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Great First Date Questions


Richard La Ruina, author of The Natural Art of Seduction, sent in these great questions to ask a girl on a first date. This is a good article for those of you sick of the same old first date small talk.

First Date Conversation

by Richard La Ruina

girlbaddate650Most men do the standard interview questions on a date: where are you from, what do you do, what hobbies do you have, favorite 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?”


About Bobby Rio

I'm Bobby Rio, one of the founders of TSB. I tend to write about what is on my mind so you'll find a mix of self development, social dynamics and dating articles/experiences.  For a collection of some of my favorite articles check them out.

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  1. ScottUA

    January 2, 2008 at 11:17 am

    Like these questions…these would be really useful for making an emotional connection to a girl. Richard, thanks for providing these!

    ScottUA’s last blog post..Art of Cold Reading- Best PUA Techniques For Cold Reading Women

  2. ScottUA

    January 2, 2008 at 11:19 am

    Forgot to add…these would also be great during qualification/comfort building when you first initiate a conversation.

    ScottUA’s last blog post..Art of Cold Reading- Best PUA Techniques For Cold Reading Women

  3. mike

    January 2, 2008 at 1:08 pm

    those are good. thx

    Recently I realized that good conversation skills are absolutely necessary, and lacking in my toolbox.

    Those above mentioned questions are cool ways to get her talking and getting emotional…and then PUA must follow with interesting convo, which until now, I didn’t know how to.

    Anyone have tips, tricks, or stuff to read regarding this subject?? I’ve been checking on this website and the articles are good but I’m looking for more stuff. (The MtV guys are good at teaching this – I just got their new DVD and it’s VERY GOOD!)

  4. teddy bear

    January 2, 2008 at 1:21 pm

    i think number 5 is awesome and if your into NLP number 7 can work wonders if you anchor those feelings but 5 you can really use to your advantage
    how about
    8. If you could be any Super hero who would you be and why?
    i’ve used this one alot and you can really dig deep into this question and learn alot

  5. Rubix

    January 2, 2008 at 2:03 pm

    I think #2 is the best. Any question or statement that arouses *Hopfully* postive feelings and memories in an woman is the best way to go, always. I can not wait to use that one.. but alas it is hump day and i need to clean the pad.

    Rubix’s last blog post..Change..

  6. Rubix

    January 2, 2008 at 2:05 pm

    Dear Freddy,

    Please do not use NLP on women. The game is not just about picking up women, it is about improving your own life not hypnotizing women into bed. I admit it is cool stuff but it is pretty lame if you use it in just that way.



    Rubix’s last blog post..Change..

  7. FredEx

    January 2, 2008 at 2:54 pm

    lol Rubix, you scared me man..
    i thought you were talking about me for a sec when you addressed my real name (freddy). but i think the person you meant to address was TEDDY.

    and im not totally sure, but i think Teddy knows not to use alot of NLP on women, he was just saying that if people choose to do that it can come in handy. right Teddy?

  8. lestat

    January 2, 2008 at 2:58 pm

    very good twist to redundant questions women have been exposed to over the years.

  9. Seraf24

    January 2, 2008 at 4:09 pm

    The whole talent question is great for qualification as well as building rapport.

    I’ve been stuck on qualification. Actually, it’s almost non existent in my game. That’ll be a great question to start making my qualification phase better.


  10. Rubix

    January 2, 2008 at 4:23 pm

    OH! haha yeah my bad man sorry about that. Well i hope he doesn’t use NLP and I don’t think he does, at least to that extent anyways. *thumbs down* on NLP.

    Rubix’s last blog post..NLP is lame

  11. teddy bear

    January 2, 2008 at 4:26 pm

    o don’t worry I don’t use nlp for women I don’t like to hypnotize to get laid. that’s why I said ‘if’ you use it. it would be easy to anchor with that question. now I don’t hate or condemn the ppl who use it for game, to each their own. I do use it in my professional life like at the job business wise or in negotiations like buying cars etc

  12. FredEx

    January 2, 2008 at 4:32 pm

    yeah NLP is some powerful stuff if you know how to use it right.. i eventually wanna learn more about it, just so i can have it in my arsenal to use throughout life. also, i think it can be a good tool to talk to women about..

    of course, you wouldnt tell them that it can be used on them, but i think by explaining the basic principles and the psychology of how it works could be a good DHV.

  13. T

    January 2, 2008 at 5:59 pm

    A lot of pickup blogs I found just push product and don’t really talk about anything else. But this blog keeps doing informative and entertaining posts. Keep up the great work in ’08.

    As for NLP, I read about it because it seems interesting, but I’m not really interested in learning it. Don’t really have the patience.

  14. FredEx

    January 2, 2008 at 6:02 pm

    thats the one thing i dont like about NLP.. it really does take alot of patients and time to not only learn how it works, but alot of the time you have to memorize patterns in order to get the result you want. thats why i dont really like using it that much in Pick-up, its very unnatural, and goes everything that a True PUA stands for.

  15. FredEx

    January 2, 2008 at 6:03 pm

    *goes against. sorry lol.

  16. T

    January 2, 2008 at 6:05 pm

    Exactly, in the time it takes to master NLP I feel like I could learn and master a lot more things about social interaction that are immediately applicable.

    T’s last blog post..In Defense of Stereotypes, Part 1: The Two Drives

  17. Rubix

    January 2, 2008 at 8:26 pm

    hey just wanted to report back. I used that “did you have an imaginery friend” one. It was amazing. I used it on this girl that was having a rather shity day and we continued talking and laughing pretty hard about it for awhile.. she didn’t have one but she had 160 rabbits that came out when she was afraid lol… then it ends with this: thank you for making me laugh. seriously. *kisses me*


    Rubix’s last blog post..Txt from Ex

  18. Rubix

    January 2, 2008 at 8:36 pm

    I also have a question, when you use the “are your freinds mostly guys or mostly girls?” question.. if they say guys… if they say girls.. what does that reveal about their personality?

    Rubix’s last blog post..Txt from Ex

  19. Bobby_Rio

    January 2, 2008 at 9:15 pm


    To me that question is more to know what I’m in store for. Personally I hate dating a girl who hangs out with all dudes… it just gets annoying.

  20. Rubix

    January 2, 2008 at 9:50 pm


    Why? I mean I do agree but I never really thought about why before… hmmm.

    Rubix’s last blog post..Txt from Ex

  21. Bobby_Rio

    January 2, 2008 at 10:42 pm


    It really depends on the girl. Some girls are just a little tomboy ish and like hanging with guys. That doesn’t bother me, especially if they are cute..

    But the problem with those girls is that they are usually so cute and cool that all of their guy friends wants to fuck them. It just makes it uncomfortable hanging out with the guys knowing they are waiting in line to fuck my girl.

    Its the clubby girls who hang out with deuchebags that really annoys me. The girl who goes to a club and knows every guy with a blowout there. Now I have to befriend 15 guys i have no desire to talk to. I have to deal with them calling and texting my girl all the time.

    I try to avoid relationships, but if I get myself into one I like it to be with a girl who hangs with mostly female friends (preferbaly hot ones I can talk into a threesome)

  22. FredEx

    January 2, 2008 at 11:42 pm

    VERY nice Bobby.. wow, that is genius.
    i kinda questioned that question too, and i didnt really think much of it as i saw it with no real value to offer, but now that you showed how it can work.. thatll be added to my list for sure, lol. not really as a technique, but more to learn about the girl. great stuff man.

  23. teddy bear

    January 3, 2008 at 12:04 am

    yea i hate girls that have alot of “guy”friends cuz they all have or want to fuck her and they all are pricks and then they try to act all though when youre around cuz they feel threatend

  24. Seraf24

    January 3, 2008 at 1:32 am

    If she has guy friends that are interested in her but she is not interested in them, they are called “orbiters.”

    You never really have to worry about them. Just win them over.

    In fact, have a woman with you if you ever approach sets with men. Almost INSTANTLY disarms them as well as gives you value to the woman/women in the group.

    Have a close female friend I would say. I have a really close friend I’ve known since middle school that became model. She DHVs me everywhere. She’s my wingwoman for life…..


  25. athena

    February 9, 2008 at 3:10 pm

    interesting Q about the girls who are friends with guys or other girls. as a girl who prefers guy friends, i cant tell you that hanging out with other girls involves a lot of drama. too much crap i just dont want to put up with.
    the only girls i DO hang out with feel the same way….i wonder if any strategies have to change with girls like this. for example, i dont think that jealousy ploys will work quite the same way. also, do you have to be more forward? or more careful not to get into friend zone? or do you have to move more quickly? i mean, they DO spend a lot of time with guys they care about who want to boink them. i imagine they spend most of their time defending against this naturally.

    also, i would ask the follow up “how many of your guy friends want to get you into bed?” if she is under the illusion that they “arent that way” or “it isnt like that” or if she gets offended at the idea…well, shes an idiot. im sure some strategies would have to change with THAT knowledge, yeah?

  26. aLpHa_kaY. A.K.A: Kevin

    February 27, 2008 at 2:19 pm

    I like this post so much, i copied and pasted it to a word doc. LOL
    Thats because, my main sticking point is this. Sometimes the conversation goes dry and i automatically ask dry questions. Even after the attraction phase.

    Thanks for this post, and also, this is a link to 15 great convo topics:

    Then expand from that, which could last the conversation forever..Well atleast enough to gain comfort and connection 😛


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