10 Questions to Ask a Woman or Girl on a First Date

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Think of dating like a job interview

courtesy photostock freedigitalphotos.net
courtesy photostock

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.

  1. 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.”
  2. 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.
  3. 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.
  4. 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.”
  5. Which would you rather do: sit at home with a glass of wine and a good book or bar hop with friends? – 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.
  6. If I called your ex-boyfriends, what do you think they’d 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.
  7. Describe what you consider to be good food. – 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.
  8. What are your favorite qualities in 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.
  9. 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.
  10. 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.

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