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I have never been a person who likes small talk much, I would much rather have a deeper, thought provoking conversation with someone and get to know them on a deeper level. I am looking for a few great question to help make this happen more. What would you ask a close friend/ family member or lover/partner if you could ask them anything to have an insight into who they really are, feel and think?
Thanks all for your replies, but I think I should explain more of why I asked and what I am going to use the questions for.
I am looking to make my own, Big Talk type game to play with friends, family, lovers, etc. I am breaking the questions up in categories/topics. It can be played with only two people to many people and because the players get to chose what topic they draw a card from they may feel more comfortable. I never have had a hard time asking the hard questions or having deeper conversations with people, even strangers but I wanted to get questions from a larger pool of people, not just what I come up with. Thought the people of the many groups here might have a greater insight.

Mermaidfantasy 7 Sep 2

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Not without being extremely intrusive. I find it a turnoff when people try to directly make me say things I'm not ready too.

Mabey you should initiate a deep conversation by talking about deep things yourself, or by answering their questions in a deep manner. It's not the questions but the conversation around it.

MsAl Level 8 Sep 2, 2019

Can you believe this weather? 😉


@LeighShelton I'm glad someone can because I can't. I mean just yesterday I walked out the door f the house in the morning (early, you know? Taking my son to school. Well, not to school per se, but to the bus stop, which is actually at his school, or one of his schools. He attends two different schools, one in the morning, and one in the afternoon. The morning one is almost an hour further than the afternoon one. If only it was the other way around, we wouldn't have to get to the bus stop, the afternoon school, so early in the morning).

@CallMeDave thats really inconveniant but living in england you can litterally get all weathers in one day mot times of the year so i still say yes.


If you could kill one person just by concentrating and willing it, is there anyone that you would use that ability on? What would be your ideal taco? What would be necessary for you to be willing to take a one way trip to Mars? If the existence of a god were provable, would you want to know? What would you do for 3 Klondike bars?

great questions, could be fun and funny or deep.

Trump or that prick allowing the destruction of the amazon


'"What was the best thing that happened to you today?" That could lead to "Why was that the best?"


Fear of vulnerability stops people from answering personal questions.

I put off questions I don't want to answer with a joke.

Last night I mentioned having shoulder surgery. "Was that from a fall?" a man asked.

"Yes," I replied. Silence. I laughed.

"Is Claire there?" her friends asked on the phone. "Yes," I replied. Silence.

"Mom! Stop torturing my friends!"


I've been on date sites off and on for years. First thing to notice is they don't bother to learn your name, sweetheart, honey, dear--those are your new names. Some copy/paste one letter of thought they created to every woman they're writing to without actually reading what you write and don't particularly care. Also a lot of times your questions will be answered in one sentence no matter how "deep" it is. Most you'll get for a starter conversation is "hi". Good luck with that!!
I would LOVE to get a well thought out response after I write a paragraph of stuff. If they do one sentence.

If you mean IRL I would ask what books they read, favorite movies, what kind of art do they like, those are questions that can bring on longer responses. Life of Pi is a great movie and a lot of conversation can come of that.

OMG...I REALLY believe you are right about people not reading what you write to them...and then responding either with something that has NOTHING to do with what you wrote to them...or just basically nothing at all. I am a person who LOVES deep conversations...but...if I don't say a persons name over and over again til they are sick of hearing it...I AM BAD with names...OMG. But...I'm not into any of those names that you put up there...I'd rather'm sorry...WHAT is your name again...I don't know that's just me. LOL...seems you and I have met some of the same people. But...yup, the same kind of stuff irks me as well...i really LOVE a good thought-provoking conversation about...anything. My favorite movie USED to be Casablanca...but I have seen SOOOO MANY movies since then...I forget the movies I deemed almost equal to it. LOL...I guess I need to start paying attention to my own thoughts, lol.

I so get the online thing, that was not what I was lloking for. I updated my post and yes this is for in person with people you already know. Loved, Life of Pi, have had many great conversations with my daughters about both the book and movie on whether it was animals or hurmans he was in the boat with. Thanks for replying.


I always want to get to know the foundational assumptions of a person’s worldview, and whether they can articulate them. But I generally find that people are most often “running on automatic” and are mostly unconscious of their own worldview. That doesn’t mean they don’t have one, but that it’s not something they’ve brought into full consciousness. They usually know some surface “positions” like if they believe in God or which way they lean politically, but if you ask why... the answer is all too often no deeper than “because it’s right!”

skado Level 9 Sep 2, 2019

most people just like to stay there as it doesnt seam scary. living a lie.

@Ms_McSteven very true we humans are scary fucking fucked up rulers of this planet

@Ms_McSteven HAHA, I do not want to start a fight. I will say I do ask this when meeting someone that may become a lover. I want to know if they voted for trump or support this GOP, if so, I am done. I havd an old friend who wanted to become FWB ask me why I asked this and does it mater, my reply, "It does to me, I will not fuck someone who voted for trump, I do have standards."

@Mermaidfantasy whats your problem with me? just curious.

@LeighShelton Not sure if you are asking me something or if this what your question would be. If it was a question to me, I have no problem with you or anyone else on here. My haha was to mcsteven's question on ask who they voted for, and the I do not want to start a fight.

@Mermaidfantasy no i don't want to fight and i fucking hate trump so much and i live in the UK. i don't vote for anyone as there all self serving fucking pricks but if i lived there i would vote just to get that dangerous fucker out of the position of power for sure. My first question still stands and yes its for you my dear. it just seamed like you were bypassing me is all. i just wondered what i may have done but its ok as i havnt lol.

hmmmmmmmm great question. i feel the same. i hate shallow fake shit. what if you could only choose one thing is the one comfert you get from another human being would you just have to keep? or maybe realistically a few and don't think i mean just sex though obviously it can be. i will happily answer the very same question and any question you would like to ask.

one of the most important things to me is honesty, sarcasm and interesting conversations and im happy to talk about anything mostly. remember im dyslexic and my grammer isnt very good really. i actually hate writing as im a way more understandable talker than writer. im really glad i have a keyboard because my writing looks like a 3 year old did it badly.anyway i look forward to your answer xxx

@LeighShelton Your question, let me make sure I understand it, If I had to choose just one thing that would be my comfort from another human being, is that correct?
Answer, that would all depend on if that other human was my mate, family or friend. Mate, it would not be sex but spooning, if family or frinds, long tight hugs. I can give myself sex.
In any relationship, mate, family or friend honesty, integrity and a good sense of humor are the most important things for me and scarcasm is a type of humor.

@Mermaidfantasy perfect answer and you can hug your mate too in good or bad times. In fact a hug can mean quite a few things and you know which one without a word said. The language of touch in fact. Sarcasm that's funny to me shows just how in tune you are and also when your taking the piss etc. Eye contact is really important. You can tell so much by eyes too. Especially lies or love or hate. We have so much communication we often don't even know we are using. In life it's really important to be on the same page even with different interests. Just a glancing touch at the right time can change everything. I love being completely open with people though many don't reciprocate and that's what's so gratifying about a good deep conversation. There's nothing much better and it can be the beginning of so much xx


Some thoughts;
Goals,where do you see yourself in 5 years? 10? or 20?. We all have idiosyncracies that make us who we are,habits,urges and desires.

I asked this only once. I was met by the response "I am here to meet someone for a meaningful relationship, NOT a job interview"

Never asked anyone that again.


Does the left hand REALLY know what the right hand did/ does/ is about to do? What is the why,of the now, of the how,of the wow, of the inside, of the outside, of the internal, of the infernal, of the carnal depths? (How's that?).


Having a conversation with a younger couple last week, I mentioned there were probably 6 bad decisions that I regretted making in my life. It was really an off hand, unthinking comment.

They both wanted to know what they were!!! I took the 5th as I was unprepared to answer!
Then I went home home and made a list ( #6 was squeezed in. Should have stopped at 5)

After continuing to think about it, I realized that I should also focus on the positive and the good decisions I have made

twill Level 7 Sep 2, 2019

@Winkiedink54 I was actually gonna make a post. Wasn't sure how interested anyone would be, or if it would spark a conversation.

Anyway, I'll give you 2 bad decisions 1) Marrying my 1st wife 2) Not working hard enough to save 2nd marriage. ( 2nd wife started acting like the first.....I'm outta here!)


What are the categories? Knowing that could help suggest the questions.

Relationships, Family, Gereral, Friendship, sexual. That is all I have for now, open to suggestions.

@Mermaidfantasy Questions for consideration. What is the longest relationship you've had and why did it end. What made the relationship last a long time. What do you first look at (literally or figuratively) in deciding to like or not like someone. What separates a friend from a lover, same sex or anything else. What turns you off really fast when meeting someone for the first time. Do you have hobbies that no one is aware of. What art do you like and why., How do you exercise your body, or your mind. Do you like any particular breed of dog, which and why. If you saw someone mistreat an animal what would you do. If you saw someone hitting a child in a cruel way what would you do and do you think you could change the life of the child by doing anything. If you were driving on a highway and saw a lost dog what would you do. Where would you bring it if you stop to get it. Have you ever been with someone at the end of their life and what sort of involvement did you have. Does death scare you enough that if someone you knew were dx'd with something fatal would you see the person or avoid seeing the person. How would you feel if you never saw them again. Help you out any?

@K9Kohle789 Yep some great one and a bunch I already thought of. Thank you for erplying.


it can't always happen that way. when you first meet people they don't know who you are any better than you know who they are. they may not want to engage in big talk until you've had your small talk test, as it were. but small talk doesn't have to be tiny. if you're encountering people in a variety of situations, let the situations guide you instead of a prepared list.

oh, and in response to an earlier response you got, someone's not feeling like getting into deep conversations with you does not mean they're living a lie. it means they don't feel like getting into deep conversations with you.

now, as for games with people you already know, however little or well, that's different. games are cool. i wouldn't make the questions overtly heavy. for example, "is god dead?" is not a good conversation -starter. you can learn a lot more about a person from, say "are you a dog or cat person and why?" (it's the WHY that's telling.) that may sound like small talk but it's not. remember, you're playing a game. games can be revealing but they have to be fun or they're not games.


Thanks for replying. I am great at small talk, I work in retail sales, but what I sell ( sex toys) I need to be able to make people feel comfortable and at ease very fast. I have a few friends, who like me, love deep conversations and we can talk for hours together, I wanted to make a game to play with a mix of different people in my life.


How do you feel about us being in a relationship?


What did god do in his spare time, before he made the earth and everything?

I like to gain a feel for the person, to see who they really are. Observation is a key to this. This cannot really be done online as we cannot truly know who is there.
As you get to know another person, I believe you should introduce a little conflict, this allows you all to find where not to tread and where to you can compromise. Firstly of course, find common ground.
But to begin with, talk about your or their family history including them. Introduce some leading questions.


What was the most profound thing you learned as a teenager? Have you ever had dinner in a foreign country? Do you have any phobias? Then again subject matter can apply so the situation art, music, writings, history, etc.


I'm a traveler so I like to know if they like to travel and how they travel. I ask them if they got stopped on the street and were told they could go anywhere in the world they wanted to right now, where would they go. I asked them what kind of places they normally stay in when they go on vacation. This tells me a lot about who they are. Do they need expensive accommodations? Do they like to deal with the locals? Do they check luggage? Are they spontaneous?

Pretty much anything you're interested in you can craft some questions around. To see if they are interested in the same things and how they go about it. Asking them what their favorite class in school was, how they decided to be what they ended up being will give you a little bit about their thought process.

Good luck

lerlo Level 8 Sep 2, 2019

I have no idea. I don't understand when folks say they are no good at small talk. What defines small talk. I have no desire to have nothing but deep meaningful conversations. It always sounds as if it would be humorless, and for me that would be awful. It seems to me when you first meet someone general conversation can tell you a lot. If there is any connection the more important subjects will pop up and flow more easily. What do you consider small talk?

I have a great sense of humor, this is for a game I am making to play with people you already know, to get to know on a deeper level.


What is the very nature of truth, goodness, beauty, and wisdom?


Damn good question but needs a long conversation

0're really not talking about A are talking about a conversation. One thing you might want to the 'I Ching'. I know...a LOT of folks are not into it. But...if you ask it an HONEST WILL give you an honest answer. Maybe you your close friend could talk about the answer that came out. But some might not want to. You will DEFINITELY get some deep thought provoking material though. And yes it will absolutely show you how each person thinks. Some people may not understand the answer...but...if you read it openly...and bear your question in will definitely have some conversations there.


Your great question to all here is a fine beginning which causes me to muse in mirth......1st a friend would not be my lover so my question to any of them would be respectful encouraging ...let me think on that....2nd my family is 2 sisters, a brother, 2 daughters and 2 son in laws and my question would be respectful encouraging based upon our shared knowledge of ourselves not very probing or intriguing.....3rd is an awesome opportunity for lovers and life partners to affirm the tender joys and vigourous joining beyond our trusting satisfactions towards true inner peace of being....such is the stuff of intimacy growing our vocabularies of sentience and habit has been speaking in movie metaphors.....since I am not there with you basking in your aura of desire, I shall retreat a tiny step and invite you to consider Peter Sellers BEING THERE with Shirley MacLaine married to the World's RICHEST dying man.....almost every scene in the film is an example of how language ASSUMES the identity of personality IN THE MOMENT....


hmmmmmmmm great question. i feel the same. i hate shallow fake shit. what if you could only choose one thing is the one comfert you get from another human being would you just have to keep? or maybe realistically a few and don't think i mean sex though obviously it can be. i will happily answer the very same question and any question you would like to ask.

my question is a very deep question. it just might seam a bit shallow at first glance maybe or you don't like me which is fine or you cherry pick the anaswers that suite you. i can take it honest.

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