“Who they attractin’ with that line, ‘What’s your name, what’s your sign?’”

-Notorious B.I.G., “Big Poppa”

That song came out in 1994, yet more than two decades later, we’re still asking girls the same boring questions.

Asking questions is a great way to get to know that girl you like a bit better, but that depends on the kind of questions you’re asking. Girls get asked “Where are you from?”, “What do you do?”, or “What are your favorite hobbies?” all the time, so their responses are pure reflex.

You see a hot woman drinking coffee alone, what do you ask her?

Asking boring or simple questions will get you boring or simple answers, and that’s no way to build a connection — you need to ask questions that make her think. If you do, two things will happen:

  1. You’ll show her that you’re not like other guys — you have depth.
  2. The more complex her answer, the more things you’ll be able to use to build the conversation.

Here’s how to come up with the kinds of questions that will get her fully engaged in the conversation.

Use The Past/Present/Future Method

A good conversation is a give-and-take. You can’t just bombard her with questions, or she’ll feel like it’s an interrogation. Instead, give her information about you while you ask about her, and the Past/Present/Future method is a perfect way to do it.

“She is not going to divulge much, unless you give her a little about you”

In a nutshell, the “Past/Present/Future” method combines a statement about your past, present or future with a related question about her. I’ve split them up into three sections, and because I’m such a nice guy, you’ll also find sample questions for each category. You’ll need to tweak them to make them your own, though — I can’t do everything for you.

Past References

You reference something in your past — could be last week, could be a year ago, could be from your 5th birthday — then ask her something about hers. The goal of the “Past” questions is to give her a better idea of what made you the person you are today while learning the same about her. Everyone loves a good origin story. Why do you think there are so many Spider-Man reboots?

Discussing the past provides more information about your roots

Here are some examples.

1. When I was young, I wanted to be [mention a silly childhood dream you had]. Did you have any ridiculous goals or dreams when you were a kid?

2. Last month, I [mention a place you visited recently], and I’ve been dying to show it to someone else. What’s one place you love to introduce to new people?

3. Last year, I tried [mention a unique kind of cuisine] for the first time, and ever since then I’ve been trying to expand my palate. What’s the weirdest thing you’ve ever eaten?

4. When I was a kid, we had a family tradition that [mention a family tradition]. Did your family have any traditions when you were growing up?

5. I remember working at [mention your worst job and why it was terrible] — I can’t even set foot in that place anymore, even as a customer. What was the worst job you’ve ever had?

Present Questions

The Present questions, give her an idea of who you are now. It’s a good opportunity to highlight your interests while asking about hers, which helps you decide if you two are compatible. It’s also where you can try to slip in a little bragging, too — just be sure not to overdo it.

You might find you have the same interests such as traveling.

Here’s how it works.

6. I spent the afternoon [mention an activity you do regularly] — I really enjoy [mention the part of the activity you like most]. What’s the one activity you can’t go a day without doing?

7. I just watched [mention a movie] for the first time — I know everybody says it’s amazing, but I didn’t enjoy it that much. Are there any movies that you don’t like but that everybody else seems to love?

8. One of my favorite things about my neighborhood is [mention something you really like about your neighborhood]. What do you like most about where you live?

9. I’m trying to learn how to [mention a skill you’re trying to learn, like playing the guitar], but it’s been tough so far — I guess I’m just not a natural. What’s one skill you wish you had?

10. I’ve set a goal for myself that I’m going to [mention a goal you have]. Do you have any goals you’re working towards right now?

Future Questions

The Future questions are where you can really set yourself up for success. When you talk about the future and ask the girl you like about hers, you’re effectively sharing your long-term goals and dreams with each other. This can be a great way to get her thinking not just about her future, but what her future might look like if it included you.

Plant a seed to make her think about a potential future together

For example:

11. I really want to take a vacation to [name a location]. If you could pack up and go anywhere in the world, where would you go?

12. I’m going to buy a lottery ticket tomorrow — I know it’s a long shot, but if I win, I’d [name something you’d do if you won the lottery]. What’s the first thing you’d spend the money on if you won the lottery?

13. By the time I’m 40, I’d like to [name one of your life goals]. What do you envision your life being like by then?

14. I’d really like to live in [name a foreign country]. Maybe not forever, but at least for a little while. What’s one country you’d like to live in for a while?

15. I have a bucket list, and one of the things on it is [name something you want to do before you die]. What’s one thing you feel like you have to do at least once in your life?

A Few Tips

Of course, it’s not as simple as just asking these questions and waiting for the sparks to fly — there’s more to it than that. Keep these tips in mind to make the most out of the questions.

Show Interest & Listen

Asking the question is only the first part; the rest is building a conversation based on her answer. When you ask a question, practice empathic listening — don’t just listen to what she’s saying, but how she says it. [R]

It’s Not An Interrogation

You shouldn’t ask questions just to ask them — you should be asking because you’re genuinely interested in what she has to say. If your conversation is a car, then the right questions are the gasoline: they keep things moving, but if you use too much, the whole thing will stall.

Be Enthusiastic

Enthusiasm portrays confidence during conversations

Finally, enthusiasm is crucial — you should be excited to hear her answers, because those answers tell you more about her. If she feels like you’re excited to learn about her, she’ll be more willing to open up to you.

If you find yourself fumbling for the right questions, give this list a try. The next conversation with the girl you’ve had your eye on will be a breeze.

However, if you feel you want to ask her right out without going through all the motions, then your success rate in very much dependant on the use of certain words and taking advantage of human language processing as shown by Say Hello Women, one of the best programs on approaching women

Resources & References

Concerned you may run out of things to say after using up your list of questions? Check out our sources for tips on how to keep the flow going naturally.

  1. Asking questions is only the beginning of what could be a meaningful relationship. If you want to take it to the next level, then guys over at Win With Women have this awesome article on ways to get a girlfriend you might want to check out.
  2. 7 amazing questions to ask on a date (or when you first approach her) by Tripp Advice
  3. Once again by Tripp Advice who shares how to keep a conversation going (a simple trick to keep the conversation going if you run out of questions)
  4. 5 tips for empathetic listening – LifeHack by Reginald Adkins