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.

Can you believe this weather?

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?

'"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 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!”

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.

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

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

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.

g

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

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?

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

Damn good question but needs a long conversation

Well...you're really not talking about A question...you are talking about a conversation. One thing you might want to try...is the 'I Ching'. I know...a LOT of folks are not into it. But...if you ask it an HONEST question...it 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 mind...you 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 delight....my 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.