million-dollar question! Most people have thought about how they would spend their millions if they won, so it’s not like you are putting anyone on the spot. Because it is speculative it can be fun to answer because you don’t have to be too serious. Your date’s answers can also give you some insight into the sort of person they are, and if they are similar to you in any way. You can also just have some fun, dreaming together, while you wait for your starters to arrive…

Remember: The most important thing when you’re on a first date is not to worry about asking the right or wrong questions. It is instead to simply find ways to relax and get to know each other. So, less judgment and more sharing! That is my motto.

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