20 Fun Questions to Ask on a First Date for the Best Conversation

First dates are nerve-racking! Make sure to arm yourself with these perfect questions to ask on a first date to be sure the conversation will flow.

Do you know what you should be talking about on a first date? Sometimes it’s hard to know what questions to ask on a first date, and what’s good for the conversation or one that will bore them to death. Or make them think you are crazy!

Really, it is all about reading the other person. You want to find out as much about them as possible without asking them for their medical history. You want to be able to tell if their interests, hopes for the future, and sense of humor are compatible with yours, and most of all, let’s face it, you just don’t want there to be any awkward silences!

[Read: 15 things you must do on a first date to make sure your date falls for you]

First date conversations not interrogations

First dates, however, should be focused on fun, and getting to know one another naturally. While you might be dying to know all about their ex, or how much money they earn, these type of overly personal questions should perhaps be left until you get to know your date a little better.

If they come up in the natural flow of things, that’s fine. But maybe you should be asking yourself whether you want to be with someone who talks about their ex-partner and how much they earn on the first date anyway! [Read: 14 signs you are ruining your first date unintentionally]

No one wants to be interrogated or feel like they don’t have room to eat/drink/breathe before the next round of questions is fired at them. So go easy, give them a chance to answer, and use these 20 questions to ask on a first date to have a fun-filled evening where you can get to know your date, and find out for sure whether they are worth a second one.

Step one: The initial meeting

Once you have greeted each other, sat down, ordered food and drinks, or whatever it is you need to do to get the date started, you then need to get the conversation going. Keep things simple at this stage. No one is going to judge you for asking pretty standard questions at this point, you don’t have to be witty or unusual, just find out the basics. [Read: 20 ways to perfect your first date conversation]

Some solid questions to start you off are…

#1 What do you do for a living? Followed up with, how long have you been doing it? And, do you enjoy it? This will give them a chance to talk about their job, and you find out a little bit more about whether or not their career is important to them and why. [Read: 5 perfect questions to ask on a date]

#2 Where are you from originally? It’s nice to find out a little about someone’s background. They may have grown up somewhere exotic or interesting which leads to further questions such as, “What was it like to grow up there?”

#3 Next find out where they’ve studied and what subjects they took. This gives you clues about their interests and what kind of things they know about.

A good date will ask all these questions back to you, so this should keep you going until the drinks arrive!

Hopefully by now you both have relaxed a little, and you’ll already be able to tell if your date is an easygoing, talkative person *fingers crossed*. Now that all the pleasantries are out of the way it’s a good idea to get a few more details out of them and find out more about what makes them tick, what they love to do in their spare time, and any pet peeves or particular passions they might have. [Read: How to not be awkward – A guide for the quirky ones]

Going deeper with the questions to ask on a first date

#4 What do you like to do outside of work? Hopefully they will reveal some cool and interesting hobbies that you can chat about for a while.

#5 What kind of TV/movies/music are you into? This makes or breaks it for some people, particularly when it comes to music. But it’s good to keep an open mind. However, if they are a diehard Metalhead, and you are more of a Taylor Swift fan, it might not be a match made in heaven.

#6 Where have you traveled? This is a really interesting question to ask someone as talking about traveling leads to loads of interesting side conversations like realizing you have been to the same places, or revealing some crazy things you got up to when you were there. Also ask them if they have any future traveling plans *but try not to make it sound too much like you are vying for an invite*. [Read: 18 things you HAVE to avoid doing on a first date]

#7 Have you read any good books recently? Of course, if you are not a book lover yourself you might want to avoid this question. However, if you are an avid reader, this can start an interesting and lively conversation as you share the literature you love.

More personal questions that are first date safe!

Hopefully by now you and your date are getting along like a house on fire. So, if the mood feels right, now is the time to get a little more personal and have some fun with it too!

#8 Do you like pets? What is your favorite animal? Finding out if someone is cat crazy or goes doolally for dogs reveals a lot about them, and if you are passionate about your four-legged friends you’ll want to check that they are too, from the outset. [Read: 18 signs your date really likes you on the first date]

#9 What’s your death row meal? Okay, so if you don’t want to sound too morbid you could just ask, if you could only eat one thing for the rest of your life, what would it be? Chatting about your food likes and dislikes is really fun, plus it’s valuable knowledge to keep hold of in case you progress to cooking dinner for your date in the future!

#10 If you won the lottery, what would you do with the money? This is a fun conversation starter and helps you find out if your date is a big spender or has an entrepreneurial streak.

#11 What is the scariest/most embarrassing/strangest thing that has ever happened to you? Again this is a great way to start a funny/silly conversation, and gently mocking your date is an easy way to start flirting with them too! [Read: 15 obvious flirting signs between a guy and a girl]

#12 Do you have any siblings? Do you get on? Do you get on with your parents? Finding out whether someone has a good, close family life can be pretty important for some people. If it is to you, then ask away.

#13 What would your super power be? This fun question really lets your imaginations run wild.

#14 Who is your celebrity crush? This is another great opener to steer the conversation to a flirtier tone. When they ask you, say who it is, and then tell them they look a bit like them—a sweet compliment, without being too forward. [Read: 18 signs your date clearly likes you on your first date]

#15 Do you prefer a night out or a night in? If you love nothing more then dancing until the sun comes up and your date prefers a cup of tea and a cozy night in, you may need to rethink this one!

Ready for a second date?

At the end of your date there are a few cunning questions to ask to get a second one firmly secured there and then.

#16 Fancy a nightcap elsewhere? Why let the date end now? If they are interested and having a good time they’ll say yes, unless they have a very good excuse! [Read: Why there’s nothing wrong with having sex on the first date]

#17 What are you up to for the rest of the weekend? This is a casual hint that you might be up for another date pronto!

#18 Are you busy next week? Finding out when they are free without being too pushy is a great prompt to get them to suggest a second date. [Read: The texting and follow up guide after a great first date]

And if it’s gone REALLY well…

#19 Fancy coming in for a coffee?

# 20 Wanna come home with me?!

[Read: First date moves that will 100% guarantee a second date]

These 20 questions to ask on a first date are perfect to keep the conversation going. And hopefully they’ll be enough to keep your date excited, so whether the date is a hit or a flop, at least the conversation won’t be too painful!