10 Great Questions for a First Date

Few people are really very good at the art of conversation and it can be difficult to know which questions you should ask on a first date to keep the conversation going.

A first date is not a job interview so avoid questions to do with money, previous relationships and ‘prospects’ (eg where will you be in 5 years). So many dating tips sites suggest you delve into their relationship past but this is not a fun way to get to know someone, first dates should be fun so try to keep it that way and don’t make your date feel uncomfortable.

Also avoid closed questions, where only a yes or no answer is appropriate or where you are obviously looking for a certain answer. An example would be changing the question “do you prefer sun or snow holidays” to “what sort of holiday do you prefer”.

Try to stick to open questions that allow your date to speak freely, believe me you will learn more about them this way.

Here are 10 questions that would be appropriate and fun for a first date:

1. Have you ever read a book or watched a movie that has changed your outlook on life?

2. Where is the best place you have been and why was it the best?

3. What would you do if you won the lottery jackpot?

4. If you could have a superpower what superpower would you choose?

5. How would you like to change your lifestyle if you could?

6. If you could invent a new dish for a restaurant what would it be?

7. What made the worst kiss you’ve ever had the worst?

8. What’s your favourite hobby/activity and why?

9. Are there any causes in life you are passionate about?

10. What’s the funniest joke you’ve ever heard?

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Date Ideas, Dating Advice, Dating Tips

32 Responses to “10 Great Questions for a First Date”

  1. Liz Says:

    These are good ideas, but really they sound like invites to write an essay! Just a bit too rough in my opinion. Those are things that take a lot of thought. I have a good friend who swears by “if you could either have the power of flight or invisibility, which would you choose?” It gets them talking without being overly complicated and stressful on the spot. Seems to work, since this guy has potential mates just hanging all over him!

  2. dave Says:

    4. What are the 5 things you would want to do if you found out you only have a week to live?

    don’t ask this one… it may imply you are going to kill them

  3. Sally Says:

    Good suggestion for a question Liz. Yes the questions may lead to thoughtful answers but I believe they can also lead to fun playful answers.

    Maybe I should write a post on how to avoid dating axe murderers Dave ;)

  4. Anonymous Says:

    These questions are terrible, and awkwardly written. They sound super-generic and all out suck.
    Let me list the ways they suck.
    What’s the funniest joke you’ve ever heard? That this list would be useful.

    You suck.

  5. chris Says:

    7. What made the worst kiss you’ve ever had the worst?

    yeah man, ace! who in the world would want to think about their WORST kiss? how is that going to make it better for you?
    when she thinks of the worst kiss with you in front of her, you’re actually anchoring those thoughts and image to your image. so if you know what’s good for you, don’t.

  6. Colin Says:

    I’m sorry, but I found these questions to be unsettling. They make the person asking them seem more insecure by presenting an image of someone who has sat down and attempted to formalize the structure of a date. This would only make the person being asked more stiff and uncomfortable. This would also make them more unwilling to give the types of answers (presumably the ones in which you learn more about the other person) you want. I believe that the date should not be focused as closely on the style or specific order of questions, but rather on cultivating a relaxed atmosphere. Otherwise, we are all just robots.

  7. Sally Says:

    Hi Chris, if someone tells you that the worst kiss they have ever had was when someone sucked their tongue .. guess what you don’t do if youget the chance to kiss them!!

    Lets be honest Colin, someone that doesn’t have the confidence to just kick back and let the conversation flow is probably going to be a little insecure and may need to formalize the structure of a date. Does it make them sound like robots, perhaps but is that better than a long silence and shuffling of feet .. for some I would suggest yes.

  8. Alien (1 comments.) Says:

    @Chris: Don’t be an AFC. The worst kiss question is really amazing and if delivered correctly, you can neg her well and generate extraordinary attraction sensation in her neurological patterns.
    Play the ‘Game’! Solve the ‘Mystery’ with ‘Style’.
    I know, you still won’t understand it. Take help from Swinggcat or Tyler Durden.

  9. JC Says:

    I disagree with most of the people on here. I think most (not all) of the questions are very good questions for a first date – good, non-assuming icebreakers. That being said, it’s still best ot just make natural conversation if you can.

  10. Jon Says:

    I agree with Colin; these are terrible.

  11. Brittany Says:

    maybe this would be a good one to learn more about a person you’ve been in a relationship with for a while. I mean, a lot of this is stuff I would ask of my boyfriend of a year or so. Things to get to know them better.

  12. Lex Says:

    I actually find these questions to be riveting. The fact that they make somebody think about their answer is actually better in my opinion.

    And, if played right, pre-planned questions can seem pretty spur of the moment and not awkward at all.

  13. Anonymous Says:

    These supposed “Top 10″ conversation topics are horrible. The date and any chances of further dating success will fall apart like a cheap toy at the near mention of any of the suggested advice above. Looks like someone needs to go back to dating school then maybe, just maybe they can begin to write an article giving other people advice on what to say.

  14. Alexander W (1 comments.) Says:

    Hey Sally,

    Don’t sweat the negative feedback here. You’ve done a good job writing some questions that any socially-calibrated individual should be able to lead into in a normal conversation… especially on a date.

    Everyone: Don’t just bring these up out of the blue! One of the skills that we teach at my company (www.theartofcharm.com) is to be able to “bridge” any one conversation topic into another. Learning this skill has enabled me to get out of sticky situations numerous times, and get deeper into conversations I wanted to be in.


  15. Mike Says:

    wow. Come one people. A script for dating isnt necessary or even bull. Just treat the guy or girl like a best bud. Just make fun of other people. i know you want to.

    learn body language because it never lies. :D

  16. Greg Says:

    If someone is feeling a little insecure and nervous, asking #5: [How would you like to change yourself if you could?] isn’t going to exactly boost her (or his) confidence. It seems to me, it would just focus attention on your date’s self-perceived shortcomings.

    First date’s are awkward enough without adding questions more suited to being asked in a therapists office!

  17. kevo Says:

    Came here through stumbleupon, only gave thumbs up for the responses, not the actual content

  18. Adam Says:

    1) You’re all a**holes. If you don’t like the post then navigate away from the webpage.

    2) These are fun questions. I wouldn’t ask most of them on a first date, but definitely good conversation starters.

  19. Sally Says:

    Hi Adam thanks for the support.

    Not my best post I do admit but I was aiming at shy people that find it difficult to chat casually.

    Each to their own.

  20. Jenny in Montana (1 comments.) Says:

    I stumbled here through StumbleUpon.

    The first three questions are excellent and can easily be interjected into a normal first date conversation.

    Questions four and five aren’t exactly first date material. Most people are already very aware of the things about themselves that they’d like to change, and so discussing them would be even more awkward on a first date. Additionally, no one wants to think of what they would do if they knew there were going to leave this world soon, however, a few dates in, this would be an excellent question.

    Questions six through ten are good as well. The idea behind a first date is to come up with not just activities you have in common, but also, thoughts and ideas you have in common as well. How many times have you said yes to a first date based on common enjoyment of an activity, the whole conversation on the first date is centered on that activity, and you find out only after several more dates you really have nothing in common. Personally, I’d have rather discussed a few other areas of interest so that I’m not wasting five more dates.

    Having a few thought provoking questions at your disposal can’t hurt a first date.

  21. Sally Says:

    Hi Jenny

    Thanks for stopping by and leaving an in depth comment.

    You are absolutely right, a first date should be about finding out how much you have in common, both liking skydiving is great but if that is all you have in common it’s not the basis for a good relationship and those extra dates you mentioned could be used finding someone more compatible.

    I have edited questions 4 and 5 to make them more fun and less in-depth. Thanks everyone for the feedback.

  22. ZigZag Says:

    Great list Sally! Anybody hear that thinks, even for a half a second, that Sally meant for these questions to be asked in succession is a complete and utter dolt! I took the post as a guide to fun and thought provoking conversation. Apparently some of you have no social skills whatsoever. (Mike) The mere suggestion that this be a script for a date proves the ineptitude of your conversational skills with humans. Maybe that’s why you choose to make fun of other people on your dates. I’m sure that has worked out really well for you. Hey, if it has, all the power to you. As for me and I’m sure countless others, I like to converse with my date and learn about things we might have in common. Most of these question could be fun and useful in that respect. Plus, if both parties are interested in each other, the chances of more than one of these questions being asked is slim to none. Natural conversation will follow a thought provoking question.

    Then again, all of this is null and void if you pay your date by the hour like I’m sure some of you have to do. You know who you are.

    Many smiles and much love.

  23. ZigZag Says:

    And yes, I know “hear” should be “here”. I’m sure that there are plenty of other mistakes too. But lucky for me…I don’t have to prove myself over the interwebs. So if you want to correct me, don’t bother. I don’t care and unless Stumbleupon brings me back here someday I will never see your holier than thou corrections.

  24. russruggles (1 comments.) Says:

    I think people might be taking these questions a little too literally. They would be useful to weave into a conversation on a date. Ask them all like interview questions? No.
    russruggles´s last blog ..Guys like, girls love My ComLuv Profile

  25. get my girlfriend back (4 comments.) Says:

    Yea I agree taking them literally is not how to look at it. Most of the time when you ask one question to someone new it spins off on tangents that end up starting new conversations about other things. If you can do that with someone on a first date and have a good conversation – and the next thing you know its been 3 hours without seeming like it, you’ll probably get a second date and perhaps a little peck at the end of the night.
    get my girlfriend back´s last blog .. My ComLuv Profile

  26. Tyler Says:

    I’m afraid I have to agree with a bulk of the comments. Most of those comments are just a bit intrusive, and thought provoking for something on the first date. Regardless of peoples own insecurities, a first date is when you get your first impression and the bare minimum of information regarding someones views and/or background. While some topics may lead into other topics, such as asking what made their worst kiss, their worst, it is still something that is going to, in most cases, create an awkward tension. Any person asking about your life-style on the first date is obviously desperate and trying to get as much information on you to make themselves into “what you would like”. These weren’t very well thought-out questions for a first date. However, for maybe more intimate later dates, such as dinner at ones house, or a movie at said same location, these might be plausible.

    Another thing to consider about these questions, is the type of people you are asking them too. People are different, ergo you are going to have to adapt to that within a conversation. If you ask someone about their beliefs, and they happen to be religious, that could lead into a landslide that would just murder any date.

  27. Sally Says:

    Good Lord why are people determined to over-think these questions? Come on people, lighten up and think “enjoying myself”.

    Question: How would you like to change your lifestyle if you could?

    Answer: I’d change careers and be a travel writer. Imagine being paid to trot around the world taking holidays woohoo. What about you?

    Question: What made the worst kiss you’ve ever had the worst?

    Answer: Oh ick, eel tongue, he actually licked my face YUK. Giggle, giggle. Don’t tell me … you thought face licking was sexy hahahahaha.

    Flirtatious, light, can lead to other questions, doesn’t require yes/no answer (leading to an uncomfortable silence), no awkward moments … it’s not rocket science people!!

  28. Carrie from getexbackproductreviews (1 comments.) Says:

    First dates can be pretty awkward. I think it’s a good idea to have some things to bring up to talk about. But I would lean toward more humorous things. If you can find out if they like movies, for example, then it’s easy to find movies to talk about. I think rather than worry about having an agenda of questions, just try to observe the other person and be yourself as much as possible – don’t try to sell the other person on someone who isn’t really you cause it’ll never go anywhere.

  29. Jake McMurphy (1 comments.) Says:

    I love the question about the super-hero. If someone asked me that I’d probably fall in love with them on the spot! I think that any question that can really open up conversation is really great. Questions that make the other person think but not feel like you’re prying into their personal business are the best kinds of questions.
    Jake McMurphy´s last blog ..Ways To Attract Women- Myth BustingMy ComLuv Profile

  30. Dateomatic (1 comments.) Says:

    You make a few simple icebreaker suggestions as an idea to help with those moments of silence and you get the Spanish Inquisition (“nobody expects the Spanish Inquisition”). Just take what you need and suites you and leave the rest, or at least let the post provoke you into thinking of your own.

    Take it for what it is. Sally’s great post simply suggest that people who are not naturally chatty might like to have some conversation provoking questions in their arsenal.

    It should go without saying, you don’t bother asking millionars what they would do with a lottery win! (or maybe you would if you wanted to know how philanthropic they are) etc.

    Keep it light, have fun and a few conversation provoking questions can be useful – unless you British it’s easy for us Brits we can talk about the weather for weeks!
    Dateomatic´s last blog ..Bike2 DateMy ComLuv Profile

  31. Craig (1 comments.) Says:

    Hey, these are good tips and I think you are getting at the core of it. The bottom line is to keep things fun, yet really get to know the other person. To avoid having the questions come across as canned, you can ease into them. For example, “Did you get your good looks from your mom?” can help you shift the conversation to a girl’s background. “So, are you going to watch the game this weekend, or are you one of those people who’d rather read a book?” is a more casual way to ask about hobbies and interests. As long as you have a playful attitude you can ease into just about any question; just don’t come across as being direct or humorless or you’ll freak out your date. Be subtle, have fun, and transition to highly personal subjects slowly.
    Craig´s last blog ..Tips for great conversationMy ComLuv Profile


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