"So, how about them Mets?" sucks. I need awesome questions to spur conversation, create bonds and learn more about people.

August 5, 2007 2:03 PM

What are the best questions you've ever been asked / asked someone to get to know them better, build closer friendships/bonds, find out secrets and interesting tidbits about their lives and worldviews? I'm rather introverted (but working on being more sociable). I really relish meeting and interacting different people with different views but too often conversations aren't very interesting so I'm really not engaged or connecting with them. I'm trying to get a lot better at chatting, learning about people and building bonds with people, but I need more ammo for interesting questions to unlock that higher level of discourse with the people that surround me.

I'm just looking for a way to get better and more interested in having conversations with new people (or newer people), and the normal mundane talk about the weather/sports/jobs is really making that difficult.

All questions suggestions are welcome!

Here's a few examples of the 'target market' type people, I wish I had better questions/conversations/bonds with:
- New friends I just met out at an event
- Potential significant others
- Cool coworkers and people in the community I admire
- Clients, bosses or other networking relationships
- Nice old ladies on the street
- My girlfriend's dad
- Reconnecting with long lost relatives
- The local butcher, the baker, the candlestick maker
- Learning more about close family members (who I think I know everything about already)

(Basically, please don't get pigeonhole any of your suggestions to any one of these targets... I'm just interested in hearing as many of the best questions, ever.)

Btw: Any other tips for an introvert looking to build bonds and have more interesting conversation is welcome! :)

Thanks!

posted by jkl345 to Society & Culture (46 answers total)

I usually start with the normal, mundane stuff and look for that nugget of difference. Then: "[whatever they just told you that you find interesting]? Really? Wow! Can you tell me more about that?" eg. "You just got back from Russia? Really? Wow! Can you tell me more about that?" You can vary the wording ("What's that like?" "How did that happen?") but the sentiment is what you're after.
posted by joannemerriam at 2:11 PM on August 5, 2007 [2 favorites]

"What would you be doing now if you hadn't gotten into X?"
posted by Brian James at 2:23 PM on August 5, 2007 [1 favorite]

I find that asking people about their favorite books or movies tends to reveal a lot about who they are - the trick being to follow up by asking why that particular (book/movie/show) is their favorite. Learning what character someone identifies with, or how a particular story resonated with them often leads them to open up about their life a bit more. People aren't going to skip over idle weather chat and go straight into their deepest secrets. You have to get to know each other, and that's the joy of it.

On an informal level, talking about pop culture items like shows and movies makes a lot of sense - most people feel comfortable talking about these things and don't find questions like these to be too personal for a casual acquaintance to ask. Someone can use their love of say, Star Wars to tell a lot about their personality.

Another good conversation starter is to say you're planning to travel and asking them where their first choice of destination is, where they think you should visit. Someone might tell you about a childhood trip to the Grand Canyon or going to Paris while in university. They might tell you about watching the sun rise over the Atlantic ocean while on a road trip with friends.

Overall I say the secret is in follow-up questions - drawing the other person out and getting them to elaborate on their experiences. Don't ask a question and then expect the other person to take over. Listen carefully and ask lots of subsequent questions, like "Oh, your favorite movie is Dr. Strangelove? Are you a big Kubrick fan? Are there any of his films you don't like? When did you first see that movie?" etc. Don't act like you're writing a biography on them though - be sure to share your own thoughts and experiences as well.
posted by SassHat at 2:25 PM on August 5, 2007 [4 favorites]

The key is being a good listener. Other people are dropping hints all the time about what they really want to talk about. The boorish person doesn't pick up on this. Example:

You: I've heard you guys work long hours at XYZ corp!
Them: Yeah but I try to keep a reasonable work week to save time for my other passions.
You (boorish): So, do you know my friend J.? He works there too.
You (listener): Ah...what are those other passions?
posted by vacapinta at 2:33 PM on August 5, 2007 [11 favorites]

"Who is the most admirable human being of the 20th Century?" It's a question most people have never considered, and so it makes them think.

Being that "admirable" is subjective, the answer to this question will tell you a lot about a individual's values. I've asked this question of literally hundreds of people as a conversation sparker (I am not good at smalltalk either, unless it's about baseball), and I've heard answers ranging from MLK, Ghandi and Mother Theresa to Einstein, Jonas Salk, and Thoreau.

If someone says "Ayn Rand", well... that tells you something about their character. So does "Al Gore", "Theodore Roosevelt" or "Ronald Reagan". So does "my dad/mom/uncle". I've heard all of those and more. Even Yasser Arafat. One person said "Osama bin Laden" (suffice to say, I didn't like what I learned about THAT person's character.) I've also heard "no one is admirable" and an interesting reason for that view.

The most interesting part is the followup question..."why?" What better way to learn what a person values, than to ask them who they admire and why?

[also, the question is best limited to the 20th Century -- for one reason that it should be someone who may have lived/be living in our times and is therefore better understood, and the other big reason is if you don't limit the question to the 20th Century, the answer will be "Jesus" 80% of the time.]
posted by edverb at 2:38 PM on August 5, 2007 [2 favorites]

Would you rather be a ghost or a vampire? A ghost person will tend to be introspective and bookish. A vampire will tend to be more outgoing and impulsive. Even if I'm wrong its always fun to hear their justifications.
posted by damn dirty ape at 2:40 PM on August 5, 2007 [1 favorite]

I like saying "How was your day?"

it doesn't sound unnatural to ask and it's generally pretty easy to answer.. doesn't take a lot of introspection.. opens doors to other questions.. Answering that question tells a lot about where they work or what happened that they want to fix, that they love etc..

It's a doorway to a lot of follow-up..
posted by onanon at 2:41 PM on August 5, 2007 [11 favorites]

If you generally pay attention to the world at large, it’s easier to talk to people from the world at large:

Them: Yes, I am a Sikh, but I grew up in New Dehli, and spoke Punjabi at school and at home.
You: Ah, so do you feel that you’ve much connection to the Punjab of today, or do you consider yourself Indian first and foremost?

Doesn’t always work—actually, in the example I give there, the dude I was talking to seemed to be not too taken with the idea of going into the ethnic and religious details of various regions of the Subcontinent, perhaps understandably, since it is complicated and can take ages to explain—but for most other places they’ll be happy to go into background detail.
posted by Aidan Kehoe at 2:45 PM on August 5, 2007

I always want to know what people are passionate about. Some people aren't passionate about anything, and that's kind of boring. You could be passionate about your work, hobbies, people you know, etc. Even dreams or things you want to accomplish. I just like to see what excites people. If it isn't immediately apparent from conversation, I've been known to simply ask, "So what are you really passionate about?" Some people have a ready answer for this, or can think of something quickly, and some get thrown for a loop. It's interesting to see both what people say and how they react.
posted by autojack at 2:59 PM on August 5, 2007 [2 favorites]

For the elderly, I sometimes ask -- what was it like growing up in [wherever they grew up]? What did you do for fun when you were a teenager? [This one is usually really fun to listen to and follow up on.] What was the first car your family owned? What did your father [mother] do? How did you meet your husband (wife)? Any of these questions, if you listen to the answers, will lead to other questions, and a very interesting conversation. Many older people like to talk about what it was like in "the old days" and I've found that listening to them is sometimes fascinating.
posted by la petite marie at 3:11 PM on August 5, 2007 [2 favorites]

Seconding Aidan, above. Where are you from? Where are your parents from? What's it like being a _____ in _____ ? Would you ever go back to _____ , or do you feel like you are here for good?
posted by Meatbomb at 3:30 PM on August 5, 2007

Ask them for help with something they're knowledgeable about.
posted by futility closet at 3:39 PM on August 5, 2007

The problem is that a lot of probing questions, the ones that sound like they could be part of a quirky online dating profile, will tell you a lot about a person, but will also put the answerer on the spot, making them feel uncomfortable talking to you. If a person I've just met and am just getting to know asks me a question that "makes me think" about which dead person I'd like to have dinner with and why, but also makes me feel like I'm in a weird job interview, I'm going to feel a little put off by that person. You'll glean information about me if you get an answer, but I'm not going to feel closer to you, and I'm probably going to think you're a bit odd for asking me what animal I think I'm most like or what comprises my ideal day.

The best questions are normal, boring ones with good follow up. There are some good suggestions above. Ask about people's hobbies and then take a genuine interest in learning more about the things they're passionate about. Ask what movies they've seen lately and whether they liked them, and then have a general repository of knowledge about books and movies that you can use to have a back-and-forth about stuff you like that you can recommend to them, and vice versa. Ask about their jobs, families, where they bought that fabulous blouse: normal stuff. But then don't let the conversation lapse once they've answered the initial question.

Also, people's childhoods are always a great topic of conversation. Have a good embarrassing story or two from your own adolescence, which will encourage people to start swapping stories of their own funny childhood foibles: instant bonding. If you can open up and be a little self-deprecating, others will follow, and that makes people feel closer to one another. But be careful to keep the tone light; don't dump serious problems on new acquaintances. Stories about throwing up in front of your whole seventh grade class are perfect. Stories about getting beaten up by bullies every day may be too heavy.
posted by decathecting at 4:08 PM on August 5, 2007 [5 favorites]

Dale Carnegie has a tried, true formula for this. Where are you from, what do you do, &c. His and similar methods all work if you listen to the other person and allocate no mind space towards any other subject besides what they are saying right now. Key point: a hundred percent attention.

Today I talked to a preacher for five minutes and he could not listen to what I was saying. It isn't that easy is what I'm saying. That is practically his job.
posted by bukvich at 4:37 PM on August 5, 2007 [1 favorite]

OK I googled 'em up:

Where are you from originally?

What brought you here? (If not from here)
Have you lived here all your life? (If from here)

Do you have a family?

What do you do?

What did you want to be when you were growing up?

You maybe could start a fascinating metatalk chatfilter post with these. . .
posted by bukvich at 4:45 PM on August 5, 2007 [1 favorite]

I had a lot of great unexpected conversations at a high school reunion last night with questions along the lines of 'what would you like to be doing?' The key is always to make the person feel like you are interested in them in a way that shows you are not just sizing them up as people often feel when hit with "so what do you do?" questions.
posted by Space Coyote at 4:46 PM on August 5, 2007 [1 favorite]

Ask the questions you want people to ask you.
posted by Ironmouth at 5:14 PM on August 5, 2007 [5 favorites]

decathecting is spot-on: don't go with the 'profound' questions, at least not immediately. Most people want desperately to talk about something, so it's just a matter of finding simple, open-ended queries that set that off. There aren't really good standard ones simply because any standard ones are used a lot, and often come across as annoying or transparent. "How's it going?", "What's new?", and the like work because they're unobtrusive and let people get to the real topics they want to talk about.

As an example, my fiance is American, so as soon as people hear her accent they ask about being an American in NZ, and how she likes it here, and what she thinks of Bush, and so forth. She's been asked these so often that it feels like her own personality has been subsumed by her status as The American. An accent is an obvious 'in', but not the best one in this circumstance.
posted by Paragon at 5:15 PM on August 5, 2007 [1 favorite]

Oh, man, I hate "what did your father do?" "what would you have been doing if you weren't doing your current job?" and all similar questions. They seem invasive and make me feel like I'm getting a rote grilling at a job interview. Maybe some people like those questions; they offend me, personally, because they're pushy, and they will always get a jokey, glib response. And I will be very unimpressed with the person who asked them. YMMV.

I've never been asked anything like "Who is the most admirable human being of the 20th Century?", as suggested above. If I were, it'd be all I could do to stifle a laugh -- it seems like the kind of cack-handed question an 8th grader would ask if given an assignment to "interview" a family member. Plus, there's always a risk of inciting political anger or moral disapproval, unless you give the one single unassailabe answer, "Martin Luther King." So I'd probably laugh, say "Martin Luther King, of course -- and who do you think is the most admirable?" ... and then escape to get a stiff drink at the earliest opportunity.

I don't think there is any set of questions that can be memorized; extremely boorish people will answer anything because they're delighted to have an audience, but anyone with a brain and a shred of sensitivity will detect BS. Instead, tune in to subtleties in their conversation and amplify them. This way, you're taking their lead, and they will be at ease.

--"Well, I met the hostess when we were in the PTA together."
"Really? How old are your kids now?"
--"I hated the Simpsons movie."
"Were you ever a fan of the show?"
--"This is delicious hummus."
"Oh, are you into Middle Eastern food?"
posted by ROTFL at 5:22 PM on August 5, 2007 [6 favorites]

The best question i've ever been asked: You've died and gone to heaven. When you meet God, he says that as your heaven you get to replay one day of your life over and over again like a neverending record. Which day did you chose?


posted by Ugh at 5:49 PM on August 5, 2007 [11 favorites]

I agree with decathecting and Paragon. In fact, I knew someone in school who used to ask people he had just met, "What's your passion?" (pretty much autojack's question). Without fail, it freaked people out as soon as they realized he was serious. It might be very interesting for the asker, but the answerer may feel very put off.

Ask the mundane questions, and find something not mundane in the answers. Then ask about the not mundane thing.

Failing that, I use onanon's "How was your day?", or a variation my friend used, "What's the best thing that happened to you today?" which I find more likely to get a positive answer, even if the day hasn't been great. If you ask how the day was, and it sucked, that's not so great conversation with a new person.

You may find this thread to be helpful too: I'm trying to stop asking, "So what do you do?" What are some more interesting conversation starters? What do they ask or say in your area?
posted by jewishbuddha at 5:53 PM on August 5, 2007 [2 favorites]

Great questions are like great comebacks for me. I think of them later at some point like when I'm brushing my teeth, taking a shower, eating lunch, whatever. I would say that the best things tend to build off of something you already know about a person, but in a kind of strange way. Talking to religious people about their beliefs can be really interesting, but you have to find those magic few who quietly go on believing--the ones who you don't find out about their faith until weeks/months later when you try to plan some Sunday activity and they're like "ehh, I have to go to church."

A question about comfort food can be fun, and can tell you a lot about people and how they grew up.

I tend to dislike the "Why do you do X?" questions because they make me feel weirdly deficient, as I often just really don't know. And hoo boy, when you find the people who think of every semi-private question as an affront . . . and conversations seem to always go exactly nowhere, no matter how hard you try, just stop bothering with them.
posted by that girl at 6:11 PM on August 5, 2007 [1 favorite]

-What were your favorite toys growing up?
-When you're thinking, how do you refer to yourself, like if you were hungry would you think, "I'm hungry" or "You're hungry" or something else entirely?
-When you close your eyes and imagine, say, a car, can you visualize a car in your mind's eye or do you just understand you're thinking about a car?
-What language do you think in?
-Can you hear your inner monologue inside your head as if someone was talking out loud, or is it just silence?
posted by knowles at 6:24 PM on August 5, 2007 [6 favorites]

ROTFL, when faced with a person who puts everything down, I don't bother to venture a revealing question. If forced by circumstances to converse with them at all, I'll resort to empty slambook conversation about the latest movie or their favorite foods, as you suggest. All the while I'll smile and nod, bored to tears, and will myself escape to get a stiff drink at the earliest opportunity.

So, it works both ways. People who regard innocuous attempts to spark an interesting conversation as if they were being cross-examined aren't worth the effort. Guarded people aren't likely to engage in a "higher level of discourse" as posed in the question. Besides, it's far more enjoyable to converse with people who aren't looking for reasons not to converse.
posted by edverb at 6:55 PM on August 5, 2007 [1 favorite]

I posted this elsewhere, but it's appropriate here too:

I try to ask my elders who've seen and done considerably more than I have: "I'm 29 now. If you could, what do you know now that you would tell yourself at my age?"

It offers some insight into what is important to them now and also just plain offers some insight.
posted by drinkspiller at 7:28 PM on August 5, 2007 [3 favorites]

Once I know what someone does, I like to ask them about the most interesting thing they've ever done as a part of their job. Like, I asked my dental hygienist what mouth was the worst she'd ever worked on. (A middle aged guy from Vietnam who'd never been to a dentist in his life. It took four visits to get his teeth clean.) Or I'd ask someone who works in a call center about the weirdest call he'd ever gotten. I like these types of questions because they're not too personal but everyone has a war story.
posted by sugarfish at 8:18 PM on August 5, 2007 [1 favorite]

nthing decathecting.

As much as smalltalk sucks (doesn't everybody hate it?) sophomoric armchair psychologists asking questions "that sound like they could be part of a quirky online dating profile" suck even more.

If taken with a grain of salt, perhaps treated as a bit of a parlour game between existing friends, then they can be amusing enough, but asked by strangers they're actually quite confronting. The answerer typically wants to create a favourable first impression, and it's hard not to feel like you're being put under a microscope when trying to respond to something you might never have given a second's thought to, like "what would be the first three laws you'd pass if elected President?".

If you think about it, any adult has lived for long enough to have accumulated a rich personal history, which is likely to be quite different in most of its detail from your life. There's plenty of interesting information to find there, without resorting to clever riddles & hypotheticals.
posted by UbuRoivas at 9:19 PM on August 5, 2007 [4 favorites]

Let me just add that I think the advice should vary considerably depending on whether you know the person already (and have established something of a relationship) or whether the person is essentially a stranger. If someone I didn't know walked up to me at a party and asked what famous person I'd most like to dine with, I'd probably assume that they were being ironic and become interested, but otherwise might react like decathecting or ROTFL.

Edverb, I understand your reaction to ROTFL, but I don't think you can chalk it up to an interest in putting everything down.

In my view, the key to conversation isn't just listening to people -- if you ask them to speak to a topic that's forced, they may literally be speaking, and you may literally be listening, but they're not controlling the expression. I think it's interacting with them in a way that makes them feel like you are interested in them and sense their special qualities. So if you ask them a generic question, you're showing that you want to talk to them, but little more -- you're also asking the same thing you'd ask the person next to them, or a ham loaf. Perhaps it'll get things started, but in my view on a bad footing.
posted by Clyde Mnestra at 9:40 PM on August 5, 2007 [3 favorites]

-Can you hear your inner monologue inside your head as if someone was talking out loud, or is it just silence?

If you ask this, be prepared to hear: "Crickets, actually."
posted by Clyde Mnestra at 9:45 PM on August 5, 2007 [1 favorite]

Here is a great article I recently read on being a good conversationalist. It could be required reading at school.

http://www.economist.com/printedition/displayStory.cfm?story_id=8345491&fsrc=RSS
posted by snowjoe at 10:13 PM on August 5, 2007 [4 favorites]

Don't ask people to tell you about things in their life, ask them to tell you how it feels to be them:

- "I'm a lawyer"
- "Do you enjoy your job?"

- "I live in Brooklyn"
- "Do you like living there?"

- "I have two kids"
- "Do you like being a father?"

You'd be surprised, but most people don't have a canned answer for that. Some people are so used to explaining their lives in an impersonal, smalltalk way that they actually have to stop for a few seconds to think about the question. If they do have a canned answer ("Yes! Being a lawyer is the best job in the world!"), you can ask them what they like about it.
posted by fuzz at 2:54 AM on August 6, 2007 [14 favorites]

Here's a thing I started doing with my two teenage daughters ... teenagers in general being famously closed to conversations with the parental units. Instead of just asking, "How was school, or your day, or work ...", I ask them, "What was the worst thing that happened today and what was the best thing?" The worst thing brings out a war story and gets them talking about their worries. The best thing tempers the bad stuff and reminds them that there's always something good. I tried this with a few adults and it seems to work there, too. I think it's a deeper question than usual, but by keeping the question to a one-day time frame, it's somehow less creepy. Just a thought.
posted by lpsguy at 6:46 AM on August 6, 2007 [11 favorites]

The three questions I ask everybody I meet in order to decide if I can love them:

1. Let us assume you met a rudimentary magician. Let us assume he can do five simple tricks -- he can pull a rabbit out of his hat, he can make a coin disappear, he can turn the ace of spades into the Joker card, and two others in a similar vein. These are his only tricks and he can't learn any more; he can only do these five. HOWEVER, it turns out he's doing these five tricks with real magic. It's not an illusion; he can actually conjure the bunny out of the ether and he can move the coin through space. He's legitimately magical, but extremely limited in scope and influence.
Would this person be more impressive than Albert Einstein?

2. Let us assume that a fully grown, completely healthy Clydesdale horse has his hooves shackled to the ground while his head is held in place with thick rope. He is conscious and standing upright, but completely immobile. And let us assume that --- for some reason -- every political prisoner on earth (as cited by Amnesty International) will be released from captivity if you can kick this horse to death in less than twenty minutes. You are allowed to wear steel-toed boots.
Would you attempt to do this?

3. Let us assume that there are two boxes on a table. In one box, there is a relatively normal turtle; in other, Adolf Hitler's skull. You have to select one of these items for your home. If you select the turtle, you can't give it away and you have to keep it alive for two years; if either of these parameters are not met, you will be fined $999 by the state. If you select Hitler's skull, you are required to display it in a semi-prominent location in your living room for the same amount of time, although you will be paid a stipend of $120 per month for doing so. Display of the skull must be apolitical.
Which option do you select?

- Chuck Klosterman
posted by ND¢ at 7:21 AM on August 6, 2007 [4 favorites]

Lots of answers to the above questions from various mefites found in this thread (when I quoted them last time).
posted by ND¢ at 7:23 AM on August 6, 2007 [1 favorite]

The best conversationalist I've met always used "How'd you learn to do that?" Works in all sorts of situations.
posted by MrMoonPie at 7:40 AM on August 6, 2007 [11 favorites]

Yep, I agree with decathecting as well. It's not that the deep questions are BAD questions, but it's not what I generally want to talk about when meeting people at a bar or whatever. In these situations, I don't want to have to sit and think for too long, knowing my answer is going to be judged.

I'm a HUGE fan of "How was your day?" If you want to get more into detail, ask them what they did. While many would answer the first question with "fine", asking them WHAT they did could lead to many follow-up questions...you could off track before they even got to the afternoon!

You could also try silly questions like, "Would you rather be invisible or able to fly?" This isn't as intimidating as some of the other ones, and people usually come up with pretty interesting reasoning.
posted by jetskiaccidents at 8:29 AM on August 6, 2007

i was on jury duty one year and spent an inordinate amount of time in the jury room with people i barely knew with instruction not to talk about the only thing we had in common.

one guy continually posed us all questions to keep us entertained. what were you doing when the space shuttle blew up? where were you when reagan was shot? who was the best teacher you ever had and why? where do you like to go on vacation? what is the weirdest food you have ever eaten?

easy to answer, not too intrusive and with a little effort they can lead into deeper conversation.
posted by domino at 8:36 AM on August 6, 2007 [1 favorite]

There was a website that claimed that there were only two things that anyone needed to know about anything. "So you're an [engineer]? What are the two most important things about being an [engineer]?" "You canoe whitewater? What two things would you tell people about this?" etc.
posted by Chuckles McLaughy du Haha, the depressed clown at 9:28 AM on August 6, 2007

I always find that talking about recent vacations or asking where a person would go on vacation if they could go anywhere and why is always a good conversation starter. People love talking about vacations.

Also, make sure that the conversation is a back and forth. I know people who are almost agressive about asking questions to the point where I cannot ask a question of my own or get them to talk about themselves. It can feel like a competition - Who can show more of an interest in the other person?!? - and even if it doesn't feel that way, it's frustrating for me as it basically becomes a one-sided conversation. I think while you are asking the other person questions, you should slip in little bits of info about yourself. An example:

Other person: "I just returned from Amsterdam"
You: "I've been there too! I think the Van Gogh museum was my favorite part. What was yours?"

Kind of a lame example, but the point is that you are giving a bit of information about yourself should they want to ask you something, second you are establishing rapport - you have something in common! If they don't ask you any follow-up questions about yourself, then you know that this is going to be more of a "listening" conversation for you, which is fine. But if the person wishes to ask you something about yourself, they have a chance. I really think that establishing friendly and close relationships is being able to maintain a back and forth sort of thing like this as much as possible.

Another important thing is to remember to ask after things that a person told you next time you see them:

You: "Hi Jack. Last time I saw you, you mentioned that you are trying to sell your house. How is that coming along?"

You will soon enough be able to sense what a person likes to talk about and what bores them and you'll get a better idea of how to act. Good luck!
posted by triggerfinger at 10:54 AM on August 6, 2007 [1 favorite]

If I'm talking to someone I've just met and want to know more about them I ask: "What are you passionate about?!"

This is very effective and letting people take the conversation where they want, to a place that they're enthusiastic about. When you see someone's eyes light up when they're talking about something they love you get a great sense of a person. No two people have ever given me the same answer.

For the very small subset of the population that is stumped by this question, well, that's a great flag that they're not somebody I'll be seeking to spend time with in the future.
posted by donovan at 2:01 PM on August 6, 2007

Whatever you do, don't ask people what they do, i.e. what they do for a living. You might get "circus lion trainer," but its much more likely you're going to get "accountant," to which you will (quite naturally) respond: "Hmph."

Ask people about what they love.

Ask them what thrills them. Ask them where they would go if they could go anywhere. Ask them who they would spend a day with if they could spend one with anyone. Ask them what one thing they'd want with them if they were stuck on a desert island. Ask them what kind of books they read. Ask them about their favorite types of art.

Ask people what scares them.

Ask them if they would rather be more rich or more smart. Ask them if they think they're above average. Ask them what they think will happen when they die. Ask them how they would choose to die, if they could. Ask them what they would hope would be on their tombstone. Ask them if they think we are alone in the cosmos.

Ask them what they couldn't live without. Ask them about their pet peeves. Ask them about the person they wish they could be (but be sure to ask them if they're happy with who they are). Ask them what they think they are best at. Ask people about what they've done, sure, but more importantly, ask them about what they hope to do.

Follow up every single one of the above questions with: "Why?"

And, when all else fails...

"So...pirates, or ninjas?"

or its popular variant, bears vs. monkeys.
posted by allkindsoftime at 2:46 PM on August 6, 2007 [4 favorites]

Seconding two suggestions above:

"What's the best & worst thing about X?"

"What are the two most important things to understand about X?"

eg Whatever you do, don't why not ask people what they do, i.e. what they do for a living. You might get "circus lion trainer," but its much more likely you're going to get "accountant," to which you will (quite naturally) respond: "Hmph." with one of the formulas above. It's a kind of question that people have not necessarily considered before, so it's a bit of a thought-provoker, but you're playing to their expertise (because you're talking about their job / hometown / favourite travel destination / favourite movie, etc) so they *are* in a position to answer intelligently, and you never know what you might learn...

"Worst thing about being an accountant? Well, what the fuck do you imagine? It's often dry & tedious, with long hours, I have to hang out with uptight suits all the time, and I had to shave off my mohawk & take out my piercings the day I graduated from college. On the other hand, the best thing is that you're exposed to insider knowledge of all kinds of different industries...you wouldn't *believe* the dodgy book-fiddling that happens in the energy sector! Did you know that 90% of energy companies are basically Enrons in the making? (etc)" - now that, to me, would be interesting.
posted by UbuRoivas at 4:04 PM on August 6, 2007

Try "How to Talk to Practically Anybody about Practically Anything," by Barbara Walters. Hope you can get it.
posted by JimN2TAW at 4:16 PM on August 6, 2007 [1 favorite]

In contrast with much of the advice here, I rarely try to start a conversation with a question -- I think that's horribly intrusive. I tend to offer a neutral observation of my own on a relatively drama-free topic, perhaps related to the immediate environment we're in, and acknowledge a range of contrasting opinions about it. From there, most people will pick up and say something, and you can take it from there in the vacapinta style.

If they don't, be careful about the fishing. Many people really hate being put on the spot. If you can amuse such people with some silly chatter of your own, making it clear that nothing's at stake and you aren't hanging on their every word, they'll often relax and start talking themselves.

What's-your-passion interview questions like the ones so many of you are suggesting -- well, I never even used them when I was an interviewer.
posted by tangerine at 8:21 PM on August 7, 2007 [2 favorites]

The purpose of The Rundown is to get out of small talk and into something interesting as quickly as possible. I'm certain I read about this somewhere on MeFi. At any rate, it changed me for the better.
posted by eritain at 12:10 AM on October 28, 2007

I find that if the conversation ever dies down to that awkward silence I'll ask everyone this psych question.

What's your favorite color and list three adjectives why. Remember adjectives are descriptive words, not nouns or phrases.

Try to be cute and funny when you explain what adjectives are. Everyone then goes and does it. When they are done you tell them what it means... the adjectives describe what they think about themselves.

It's really funny to see ppl's reactions. Some have been embarrassed after describing the color as sexy or horny even, but it provides a good laugh.

I don't do it everywhere I go, but every now and then, when I start to feel more comfortable around ppl that I just met, I'll ask it. You'll know if it's a good crowd for it or not.

Also, try not to do it w/ more than 4 or 5 ppl. Otherwise, the convo just moves on to other things.
posted by dannon205 at 5:18 PM on November 23, 2007 [1 favorite]