So, um, do you like....stuff?
October 25, 2011 1:27 PM   Subscribe

What are some questions I can ask new dating partners to get to know them beyond a superficial level?

I tend to be attracted to men who are emotionally unavailable, and I can fairly be described as the female version of that trait. If anything, it's the men who end up commenting that I don't share much about myself. I've described my dating life to a therapist who commented that the conversations are rather juvenile and superficial, i.e. they never really get deeper than "So what did you do today?"

I find that when I hang out with dating partners, I avoid activities that would involve much conversation after the first few dates because I simply don't know what to say (i.e. the relationship comes to revolve around sex and movies). Well, I suppose you could say that initial dates are allowed to be superficial because over-sharing is something to be careful of at this point. I'm great at "getting to know about your family and interests" sorts of conversation, but the more I hang out with a guy, the more stumped for conversation I become. I grew up in a family where we didn't share much about our inner lives and I think that's carried over to my relationships--that part of my brain hasn't really developed I guess, or at least is still struggling to figure out the social norms around this area.

I would like to start breaking this habit. One thing I realized is that I don't really know what kinds of questions to ask that would encourage deeper conversation.

Can you guys suggest questions or lines of conversation that could help steer a dating relationship in a more substantial direction? Things like, "Tell me something about you that I don't know yet." I feel like I need to keep a card in my back pocket so I know what to say on date 4 and beyond that would prevent the relationship from stagnating emotionally.

Thanks in advance :)
posted by oceanview to Human Relations (23 answers total) 58 users marked this as a favorite
but the more I hang out with a guy, the more stumped for conversation I become.

When you find the right guy, you won't be stumped for conversation.

Your question "tell me something about you that I don't know yet" is excellent. I sometimes go along the lines of "what are your values? What's deeply important to you in life?" And that starts us talking about family or the environment or other deep topics.
posted by Melismata at 1:31 PM on October 25, 2011 [2 favorites]

F.O.R.D. Ask about his Family, Occupation, Recreation, and Dreams.
posted by John Cohen at 1:34 PM on October 25, 2011 [5 favorites]

Lots of people aren't good matches, so the conversation hits a wall. Either date more people until you find someone you're more compatible with, or screen for and talk about mutual things of interest before or on the first date. If you don't have a good conversation by date two, then move on to the next person.
posted by zippy at 1:35 PM on October 25, 2011 [1 favorite]

Response by poster: Thanks for the suggestions so far.

I need to point out that I think this is definitely a matter of me not knowing what to say, more so than needing to meet more people. Even when I meet someone who I get along fabulously with and end up dating for months, I'm still horrible at taking things to a deeper level.

SO, I definitely don't think it's a matter of dating more people until i find a better match as I have dated A LOT. I've gone on at least one date with over 50 men in the last couple of years alone.
posted by oceanview at 1:43 PM on October 25, 2011

"Did your family have any interesting *Halloween* traditions when you were growing up?" Replace *Halloween* with whichever holiday is coming up.
posted by arcticwoman at 2:05 PM on October 25, 2011

"Why" is the ultimate conversation deepener.

You: What did you do on Saturday?

Him: I went fishing with Bob

You: Did you like it?

Him: Nah.

You: Why?

Him: All he does is talk about how rich he is.

You: Get out! Why do you think he does that?

. . . .
posted by ferdydurke at 2:05 PM on October 25, 2011 [15 favorites]

I need to point out that I think this is definitely a matter of me not knowing what to say, more so than needing to meet more people. Even when I meet someone who I get along fabulously with and end up dating for months, I'm still horrible at taking things to a deeper level.

How are you in non-dating conversations? If those work well, then perhaps pretend to yourself that you're not on a date in order to have that kind of conversation?
posted by zippy at 2:12 PM on October 25, 2011

Best answer: Rather than spend your time worrying about what questions to ask, why don't you just talk? Literally, just talk about anything: talk about things that interest you, talk about things you hate, whatever; just don't shut up. That's basically what makes up a conversation.

Now, if you find that you're dominating the conversation, then one of two things is going on: you're not compatible, in that he is either socially inept or just doesn't care; or, you are a genuinely boring person.

Seriously though, you get to know people by talking to them, not by playing question and answer; and regardless of what you may think, if you really do need to ask question after question to keep a date going, then you're just not going out with the right people.
posted by lobbyist at 2:16 PM on October 25, 2011 [4 favorites]

OK Cupid blog has a post about this, in the context of questions that correlate well to some other trait or belief.

And in fact, all of their blog posts were immensely helpful in reminding myself that I am not crazy during my most recent rush of first dates.

(Take this with a grain of salt, I selected an Okcupid username that makes it clear I love to talk. Love love love it.)
posted by bilabial at 2:39 PM on October 25, 2011

I don't think you necessarily need to ask more questions, or different ones, for that matter. If you open up, that will most likely urge your date to do the same and your relationship will naturally become deeper. You can't make someone open up when you're not doing the same, right?

I grew up in a family where we didn't share much about our inner lives

So, you have an inner life that you're not used to sharing. Try sharing some of it and see what happens. As far as social norms, who knows? There are people who can say extremely personal things and make it seem casual, so I think it just depends on how comfortable you are with yourself. But really, If you're not used to sharing much then I highly doubt you would overshoot and come off as too open.
posted by seriousmoonlight at 2:48 PM on October 25, 2011

Try to target their fears (or share yours). There's a reason why activities like scary movies or rollercoaster rides are good for dates. They create a bond.

For instance, I bite peanut M&Ms open before I eat them because I don't want to eat a bug. I don't like hidden food. This sounds silly except I did end up eating some infested pistachios, and it was gross and I am pretty much done with pistachios for life. So I could bring this up and ask him about his food fears, or ask him to tell a gross story that happened to him, etc.

Sometimes people's fears are silly - sometimes silly fears can say more about them than they realize. Sometimes another person's perspective and care is very theraputic. And the darkest fears are held very close to our hearts.
posted by griselda at 3:06 PM on October 25, 2011 [1 favorite]

Best answer: I don't think there's so much a secret code you crack to get to someone's inner life so much as asking questions that allow you or your date to add more and more color to the facts. The family and interests conversation you have on that first date is literally just "who" and "what." But there's so much more there, and many of the conversations you have, both as you're getting to know each other and the future if you stay together, are enriched layers of that. The "family and interests" conversation is essentially one that you and whoever you date seriously are going to be having for a long time, in different iterations!

When I was dating, and now with my husband, I love asking questions about growing up. I grew up in a family where we didn't really talk about our inner lives either, but lots of little moments about things we lived through add up to a rich picture of we are, who influenced us, how we used to see the world and how we've come to view our surroundings today.

You know a guy has two sisters and his parents divorced when he was in college and his dad sold medical devices. But do you know if he went on family trips when he was young? To the same place every summer, or a different place each time? Who did he get along with best? Is his father a born salesman, did he wish his children did what he did? Did he have a pet that he still misses to this day? Did he and his sisters ever share a room? Was that a total disaster because he's the neat one? What did they eat for dinner most nights, and is there a dish he still thinks about fondly? Who was the funny one in the family, what did they talk about at the dinner table? Did he like school, or obsess over grades, or go through a crazy baseball card phase until he realized it was pointless because there's too much in the world to collect? Was he allowed to watch unlimited TV growing up? Who turned him onto music or movies or hiking? What did he used to want to be when he grew up? Did he have a favorite teacher who taught him to ignore his critics? Who was his first crush and did he tell her he liked her or did he throw pens at her because he didn't know how else to talk to her? Did he know what he wanted to major in right away in college, or did he flail around for awhile trying things out?

You don't have to ask these kinds of questions all at once - but don't check off the "family and interests" conversation after the first date. There's so much there to explore each time, piece by colorful piece that add up a deeper understanding of who you're having dinner and a movie with.
posted by sestaaak at 3:21 PM on October 25, 2011 [18 favorites]

Here's another vote for religion and politics. Besides, if you disagree fundamentally on these, it's good to know that up front. Also "why" questions in general: "Why did you move here?" "Why did you study taxidermy?" etc. etc.
posted by ceiba at 4:05 PM on October 25, 2011

I haven't done this, but I saw a suggestion recently (for building community) to ask people: "What value of yours would you like to see more of in the world?"
posted by needs more cowbell at 4:25 PM on October 25, 2011

"Why" is the ultimate conversation deepener.

I read this this morning and have been smacking my forehead all day. How, in 25 years, has this solution never occurred to me? Thank you for undoubtedly improving my conversation skills.
posted by gregoryg at 4:41 PM on October 25, 2011 [5 favorites]

I used to use these (from an the old CBC Radio show Richardson's Roundup hosted by Bill Richardson). It served me well.

1. If you could live inside someone else for a day who would that be and why?
2. What makes your heart miss a beat?
3. What do you believe will bring you bad luck?
4. What is the worst insult?
5. If you had all the Lego's in the world what would you build?
6. What do you wear to bed?
7. If you could live in a painting, which one would you choose?
8. If you could be any age again, what age would you be and why?
9. What song you would like played at your funeral?
10. Would you date yourself?
11. Which would you rather win? Why?
An Oscar
An Emmy
A Tony
A Pulitzer Prize
A Nobel Prize
An Olympic Medal
The Stanley Cup
12. What is the beat of your drummer?
posted by sadtomato at 5:33 PM on October 25, 2011 [5 favorites]

As for conversation starters ..."Why" is my least favorite question. It demands explanation when often description is more in order and is more illuminating. "Why" can make people feel interrogated, like they have to justify themselves and the choices they have made. Besides, Why is usually the intellectualization that comes at the tail of all sorts of interesting emotions and experiences. It's reading the analysis of a breathtaking painting before you actually see the painting.

If inner world stuff is what you're after, What is more useful. What was it like for you growing up in a house where folks didn't share much about themselves? What was it like for you to be the only boy of five sisters/an only child/raised by a single mom etc etc. Don't ask why someone moved from Kansas to New York, ask about what the transition was like, what they wanted or expected before they arrived verses what they got. Other ideas: What were you like as a kid? What do and don't you like about (whatever it is they studied, work at, read, do for hobbies etc). What is it about your favorite teacher/writer/book/movie/band/figure/friend that grabs you?

How folks answer What questions will often tell you plenty about their values, worldviews, sensibilities, emotional landscapes, and how well they know themselves far more richly than asking "what are your values" and "why do you do international property law?"

And also, listen to seriousmoonlight on this one. Clever questions are fine and all in a job interview, but not on a date. At best they seem a bit contrived, canned and...well, okcupid-y/Cosmo-esque. At worst you're probing to see if your date is willing to do something that, so far, you yourself are not willing to do. It has this "I'll jump if he jumps first" vibe to it.

If you want openness, be open. If you want depth, be willing to risk some vulnerability to get to it. Take copious notes on how they respond. This alone will tell you half of what you need to know.

I suspect this problem has little to do with conversation and more to do with your own capacity to be open and vulnerable. Puzzle this out and you won't need conversation hacks beyond the first four dates.
posted by space_cookie at 5:50 PM on October 25, 2011 [31 favorites]

I think Tina Fey's rules of improvisation from Bossypants is something that might help you. Think of a conversation as something the two of you are creating together, not a call and response where one person has to think of all the questions.
posted by looli at 6:11 PM on October 25, 2011 [6 favorites]

Best answer: I think the answer here is to start sharing more about yourself and your inner life, rather than questions you can ask your dates.

I also disagree with the "why" question. "Why did you like your fishing trip" is hella awkward. "Tell me about your fishing trip," on the other hand -- not awkward.

I also think you should work on this in your friendships, too, and not just dating relationships. If you're having a problem because you're not accustomed to opening up with people and sharing your inner life -- because it's a habit not to and you're out of practice -- then it will help to work on changing this habit and getting practice (and it will lower the stakes of doing this in the dating context).
posted by J. Wilson at 5:06 AM on October 26, 2011 [1 favorite]

I favorited sestaaak and space_cookie's responses, because I agree both that a lot of revelation can come from exploring the "family and interests" area in more depth, and that sharing your own stories without waiting to be asked goes a long way towards building intimacy.

That said, one question that can lead to some fun "getting to know you" conversations is to ask someone what they would name as their Very Mild Superpower (YouTube link). You can find out a lot about a person's quirks, as well as what they think is (or isn't) worth mentioning as a VMS.

Not everyone gets the concept, which is also good information to have about a person's sense of humor, especially on an early date. I went out with a guy not too long ago whose answer to this question was, "I'm really good at math,"* followed by a long, rambling story about obnoxious behavior in high school to shame classmates who struggled with AP Calculus. It made the decision not to go on a second date very, very easy.

*I think anything that could get you a job should automatically be excluded from consideration as a VMS.
posted by Superplin at 7:05 AM on October 26, 2011

I had a rough time in college learning how to talk to my recently-divorced parents separately. My mom was a talked, my dad not so much. I'd call them to share the exact same news and get a response of "how nice! that's great, honey!... ..." and "oh, that sounds great - how long did you stay? who did you go with? do you think you'd want to try it again?" I don't think it had anything to do with level of interest, but more just conversational style. Ask questions, but stay away from broad strokes ("Tell me about X." "It was fine."). You might htink asking journalist type who/what/how/when/where questions isn't deepening the conversation, but it really is. Getting all the facts starts the conversation flowing, primes the mental pump to start making verbal sentences, sets the context (I went to the movies. Movie X with actor Y and Z. On Friday. With A. and her stupid brother. And I hated it. Well, maybe I would've liked it if he hadn't been laughing. Z is pretty awful anyway. But I liked Y.)
You say you're usually limited to "how was your day?" type conversations. That's actually okay, so long as it goes farther than "fine... long, I guess... glad I'm home... how about you?" You have to be willing to share your thoughts and feelings. Not just what happened (day was long) or details of what happened (I had 4 meetings and made no progress toward my deadline) but how you feel (tired, frustrated that my time is getting frittered away in administrative nonsense, worried about deadlines) but how all that fits into a context (well, they're not hard deadlines, everything's really flexible, so I can't justify dropping everything to finish this report - but at this rate I won't be done till X and manager sometimes says "no problem" and then brings it up at the annual review, I'm worried about long-term performance, but not sure what to do about it. I try to work hard but I'm just not very efficient. And I wish I could blame it on their stupid meetings, but I ought to be able to work around that.).
"Oh, my goodness," you think. "That's really personal!!" That's the idea.

On the other hand, if he's not in a mood to talk, asking questions trying to weasel information out of him isn't going to work. That's when your best bet is to talk about you, share things, and see if he feels threatened by the implied emotional attachment, tunes you out, is really interested and asks questions, relaxes and starts talking to you about his inner monologue, ... whatever.

posted by aimedwander at 7:17 AM on October 26, 2011 [1 favorite]

I suggest discussing the question you've posed in this very Ask, or any other question which has a lot of scope for revealing stuff about people's values. Something which you can discuss, that doesn't have an obvious right answer, and could be a bit humorous. For example, asking this Ask has a nice meta element which would make it amusing, at least to someone like me. Doubly amusing since it's on metafilter right now!
posted by larkery at 9:10 AM on October 26, 2011

There aren't a set of questions that will work for every date, you just have to go with the flow.

However if I want to get to know more from a person, I will observer little details like how they dress, what they brought with them, their moods, and make little comments about it, like,"You don't eat your greens too much." and then it will expand to him respond to you about how he never liked vegetable, his mum used to chase him around the house for vegetable... and then you get to talk about food or childhood, then you are already getting to know him.

On the same time, I would share my little secret like "I never watch horror film", hey that's about my fear, taste for movies in one shot, who knows where that will take you.

Basically, if your questions are not taking you anywhere, make comments, because people are more likely to talk about their opinion when they are presented one.
posted by artofgiving at 12:11 AM on November 8, 2011

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