8 CREATIVE QUESTIONS TO ASK YOUR DATE

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I’m analytical. It’s how I learn things. It’s how I learned to speak Spanish and to dance salsa. I break things down into little bits and analyze them for absorption into my brain.

My dating life has been no different. Sexually, I grew up late. The very first trace beginnings of my sexuality started sometime in the middle of high school. When I say trace, I really mean it. Nothing really happened between me and a girl until the end of senior year when I had my first girlfriend. It got mildly better in college, but things only happened by chance, which wasn’t often.

Dating to me is like a computer program. There is a correct way to do things. There are many paths to the desired outcome. But, underneath the ‘front-end’ is the ‘code’ or the process of dating.

On my super-secret excel document, I have laid out my life. One tab per section of my life. I could write a series of books on my approach to dating. How to meet someone, how to build attraction, how to vet them, how to make them feel comfortable, how to strengthen the connection, unique date ideas, answers to the question ‘You are perfect. Why don’t you have a girlfriend?’. Joking.

Let’s get to it.

Typically, in a “pick-up” scenario, the man leads based on the woman’s physical attraction. Initially, she has the upper hand and he has to attract her. It’s not uncommon for the man to have to do 90% of the talking, at first. At some point, ideally, the woman will realize that she is attracted to the man. Now it’s his turn to find out if [insert question two].

These questions are ONLY to be asked after you believe she realizes that she enjoys your company and, ideally, is attracted to you.

If you ask one of these questions too early, it’s going to be awkward and will probably end the interaction. That’s because they’re not easy questions.

As the man, you have to picture yourself as the person selling something on the street. How do you feel when this person approaches you on the street? You are wondering what do they want and are forming escape routes. The last thing you are going to do is answer a complicated question which means you have to give them more of your time. No, you say the least amount as humanly possible without being a total dick. It’s because you’re not invested in the conversation yet.

Back to the questions.

You’ll see right away that these are not standard questions. That’s the point. A woman has talked and answered questions 1,000 times more than any man. Think of the last conference you went to and how many times someone asked you what you do. How quickly did that get old? Well, that’s a woman’s “everydate” life with questions like ‘where are you from?’, ‘what’s your name?’, ‘what’s your job?’.

Instead, try to excite different areas of her brain. Plus, I believe these questions let you get to know each other quicker, let’s her know that you’re different, and opens up more conversational loops and opportunities.

Pro tip: next time you’re at a conference, try asking ‘What goals brought you to this conference?’ instead of ‘what do you do?’

Bonus: In the beginning, see how long you can go without asking her the basics like name, occupation, age, etc.

1. Are you the type of girl to get into a pool quick or slow?

If this sounds like an odd question to ask, well, that’s because precisely it is! Guaranteed she’s never heard this before. 100% of the time I ask this question I get a positive response that usually starts with a smile and ‘oh, that’s a good question!’

If she says quickly, you can assume she’s more the spontaneous type. She may be a partier. Or, does she not answer the question and instead ask you questions (is it a pool or the ocean? Is the water warm?)? Does she say it depends?

These all give you clues into how her brain works. Ask the question and see where the conversation goes.

2. Is there more to you than meets the eye?

This one is just plain fun. It also takes balls to ask this to someone’s face. Don’t believe me? Try it. It’s a bit of a backhanded compliment.

I ask this and pause. It’s interesting to see how she takes it. You’ll know almost immediately after this question where you stand. If she is offended, then you either asked it too early (less likely) or she is not interested in you (much more likely) and is using it as an excuse to exit the conversation.

If she starts telling you about who she is behind her pretty face, stay calm, but she is likely interested in you.

3. How do you keep yourself entertained if no one is around?

I like to ask this to find out if this person is the type to watch Netflix all day long or if they actually have hobbies. Unfortunately, an alarming amount of the time I ask this question, I get answers like sleeping, watching Netflix, eating. ugh

4. When was the last time you were really excited?

Like really excited. Like couldn’t sleep excited. Just ask to find out. This will likely lead to a conversation. It’ll likely be hard for her to think of this, though. I mean, when was the last time you were so excited that you couldn’t sleep?

This brings up a good point. Anything you ask, you need to have an answer to.

5. What are you an expert at?

Similar to #3, but I really try to peel back the layers and find out who this person is behind the Netflix binge-watching, desk job, and sleeping in on the weekends. Everyone has a special talent.

I’m an expert at weight-lifting, Airbnb, poker, and soon-to-be-expert in handstanding. Besides weight-lifting which has physical effects, you’d never guess at the other two if you didn’t already know me. Dig to find these hidden talents.

I met someone in Canggu, Bali that was an excellent (and I mean world-class professional excellent) handstander. You never would know this seeing her walk on the street or really doing anything besides handstanding.

6. What are some things that would make me want to get to know you better?

You are awesome. How come girls don’t approach you in everyday life? I mean, I don’t know you, but I’m pretty sure you are a well-rounded gentleman that many women would be lucky to be with.

You are nice, funny sometimes, overall normal. You are healthy, you have a good relationship with your family, a good job, you go to the gym on a weekly basis. You have a strong social circle and a great smile. Isn’t this what all women want?

Well, these are things that would make a woman want to get to know you better. So, ask her this.

7. If you could not fail, what would you do right now?

One of the more typical questions stated differently. It will reveal her passions. You can follow up with asking what are the obstacles preventing her from doing this now.

8. What is both one thing that you do not have and do not want?

Oh, boy. I saved the best for last. This one is tough! Think for a moment for yourself.. What did you come up with? Paste it in the comments below. I want to know.

This is such a hard and thoughtful question. It’s actually part of a longer thoughtfulness exercise I read in an NLP book. We know what we want, but don’t have (more money, a bigger d*ck, larger shoulders). We know what we don’t want but have (a crappy job). We know what we want and have (loyal friends, health, a Netflix subscription). But we don’t generally think about what we both don’t want and don’t have.

Remember, to ask this, you must have a ready answer. Tell me your answer in the comments.

Bonus: This or That Game

I made this game up rather recently. It’s super simple and involves you asking a few questions about things that are important to you to either have in or not have in a potential partner. You are going to give a series of options, two at a time. Your date has to choose one and lose the other. I recommend you make your date promise you to answer all the questions if they decide to play. They’re tougher than they seem!

Here are my current four “this or that” questions:

1. God or Health (based on what you already know about the person you can change the first to Health or Family or God or Family)
2. Health or Family (if they answered the same answer twice – Health for #1 and #2 in this example- then you’ll actually have 5 questions, in this case it would be ‘God or Family’)
3. Fast Food or Sweets
4. Drugs or Alcohol

These questions tell me a lot about a girl! How much she values three very important (health and family) or not important (god) things plus some bonus info. Obviously you can ask anything: Amazing Experiences or Ton of Money…or…Home Alone or With Friends.

Additional Bonus: “How’d you get into what you do?” (Thanks to NLP: The Essential Guide) is a better, more unique way of asking what they do for work that will often lead to additional insights.

Conclusion

These questions are meant to be unique and open the doors to getting to know each other better.

Even though questions like ‘Is there more to you than meets the eye?’ and ‘Why would I want to get to know you better?’ seem condescending, they actually will reveal a lot about the person you are talking to. And, it will reveal exactly how interested she/he is in you. Getting defensive early on while getting to know someone, when you’re supposed to be on your best behavior, simply means they’re not interested.

Say them with the mindset that you are really trying to deeply get to know them. Say them with a smile. But say them seriously.

Now that you’ve read the questions and my thoughts on them, which is your favorite?