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Good Questions to Ask a Woman on a First Date

Updated on July 29, 2020
Sychophantastic profile image

I'm an eclectic gal with many diverse interests. They include relationships, film, trivia, and an assortment of other things.

Think of dating like a job interview

Guys who are desperate think of a first date as a chance for them to interview for the position of being the boyfriend of the woman they are meeting. A guy with confidence thinks of a first date as a chance for the woman to interview for the chance to be his girlfriend. The first step in approaching the dating game with the right attitude is thinking of it as a job interview for the woman you are meeting. Even if she doesn't know it, the woman is interviewing and you're going to evaluate her and see if she meets your standards. Don't settle for a woman who doesn't pass the test.

Having made the analogy between a first date and a job interview, the intention of these questions is for them to come up in casual conversation, not for the man to whip out a list and start asking them like he's in an interrogation. Be subtle. Gentle. You don't have to ask every question and you don't have to ask them in any particular order or using my exact words. You're trying to create a good conversation, but also get information. Doing so is a skill, so practice.

The ultimate thing to understand though is that if you give the woman the idea that you're the one in control, that she's interviewing for you and not the other way around, it will help overall attraction. You want to give the impression that you're the one doing the choosing.


Use these questions or some variation to start some good conversations

Where Do You See Yourself in 3, 5 or 10 Years?

What you're trying to find out here is whether a woman sees herself married, with children, or an entrepreneur making tons of money. This tells you what she wants out of you because a woman who says "oh, I'll be taking care of my five children at home in my mansion" is a lot different than one who says "I'll own my own business and be making a million dollars."

Describe the Worst Date You've Ever Been on

What a woman considers to be a bad date will tell you a lot about her. It will tell you a lot about what she likes in a man and doesn't like and it will give you great insight into her tastes and what kinds of behaviors you might want to avoid.

Describe the Best Date You've Ever Been On

See #2. However, don't take what she says literally. You're trying to pick out themes, behaviors; etc. You're not trying to repeat the exact details of the date.

Describe Your Dream House

Depending on what kind of guy you are, you want to know what a woman's relationship to money is. Does she even care what kind of house she lives in or does she say something smart like "it doesn't matter what kind of house I'm in as long as I'm with the right person."

Would You Rather Bar Hop or Sit at Home with a Good Book?

This question tells you whether a woman is an introvert or an extrovert and whether she values intelligence more than socializing. If you're a party animal, you don't want to go out with the former. If you're a bookworm, you probably don't want the latter.

What Would Your Ex-Boyfriends Say About You?

This is a fun question for a whole bunch of reasons. First, it's just a good question. You're likely to get a lot of good detail from a woman who you'll want to see again because a woman with confidence and intelligence is going to tell you stuff. She's not going to be ashamed of why she broke up with past boyfriends. And if she's the kind of woman you'll want to hang out with, she's not going to have any big skeletons in her closet. However, a woman who's going to throw up red flags is also going to give you some interesting detail. She's probably going to tell some ridiculous stories. She's probably going to have a whole sequence of stories about ex-boyfriends who were unbelievably freakish. Well, freaks attract freaks. One way or another, you'll learn some interesting stuff. And a woman who won't tell you anything probably has something to hide.

Describe Your Favorite Meal

I find that eating is a critical component of both attraction and compatibility. You want what you believe to be good food to match what your woman thinks is good food. If you like McDonald's and she likes sushi, you might want to rethink your interest.

What Do You Like Best About Your Parents?

You're looking for a bunch of details in this question. First, you want to find out about the relationship between a woman and her parents. Usually a strained or non-existent relationship signals a problem. A preference for one parent or another will tell you lots about your woman. If she's a daddy's girl, she's likely to be looking for similar qualities in her man that she likes in her father. Not a daddy's girl. Similar reasoning applies. Remember, a woman's father is the first and most significant male role model in a girl's life. Pay attention to what she thinks of her father.

Define Success

Is success money or happiness? That's what you are trying to find out from the woman. If the woman talks about material things, then you know what kind of career you're going to have to have to make her happy. If the woman talks about helping others and having a great family, then you know where she stands too. Ultimately, the answer will tell you loads.

Do You Prefer Cats or Dogs?

People have strange relationships with their pets - women especially. You might want to find out if the woman you might be dating is crazy, like if she thinks her pet is a person or deserves to vote or she dresses it in clothing.

© 2012 Sychophantastic


Submit a Comment
  • ThoughtsWriter profile image


    7 years ago from America

    These are great questions. Thanks.

  • savvydating profile image


    8 years ago

    Asking too many interview type questions actually makes women (and men) uncomfortable. I would not accept a second date with a man who seems intent on figuring out whether I am good enough. First dates need to be pleasurable. Period. ...and questions need to be "lighter." There are ways of finding out what people are like by asking something fun, like "If you were a movie, what would you be called and who would play you." That question is straight out of e-harmony.

  • Sychophantastic profile imageAUTHOR


    8 years ago from Texas

    I appreciate the response. First dates should be light and fun. By no means am I suggesting the date be an interrogation, but the smart individual can find a way to ask questions while still being subtle.

  • writinginalaska profile image


    8 years ago from southeast Alaska

    if someone decided to ask me all these questions on a first date, there would not be a second date! sounds too much like a job interview. yuk! I think many people would feel like they were put on the spot and grilled. Not a very comfortable place to be. or maybe it depends on the age and the generation of the dater. I am back in the dating game after a long absence and these are not appropreate questions for every age group. An interesting topic tho.

  • SubRon7 profile image

    James W. Nelson 

    8 years ago from eastern North Dakota

    Again, Sychophantastic, thank you for your heartfelt response.

  • Sychophantastic profile imageAUTHOR


    8 years ago from Texas


    Generally, I respond to comments where a question is being asked. Otherwise, I don't respond. Honestly, it's just a matter of being very busy and not having as much time as I like. Also, my habit of responding just to questions comes from years writing a very popular web site where it just wasn't possible to respond to everyone, so I responded just to questions.

  • SubRon7 profile image

    James W. Nelson 

    8 years ago from eastern North Dakota

    It's a red flag to "me." I don't care to comment on hubs knowing I'm probably not going to get a response. Then there are those who wait till they've gotten about 20 comments, then respond to everybody at once with usually just "thank yous," which, of course, is better than nothing. To me, a good hubber sends a personal response to every comment.

    But, hey, this is just me.... Thank you for the heartfelt response.

  • Sychophantastic profile imageAUTHOR


    8 years ago from Texas


    Why is only responding to one post a red flag? Also, this isn't a caricature, it's a self-portrait. I'm just not a good artist.

  • SubRon7 profile image

    James W. Nelson 

    8 years ago from eastern North Dakota

    Sychophantastic, first, I would take you more seriously if your profile picture was of you instead of a caricature. However, I enjoyed this hub and read another one of yours about dating and enjoyed that one too. I see you've responded to only one of the people who commented. Another red flag as far as I'm concerned. Good job on the hub, though.

  • dashingscorpio profile image


    8 years ago from Chicago

    Your admirer, In a way I agree with you. Every question someone asks or (does not ask) tells you something about them. And I agree whoever is asking questions is (playing the music) and the person answering is doing the (dancing). However dating should never be about "who is in power". The first step is to have fun and determine if there is any chemistry to justify going out a second time. The next steps are to find out over time if you share the same values or want the same things at (this moment in life). The reason why so many people hate dating is because they are too afraid to "relax" and be themselves. Until someone reveals their "authentic self" you won't know what you're dealing with.

    Keeping things light or casual early on causes people to open up a lot quicker than having them try to guess what it is you want to hear. A first date is all about having fun! (enjoy the concert, the lunch/dinner, the play, county fair, movie, or whatever).

    If the two of you don't have a great time on the first date then odds are there will not be a second date.

  • Your admirer profile image

    Kkavya Sharma 

    8 years ago from Delhi


    At one point I have to agree with you. We don't need to buy our wife, its just a first date. But the questions he put up there are some good questions and gives the women some clues about the personality of the man. The fact that he is qualifying her will subconsciously tells her who is in power. But you need more than just posting questions in front of her.

  • Your admirer profile image

    Kkavya Sharma 

    8 years ago from Delhi

    Some questions are good but I am not in favour that you should ask all these questions. I would rather pick one of above question as an icebreaker and then communicate further based on the response.

  • Kimberly Vaughn profile image

    Kimberly Vaughn 

    8 years ago from Midwest

    I never thought about a first date like this but these are great suggestions!

  • ambercita04 profile image


    8 years ago from Winter Park

    Great job! These are questions I have asked numerous times when I have gone on dates and they are key to helping determine whether the two of you would be a good match and if dating furthur is worth it. Enjoyed your article!

  • Sychophantastic profile imageAUTHOR


    8 years ago from Texas


    You are so right! A first date should be light and fun. Although I pose this article as a way to get information, I wasn't suggesting you have a laundry list of questions that you rattle off to a woman like dictation. That obviously wouldn't work. I was hoping my readers would be more subtle (and as such, I'm adding a note in the opening paragraph). That being said, having the confidence to project to a woman that you are interviewing her and not the other way around will help create attraction, not hurt it.

  • dashingscorpio profile image


    8 years ago from Chicago

    Being a man myself I have to say I have never asked any of these questions on a (first date)! In fact it's more likely that a woman would ask a man these questions.

    The number one reason a man asks a woman out is because he is physically attracted to her. His next goal is to determine if her personality and sense of humor are in line with his. A man has no interest in hearing about what you did with other men! That is not something he wants to think about or visualize during a first date!

    Men are not interested in knowing what a woman's "dream house" would look like or what qualities she values in a parent. We're not trying to figure out where a woman sees herself in 3, 5, or 10 years from now. It's just a "date"! We're not shopping for a wife! We want to get a feel for how things are going today. We want to know what a woman enjoys doing in her spare time. Our main objective on a first date is to see if we have chemistry with one another and have some fun! Truth be told we don't want to be (asked) the questions in this hub. It's too much too soon. Keep things light and have fun on a first date.

    It's not like we're trying to figure out whether we should cut the red wire or the blue wire. LOL! One man's opinion! :-)

  • Alecia Murphy profile image

    Alecia Murphy 

    8 years ago from Wilmington, North Carolina

    You did a great job with these questions! I like how you transposed what employers ask to the dating world. Great hub!

  • Jeannieinabottle profile image

    Jeannie Marie 

    8 years ago from Baltimore, MD

    You are so right on this.... I think of dates like job interviews, too. After the "first interview" you sit by the phone hoping for a "second interview" in either situation, too. Great advice and voted up!


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