First date questions are usually very generic, standard, dull, and dry.
Is this a bad thing?
Then, there are those dates which might require a bit more than generic first date questions.
You may be out with a lady that is a bit more intellectual and demands a bit more of a cerebral challenge.
She is just not one of those ladies that finds the same dull questions worth listening to.
It’s one thing to come up with great first date ideas and a completely different thing to spring up fantastic first date questions to buckle everything up.
That is why the following first date questions are arranged on a topic by topic basis so it’ll be a lot easier for you to follow.
So let’s go ahead and get started with the first one.
What Will I Learn?
- Investment or Finance
- But, isn’t that a dull topic?
- What is the absolutely riskiest investing strategy or venture you would love to get involved with and know you should?
- What do you think of all those infomercials out there promising cool investment strategies and paths to riches?
- What would be the best thing for me to do with my money?
- Extra First Date Questions
- Are you going for something organic or something processed?
- Any suggestions I should add to my Netflix account?
- Can you suggest some apps for my iPhone?
- What would you do with a billion dollars?
- What is the absolute scariest thing you have ever done?
- If you were an alien from space and couldn’t look like a human, what would you want to look like?
- Do you like to give out Thanksgiving cards?
- What are some of your favorite side dishes to eat with your main serving?
- What is it you don’t like about your job?
- Have you ever cheated on [fill in the blank]?
- Have you ever used drugs, prescription or otherwise?
- What were your favorite cartoons as a child?
- What are the most memorable toys you had as a child?
- What did you do on Saturday nights when you were a teen?
- Is there anything on the menu you know you shouldn’t have?
- Does your physical or mental energy kick in first when you wake up in the morning?
- Do you ever look for a life-changing moment?
- In conclusion…
Granted, if you DO go to a museum to check out things like these, you probably will have a lot of fun doing so.
In fact, museums are so much fun that they can make excellent first date adventures.
And seriously, if you are stuck for first date questions, how could you not come up with a ton of them when using a museum for your subject matter?
There is a whole world of history (literally) inside a museum.
But, you may wish to ask these questions when you head to the coffee shop afterward.
Actually, since I am not sure which museum you will be visiting, I have added one question per “genre” of the museum:
Did you like the experimental, impressionist, or surreal paintings on the exhibit?
Of course, you can substitute any other mode of painting that may have been on display.
Just make sure that you have the genre right or you may look a little silly.
What did she like about them? What items on display could she have done without?
All visitors to a museum who consider them fans of the art world will likely have strong opinions of artwork.
Why not give your date a forum for her opinion?
She will likely appreciate it.
What would be the one famous museum in the world you would love to see?
What a shame no one had ever asked her opinion of where she would like to go.
Now, you have corrected that unfortunate oversight and, hopefully, you will make a good and sincere impression on her.
Do you think museums of this nature preserve history well?
This is a sneaky question because it can fit ANY genre.
More than likely your date will say yes because, well, all museums preserve history because that is the whole idea of a museum.
Anyway… first date questions like this serve a very basic and simple purpose.
They are intended to use the museum as a foil for coffee shop conversation.
Really, if you have just left a museum, would you not want to ask questions based on what you saw in the museum?
Simple first date questions such as this are, well, quite simple – so why not use them?
You do not have to come up with anything profound.
Keep your questions simple like this and they will work well for you.
Why not use these venues to your full advantage?
Has not the increased interest in the art and science of meditation taken you by surprise?
While you may have been practicing it for some time, a great many practitioners are completely new to the venture.
What led them to become interested in it?
More than likely, if you like meditation, then you have probably ventured to yoga classes or Buddhist self-help lectures.
In doing so, you may have gotten a phone number here and there, and that has taken you to the precipice of a first date with someone that shares your interest.
Okay, you might be saying that you know how to “do” meditation, but you are not all that versed in talking about it.
All you really need to do is ask a few questions on the subject and allow her to do the talking.
So, here are three questions to meditate on the next time you venture out on a date with a fellow New Ager…
What are the greatest benefits that you have gotten from meditating?
This can be an intriguing question to ask because it is so much you can learn from the answer.
What are the benefits that she has gained?
Let’s say she discovered meditation helped her improve her self-esteem.
If you never thought meditation had the potential to do this, now you know it does…
And this could be an inspiration for you.
The act of meditation is often an indication of the motivations of the person meditating.
Once you understand some of the motivations of the person, you will begin to understand the person as well.
Do you have any tips on how to make meditation more beneficial and impactful?
A question like this is appreciated because they do show your interest in the person as well as an interest in a person’s opinion on things.
It is most definitely never a “minor thing” to ask a person for their opinion, advice, and help – and that really is the crux of this question.
It gives her a chance to shine!
Give her that opportunity, and you likely will make a very good impression.
Do you have a favorite music selection or audio recording to listen to when you meditate?
While it is commonly recommended to meditate in silence, very few people actually do.
Sure, you are supposed to empty the mind and all that jazz, but the truth of the matter is most find sitting in silence eerie.
If she is listening to self-help recordings, this would be far more revealing than if she listened to the generic New Age muzak.
It is a definitive fact of life that girls love sports.
And this refers to all manner of sports, including team and solo ventures.
Even X-Games may fit into the equation.
If you do have a date with a lady that loves sports, then you can rest assured that the two of you will have a lot to talk about.
You can sit back and listen to your date’s responses and opinions.
First dates with someone really need to require you to sit back and listen.
This will allow the date to go a lot smoother than you ever thought it would.
Why is that?
It is a topic that has the ability to talk for itself.
Sports is such a diverse subject that it can go in many different directions.
This is why it sets the stage for a number of great and simple first date questions.
What is your favorite sport?
Remember, this is a topic that is best kept simple, at least from the beginning.
You likely do not want to get too involved with asking questions that deal with a lot of sports trivia.
How do you know she is that knowledgeable about the subject?
Simple and basic questions such as this set the stage for learning more…
And that is a good thing.
Again, simple and basic starters such as this get the proverbial ball rolling.
What athlete or sports star inspires you the most?
What is it about a particular athlete that your date finds appealing or intriguing?
If you want to know, all you need to do is ask her. You might even be somewhat surprised at the responses you hear.
Once again, you will never know what her response will be until you ask it. And you should definitely ask it.
Do you collect sports memorabilia?
It is a common assumption that it is a real guy thing to collect sports memorabilia.
To a degree this is true, but it would be unfair to completely dismiss women from the equation.
If your date is a big fan of sports, then it is likely she owns SOMETHING.
If you want to know what it is, then all you need to do is ask.
That is the essence of all first date questions on any topic.
How could it not be?
It is such a wide and diverse topic that you will always have much to probe and discuss.
And if she really is a true sports fan, she will certainly enjoy all the discussions.
You might have a closet door that won’t close or a leaky faucet that just drips on into infinity.
- How can you fix these things?
- And what are you going to say on your first date with a lady you have long since been interested in?
Okay, at this point you may be wondering what one has to do with the other.
Well, if your date is someone that likes do-it-yourself (DIY) adventures, you will have a lot to ask on the date.
There are two huge benefits to asking DIY oriented first date questions.
- The first would be you can give your date a great chance to shine by offering insights into her experience.
- The second would be you might actually learn how to improve your cabinets!
Don’t believe so?
Here are three excellent ones to examine:
When did you first become interested in DIY endeavors?
You do not have to ever venture beyond the basics, because anything more than that runs the risk of confusing your date.
Do you really want to put her on the spot with tough-to-answer first date questions?
Asking her how she first became involved with DIY projects likely has a story behind it.
You won’t know the story until you ask.
What is the best way to start in DIY projects?
Again, she has a lot of experience in the process.
That means she probably has a lot to talk about on the matter and she will likely offer you a lot of advice regarding how you should start your own DIY adventures.
Such a question is a great one because it can display sincere interest, which certainly will help boost attraction levels.
Are there any great books or television programs that are perfect for beginners at DIY projects?
What would be the prime word in the above question?
You guessed it: beginner.
The employment of this question is a somewhat sly one.
It serves the purpose of establishing your date (which she is) and you are the student (which you are).
You avoid coming off like a big know-it-all having all the answers on the date.
Truth is, you don’t want to have all the answers.
You just want to have quality first date questions.
Investment or Finance
These days, people are looking for a new, novel, and original vehicles in which to make their money work for them.
There just is not the same faith present today with traditional investment vehicles as there was in the past.
But, isn’t that a dull topic?
If your date is one of these people, you have quite a few lively first date questions you can ask.
Your mission here is that you want to avoid asking dry and dull questions which do not move things forward.
Instead, you need a few lively questions that will make the date even livelier.
What is the absolutely riskiest investing strategy or venture you would love to get involved with and know you should?
She might answer “dating” if she has a humorous side.
Odds are strong if she is a serious investor then she likely will have strong opinions on anything high risk.
She might even be someone that THRIVES on high-risk ventures and investing.
You might learn a lot about both finance and her.
What do you think of all those infomercials out there promising cool investment strategies and paths to riches?
SHE HATES THEM.
Trust me, she hates them and now she is going to vent!
Don’t worry about it, since she is not venting about you.
And she did intend to miss them, but she came across them when flipping channels on television… right?
Now, she is going to share her opinions on the subject, and you are the person who will be hearing those opinions!
Whoever said those awful late-night infomercials are completely worthless?
The answer is mostly everyone.
What would be the best thing for me to do with my money?
This is a question that your date will find interesting because it puts her in the expert’s seat.
Why will your date find this question interesting?
What is the point of that? They assume it helps them make a good impression.
Set yourself apart from the crowd by asking for her opinion and advice.
Doing so will make a good impression.
Whoever said money and finance was a boring topic for first date questions?
A million or so people have.
In a lot of instances, they are correct.
Extra First Date Questions
Are you going for something organic or something processed?
Is this an odd question?
Coffee shops these days will have cookies, cakes, and beverages that are loaded with processed and refined sugars.
Then, there are those more “Whole Foods” oriented items which are natural and organic.
This may seem like a throwaway question, but no question is without value if it helps progress your date.
Any suggestions I should add to my Netflix account?
This is really a spin on the classic question “Have you seen any good movies lately?”
The problem with the classic version of the question is that it is dull and boring and comes off as scripted.
Asking questions in a manner such as that really does not help set you apart from all the other guys out there.
Can you suggest some apps for my iPhone?
Our society has become more and more technologically oriented over the past two years.
The leaps that have been made in technology have been quantum leaps.
There are certainly a large number of these apps, and they serve a lot of different purposes.
Some are for fun and games, and others can help you with your professional pursuits.
Which ones should you download?
Ask your date!
She likely has a lot of recommendations.
She might even show you all the apps she has on her mobile device.
While not intellectual or thought-provoking first date questions, they aren’t exactly likely to hurt your cause.
What would you do with a billion dollars?
There is a whole lot you could do when you are given a billion dollars.
Of course, she is going to say that.
She certainly does not want you to think she was selfish.
Truthfully, you would likely do the same thing if you were asked the same question.
As such, you are going to need to probe for the things she really wants!
There are no right or wrong answers she can put forth.
Whatever her response might be, just listen to it and soak it in.
It’s the first date.
Have fun on it.
What is the absolute scariest thing you have ever done?
The response she gives might scare you away!
Nah, she is not going to admit to anything too outrageous in terms of her behavior.
The way to do that would be to come off as a unique and fun loving guy.
One way to do this would be to ask fun and off the wall question such as this one.
Then, all you have to do is sit back and listen to her response.
Or, it could just be what it is… a scary tale!
If you were an alien from space and couldn’t look like a human, what would you want to look like?
I am not going to lie to you. This is not exactly a question you’ll want to ask the minute you sit down across from your date.
But, you already knew that, did you not?
You did know that, right? (I hope so!)
The answer to this question is about as irrelevant and irrelevant can be.
It will be a lot of fun to hear her response, which is why you asked it in the first place.
While the opportunity for asking questions such as this are limited, they do arise.
Why not give it a shot when the door opens?
What do you think about turkey alternatives such as ham, goose, or duck?
(Whoops) You never know though.
She may have had one of those atypical Thanksgiving dinners at some point in her life and she may have good (or less than stellar) memories about it.
She might even be thinking of substituting one of these selections for next year’s Thanksgiving.
She might even recommend a website with a lot of recipes for these dishes.
Do you like to give out Thanksgiving cards?
Thanksgiving is not always thought of first, second, or third when it comes to the volume of greeting cards sold per annum.
However, some folks are into giving greeting cards, and your date just might be one of them.
Those that try to be impressive and profound generally falter on both counts, and that can have dire consequences.
Mainly, the date will falter.
What are some of your favorite side dishes to eat with your main serving?
You could consider this question to be a sequel of sorts to the first question.
But, what do you eat it with?
Don’t deliberate on the question.
Ask your date.
Some might be standard side dish options and then there might also be a few unique and original selections she suggests.
This is definitely not a question where you will get a blank stare or a one-word answer.
She will probably have a strong opinion on what side dishes are perfect for Thanksgiving.
Thanksgiving or any holiday for that matter can provide a lot of material for first date questions.
Hey, the material is there, so why not take advantage of it?
What is it you don’t like about your job?
Eek. Just eek.
This is a really bad – as in way out there bad – question.
In other words, how do you know your date dislikes her job? She might be THRILLED with her job.
To ask her what she doesn’t like about it might lead to a really annoyed and quizzical look.
That does not build attraction, and you are headed downhill fast.
Does this sound like a really good first date conversation material? It doesn’t because it flat out isn’t.
Don’t ask a negative question like this. It only has downsides.
Have you ever cheated on [fill in the blank]?
Guys, what type of person do you ask if they have ever cheated on someone/something?
You would ask… a cheat!
This seemingly innocuous question is really a serious insult to the individual you are asking such a question to.
Actually, I have a much better idea.
Don’t ask this question.
Just flat out don’t ask it.
Have you ever used drugs, prescription or otherwise?
No, I am not making this one up.
This one is bad.
It is really bad.
Yet, this question does pop up on dating blogs and advice websites.
Again, you want the person you are out on a date to have a fun and enjoyable time.
Questions such as these are downright nutty, because no matter what answer you get, what does it do for you?
Not a whole lot! Avoid questions like this… avoid them!
Bad first date questions are really poor choices because they serve no purpose.
Guys, they aren’t.
There are much better questions out there you can use, so why not use them?
What were your favorite cartoons as a child?
Depending upon the age of your date, she will either mention Saturday morning cartoons or after school cartoons.
Okay, all that is well and good.
The pop culture history lesson is over and now we need to move onto the subject of first date questions.
Why is this a good first date question?
It simply cannot have a bad response.
After all, you didn’t ask her about her least favorite cartoon.
What are the most memorable toys you had as a child?
What would childhood be without a favorite toy?
More than likely, your date had quite a number of toys which she remembers.
You could tell her that “Barbie doesn’t count”, so you might need to press for her second favorite toy.
Either way, you need to help take the conversation into a lighthearted trip down the memory lane of childhood.
While not the most popular of first date questions, it can be a good one.
What did you do on Saturday nights when you were a teen?
You know what?
She might not even give an honest answer to this question.
You are asking the question just to make light, fun conversation.
Again, questions such as these are not exactly ones that are commonly asked so they will set you apart from the crowd.
There is always something on the menu that both guys and girls want and both know they should avoid it.
How can you stay in shape if you order something that is 1500 calories?
Well, you can always work out the next day, but that is not what’s important right now.
Asking very basic and simple questions such as this are an easy way to get through the date without really causing any controversy.
This question has a tinge of humor to it as well, which also adds to its value.
Does your physical or mental energy kick in first when you wake up in the morning?
This is not an off the wall question, because it’s a really basic straightforward one.
Maybe both end up working together at the same time first thing in the morning when she wakes up.
Regardless of which one happens first, something will happen.
Ask her which is which.
She will likely have a quick answer to this query.
All you’re doing is just making an honest inquiry to see what the response is.
Do you ever look for a life-changing moment?
This is a bit of an “over the top” question, so it needs to be asked at an appropriate time during the date.
However, it’s one of those questions that may lead your date to ponder it a bit.
If this occurs, you are saved the potential horror of having to say something that leads you to stick your foot in your mouth.
Who was/is your favorite antihero?
This would be the basic quintessential first question to ask.
- How can you even broach the topic of the classic character of the antihero without asking which one of the great dark heroes of pop culture is her favorite?
- Is she a fan of classic antiheroes such as The Man with No Name or the cold assassin Jason Statham played in the remake of THE MECHANIC?
- Does she like classic literature characters such as Winston from 1984 or does she lean towards more fantastic antiheroes along the lines of Batman?
Do you like antiheroes from film, television, literature, or real life?
There are antiheroes everywhere, and they can either be intriguing, scary, annoying or a mix of all three and then some.
Are there any your date is fond of?
More than likely, if she is a fan of pop culture and the image of the antihero, there is a specific medium in which she likes to investigate her antiheroes.
What type of antihero would you be if you could be?
(Then again, what’s to say she is not an antihero now?)
This can be considered a question that adds a sense of whimsy to the equation.
Basically, this question shifts the burden of your date from having to be revealing about herself to… revealing herself by proxy.
Yes, we did say at the outset this direction of first date questions would be of the cerebral variety.
First date questions aren’t supposed to be boring and sloppy.
They say; ‘First impression matter most’.
And I couldn’t agree more.
Truth is, first date questions can either make or break your chances of getting a relationship off to a great start.
That’s the crux!
That’s what I want from you.
Many people can’t do that.
So, go make it happen!
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