20 questions to ask a girl on a date

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  1. #1
    Join Date
    Jul 2006

    20 questions to ask a girl on a date

    20 interesting questions to ask a girl on a date


    This is a field tested list of what to ask a girl to avoid the friend zone, have a fun date, build an emotional connection and ultimately winning her over. And as a bonus, after the list I'll be giving you some tools to come up with your own questions on the fly to once and for all solve any problem with running out of things to say.

    Huge list of questions to ask a girl on a date

    1. If you could live anywhere in the world, where would it be?
    2. What is your biggest fear?
    3. Tell me about something you regret at first but later appreciated doing
    4. What was the best gift you've ever given?
    5. What was the best advice you ever got, but didn't listen to?
    6. How important are your friends to you?
    7. Are you an impatient person?
    8. What did you want to be when you were a kid?
    9. Have you ever ghosted someone?
    10. Have you ever been arrested.
    11. How are you creative?
    12. What are you passionate about?
    13. Do you often remember your dreams?
    14. What is your favorite song?
    15. Who are you closest to, your mother of your father?
    16. What do you hate most about dating?
    17. What's the most annoying thing about you that I should probably now already now
    18. What's your sexiest outfit?
    19. What is the craziest place you had sex?
    20. What are you doing later?

    Suffice to say, you should not only have a good reply to these questions yourself, you should volunteer the reply before she asks. And the last questions is a little test. If she is not doing anything after the date, you would be silly to not move to another place to continue the date, or just take her home. If she talks about being tired or having to get up early, you better ramp up your game buddy, she is bored. But it may change in a heartbeat, so keep going strong, say or do something funny to get her emotions up and rolling, you will see her tiredness disappear into thin air.

    Good topics of conversations
    My favorite serious topics to talk about are music (in the industry), travelling and motorcycles. I will not ask questions per say to get into these topics, instead I will start talking about them passionately and then I will qualify the girl by asking if she likes doing it. I got this line from Keychain once, it goes something like this:

    "I really like people who travel. Sometimes I meet someone who doesn't travel, and have no interest in doing so, and it blows my mind. There is something open-minded and curious about people that have traveled, and I really like that. I can't understand why someone would not want to travel and explore the world - Do you travel?"

    Here you should remember that qualification either happens, or it doesn't. If her reply is short, then you have more work to do in the attraction phase. If she starts talking about how much she likes travelling, or especially how much she would like to, then she is qualifying to you.

    I do something similar with other subjects that are important to me and you can go ahead and directly adapt that sentence to whatever is important to you.

    As for more light topics, I just talk about whatever random stuff comes up. I can literally not think of any examples, it's the lamest of subject and they are really just spur of the moment. Lower your standards for what good communication is, everything goes. Just last night I talked about how girls who doesn't like 3D movies usually also have problems coming. And let's just say that I brought that up at the exact right moment and it ended up being a great succes

    Everything goes, only thing to remember is to shift between normal conversation, fun conversation and more flirty conversation. Don't be a one trick pony. When you talk about a serious subject that is important to her or you, later talk about something that makes you both cry in tears, then you flirt and talk about something sexual and eventually you return to a down to earth subject, then you take the girl, and you, on an emotional journey that's really builds the emotional connection and comfort you need.

    Framework for questions to ask a girl
    As for more tangible questions, I will again go general and give you a form you can use. When girls talk about something, then never say "Cool", instead ask "why do you like X", "how does it make you feel when you do X", "what made you start doing X" or even better, imagine how it must feel to do X, and describe it to her. Example: "Painting, it's something I have never tried, not even in school. But I have sometimes tried drawing something with a pencil, and when I make something that actually resembles what I was trying to express then it's a major feeling of creativity, and freedom almost, a freedom to express something I can't express in words. How does painting make you feel?"

    And by now you may be frustrated and say "Shuck, you haven't suggested anything specific that I can use yet". And you are right. So how do you even find out what to talk about. Well, if the conversation is not flowing, then just start with a standard questions like ""Did anything interesting happen to you today". Hopefully she has something (they always do), and if not, then you tell her about something interesting that happened to you recently.

    If your storytelling is engaging she will bring up something herself, and then you listen for keywords and save them. Look for the nouns, people and places, and build on it. And that brings me to the gist of what I wanted to achieve with this post.

    Actual questions to ask a girl
    So what are some more good stock questions to ask a girl, in order to utilize all of the above, get some keywords and get the conversation flowing? I will start with three, hope you guys have a lot more.

    "I did X this weekend, [talk about how cool it was], how was your last weekend/have you done X recently" (Note, if you didn't do anything cool in the weekend, you should probably start doing cool things)

    "On my way here I saw this travelling add that reminded me so much of my last trip to X that I almost went to the airport instead of here. [talk a little about your travel]. Have you traveled lately? Where/why/why not". (Note, if you haven't traveled lately you should probably start doing it)

    "I was at the gym earlier. 10 minutes on a concept 2 almost killed me. I really want to sin today and indulge in a big fat cup of chocolate or something. What do you like to do when you feel like indulging " (Note: If you're not going to the gym... ok, you get the idea by now)

    Note to the last question. If you asked yourself what a concept 2 is, well, maybe, so will the girl. That's called seeding. If you want to avoid the conversation to die, make sure to not kill it by replying with short or boring answers. Throw out all sorts of words and subjects, and cut threads if you think of something else to talk about, you don't have to logically talk everything to the finish, cutting threads gives both you and her a lot of things to bring up if there's a silence later. Also, asking a question like "how do you like to indulge" gives her a good opportunity to take things in a sexual direction. If she does, for the love of everything that is good and holy, do follow her. But not for too long, just half a minute or so, and then change subject. Don't latch on desperately the first times she talks about something frisky, but know that if she does, you're doing well, and you will get many more chances to take the conversation in the direction you really want.

    What if you run out of things to say?
    If there, after all this, still is a silence, then embrace it. Own it. And then point out the elephant in the room and make it smaller. It's really not a big deal. Say "Well, that's all I got! Quick, think of something to talk about" and smile. It's perfectly normal to not talk all the time, in fact, that is what you do with your friends and lovers: Being completely comfortable with silence. It's actually a good thing, it's a sign of comfort.

    And no matter how the date went, when you get home, write down some of the points where you ran out of things to say, and come up with what you would have said instead. The exercise is called "He said She Said which is a part of the may sound silly, like something an insecure teenager would sit and do, but it's a practice done by man of the best PUAs in the world.

    Hope this was helpful and that you will pitch in with your own conversation tips and strategies.

  2. #2
    Join Date
    Jul 2013

    Thanks for writing this man. I've already tried a lot of the questions, just when meeting girls, and they are really good at sparking up some interesting conversations.

    The he said she said exercise is money!

  3. #3
    Join Date
    Oct 2013

    Thanks for contributing Hurley, this was good stuff.

  4. I like these, many of them could spawn into 30+ minute conversations

  5. #5

    Some questions I've asked:
    Guilty pleasures (favorite guilty pleasure song, guilty pleasure food) and then (depending on her age) who she had on her wall as a teenager.
    Craziest thing you did on a dare
    Worst date you've ever been on
    Girl crush (favorite actress or singer that her friends make fun of her for)?
    First concert

  6. Great tips to read before a date. I always blank

  7. #7

    Quote Originally Posted by Hurley View Post
    Just last night I talked about how girls who doesn't like 3D movies usually also have problems coming
    OMFG, the two most frigid women I've been with didn't like 3D movies and I toyed with that concept in my mind once or twice.

    It might be true!


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