Great Questions for a First Date

Most men do the standard interview questions on a date: where are you from, what do you do, what hobbies do you have, favourite film, what do you read, do you have brothers and sisters.The fact is, the average beautiful woman has been on hundreds of first dates and has been approached by guys in bars and clubs thousands of times. She doesn’t want to answer these questions over and over. How do you stand out and make a killer first impression? Ask great questions!

Great questions fall into a number of categories. They all share a few traits:

  • They are original.
  • They bring out an old memory.
  • They bring out a positive emotion.
  • They challenge her.

Let’s get onto the questions:

1. Did you have an Imaginary friend when you were young?

2. Do you remember your first day at school?

This is a question that brings out strong emotions because it is something that they probably haven’t talked about for a long time, but that has strong emotions attached to it.

3. If you could wake up tomorrow anywhere in the world, where would it be?

This is another good question and replaces boring questions on this subject such as “do you like travel?” and “did you go on holiday this year”. Get her to describe the place vividly until she feels like she is there!

4. Are your friends mostly men or women?

This tells you something about their character and also gets them talking about people they care about and their friends.

5. What’s the one thing you can’t say no to?

This is a good way to find out something they really enjoy, it could be chocolate, it could be fresh orange juice. It should make their eyes light up. You can then describe how good it is to eat that chocolate or drink that fresh orange juice and watch how you can lead them into a desiring state.

6. What talents do you have that would surprise me?

This is a great question, and is a challenge. Early on in an interaction, they won’t feel any need to answer challenging questions. By the rapport stage, they will feel some pressure to respond to a question like this to prove themselves to you. Remember that she is likely to ask the same back to you, so have
something ready.

7. Have you been in love?

Focus on the time when they were actually in love, don’t ask what happened – this would focus on the break-up! You will make her want those feelings again, and since she is with a cool guy, she’ll probably be imagining them with you. This is a great one, for a number of reasons: First, it brings out the emotion and memories connected with love. Second, it gets onto the subject of relationships and so gets her to easily start to imagine a relationship with you.

Throw out some of these great questions and you’ll have the woman thinking you are the most interesting person she ever met. Not only that but you’ll have a deep connection, something you can never get with “so… you have any hobbies?”

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Master Trainer, CEO

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  1. Michael mcewen says

    Nice article. Only flaw is the idea that most beautiful women have been on hundreds of first dates. Let me break this down for you:

    1) beautiful women do not go on more dates than less attractive women
    2) the 9s and 10s get hit on less than the 7s and 8s
    3) yes. If you are on a date and she has attraction for you she does want to answer them.

    • James Francis says

      I could not agree with you more. I wonder if its because guys are more insecure about talking to the tens? Or is it that the tens kinda know they are tens and are more selective. Maybe a combination. I knew a ten who wouldn’t go out with anyone. Till she found her “perfect match” and two months later they were engaged. haha

      • PUA Training says

        Every girl is different, but for the most part 9’s and 10’s are and can be highly selective because they are so in demand by a lot of guys. Having said that, they are usually the most insecure, which is why they don’t go for guys that could be hotter than them. Gives us normal guys a chance!

  2. I like to ask chicks… How do you feel about ass licking? answer… Because I dont care how many drinks you buy me, I'm not gonna lick your ass!

    Then I tell a story about one of my dirty asslicking friends.

    It is pretty funny… Especially when the girl expects cookie cutter questions because you just met her

  3. The Bloodhound says

    "The complete book of questions" by Garry Poole.

    1001 great conversation starters.

    Memorize a few of them before you go out or scribble them down.

    Works for me!

  4. Great! They're all in your excellent book too.

  5. Good questions, but I'd always try to stay clear of making it sound like you're conducting a survey/interview/test. You might want to add why you're asking it, you can give your answer to the question to share the dialogue. Thus if you ask about her first day at school, she's likely to want to know about yours, make sure you throw something comical in there.

    I'm currently living in Asia and I find that a lot of girls here don't have fond memories of their childhood or they don't wish to speak about it unlike their western counterparts. I, myself, only ever get asked the same old boring questions from ladies like what do I do, how long have I lived here, why do I live here. They're just trying to check my financial status and my stability, if they want to date me is it likely that I'll just leave the country in a few months? haha.

    I think along with the questions, you might want to use some personality readings such as The Cube or the Ring routine, do the 5 questions game to (I've used them often and I've hardly ever had them fail) or do some mind reading tricks (the number games), they just make the conversation a lot more interesting, they enjoy it, because which girl doesn't like to know more about herself.

  6. Splendid article!!
    I had trouble with conversation and asking questions
    and this seems really logical
    but I have a question what
    other elements a challeging questions includes?
    and right now I have trouble with being dominant
    like many guys are trying to spit game with the same girl I want to spit game to and like i back down
    and I am tired of doing that
    what can I do?

  7. The pinciples mentioned rock: original, bring an old memory, be uplifting, challenging.

    I remember being on a date and I asked the girl a question to which she clicked and gave me a really long, and frankly boring and naive, reply. This surprised me and I kinda went off her, but i realise now I had found a way to open her up. I've included the question in the following list.

    Here are a few more questions folks:
    – What are the three most embarassing things that have happenned to you?
    – What was the best day in your life?
    – What is your favourite position [use this one with care!]

    Well, that's enuff. Cant give away all my secrets… ;)

  8. haha… wow, wish i would have had some of these in mind a week ago… had a date with an hb and the usual word vomit cookie cutter bullshit came out… needless to say, not to sure about a second date. Anyways, good stuff… Have you guys ever heard of socratic conversation?

  9. These are really good.

  10. this one really rocks…. i would love to have another batch of these questions…. ^^

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