How to escalate small talk to medium talk?
January 4, 2015 10:30 AM   Subscribe

I met this great guy in NYC on everyone's favorite dating website. We've been out a few weekends in a row and had a great time together, but I'm running in to a sort of roadblock, conversationally. We are both introverted and quiet, and we both find small talk is insanely boring.

I can tell we'd both enjoy talking about deeper subjects, like the human condition or any other antisocial gem, but I literally have no idea how to bring it up. Usually I go for the adorable, "I want to talk about this with you but I don't know how to bring it up" segue, but it's awkward at best. How do I instigate these types of conversations with ease? I'm more interested in how his brain works as opposed to his favorite bar or what his siblings do for a living. Help me, please!
posted by Kestrelxo to Human Relations (16 answers total) 20 users marked this as a favorite
How about a board game or other game that requires some element of thought or creativity? Even a simple or childish game could help break the ice and make you both more relaxed.

You could also play something like "Two Truths and a Lie" (each has to guess which is the others' lie) or answer questions from "The Book of Questions"
posted by bearette at 10:36 AM on January 4, 2015 [2 favorites]

What about talking about movies or books that operate on that level?
posted by roomthreeseventeen at 10:40 AM on January 4, 2015 [3 favorites]

I have no idea if this is good advice or not, but it's advice.

On internet dates, especially once we're past the "so where did you go to college?" basic dossier stuff, I just talk about what I wanna talk about.

I have had a first date where I asked someone whether they would ever engage in cannibalism. And then we dated for five months, broke up for very mutual "this isn't working out" reasons*, and are now good friends.

I have had a first date where I asked someone what the craziest drug they've ever done was. The results weren't quite as promising, but we did date for a while and they didn't run screaming from the room or anything.

Meanwhile most of the times things never progressed past the first couple of dates, it was because I was trying too hard to seem nice and normal and like the kind of person who would go on a date with this guy.

Another thing that is good on early dates is to do an activity together. Go hiking or to a museum. I did one second date in a local board game cafe and we played Ticket To Ride and it was great. These types of dates give you a lot to talk about that isn't yourselves/each other, and also they force you to sort of be on the same team and actively do something, which I think can give you a better sense of how you work together.

*No, I did not try to eat him.
posted by Sara C. at 10:41 AM on January 4, 2015 [10 favorites]

I think the two of you should watch this short film together and then laugh your asses off.
posted by sexyrobot at 10:41 AM on January 4, 2015 [1 favorite]

Best answer: Introducing an element of dialectic (i.e., logical conflict or problem) is good for deepening a conversation, I find. It doesn't have to make things argumentative or fighty-- you can just be on the lookout for interesting intellectual problems in the regular flow of smalltalk, and working through them together frequently leads out to deeper conversations on the Meaning of Things. Thus, for example,

Guy: So yeah, my sister is an X-ray technologist.

You: (spotting topic for shared inquiry): Wow, that's an interesting contrast from [your humanities job]. Is one of you an outlier in the family, or is your whole clan split like that between sciences and arts? [aaand lead into conversation about hereditary similarities among siblings, different cognitive approaches between hard sciences vs. humanities, birth order impact on personality, whatever]

OR: You: That must be so interesting, to be seeing all this healthcare-transition stuff from the inside. Has she talked much about how Obamacare impacts her job? [aaaand lead into conversation (which need not be overly political) about socialized vs. private healthcare impacts on particular professions, the dynamics of new tech in shaping healthcare, etc., etc.]

Basically, don't just trot out smalltalk factoids and let them lie there limply; analyze them, synthesize them, spot patterns, point out problems, bat around ideas and hypotheticals. I can think of very few casual conversation topics that couldn't be pushed out into much deeper waters within an exchange or two.
posted by Bardolph at 10:48 AM on January 4, 2015 [41 favorites]

Take a risk and bring up your own ideas first. "I've been thinking about X in society and how weird/wonderful/confusing it is. I really hate/like how it is now, and I think it would work better if we did Y as a species/country/society instead. What do you think?"

"I read a really interesting article about X, where they said...I'm not sure if I agree, because Y. What do you think?" also works.

These don't have to be (and shouldn't be!) long monologues, just a few sentences giving some context for the idea.
posted by jaguar at 10:50 AM on January 4, 2015

I like to talk about books I'm reading, or interesting stuff I've seen on TV, or news stories.

For example, I'm reading a really interesting book about North Korea right now, and it's a gold mine of conversation.

I'll recommend one of my favorite books that will spur deep conversations as well as help you assess if this guy is on the same page as you are on fundamental things. How to Marry the Man of your Choice. (note: choice, not dreams. ) Yes, the title is awful and it was written in the eighties, so there's some stuff there that may not resonate, but the foundation is solid and it offers conversational starters that provoke real thought and provide thoughtful answers.
posted by Ruthless Bunny at 11:10 AM on January 4, 2015 [2 favorites]

"Why is that?" said in a nice, eager way can work.
posted by michaelh at 11:14 AM on January 4, 2015

At this point, being who I am (an outlier), I'd be all, "On our next date, let's either go to the Museum of Sex or, at least, talk about sex."

I care about sexual compatibility. A lot. YMMV but I would want to know, eventually, if I were dating someone who might be a good fit in matters sexual. Including the ability to laugh while viewing plasticine-made "Grumildos" that are "part kinetic theater, part art installation and part puppet performance."

(How jealous am I that New York has the Museum of Sex and San Francisco does not? So jealous! Um, sorry for the derail.)

If that's skipping from small talk to deep talk too quickly, then I'd simply ask the guy what he cares about. Does he have any passions? If so, what are they?

Not in a girlie, let's focus on him kind of way. Simply to learn more about him by starting the type of conversation going that you prefer. It's a perfectly reasonable question. And then, in turn, you can share some of your own passions.

In short, you want to skip the small talk so skip it. You've done that. Time to cut to the chase. Start asking about what matters to him and talk about what matters to you.

Do it while moving, ideally. There's some science (I bet jaguar knows what it is) that suggests it is easier to have potentially stressful conversations while walking side by side instead of facing each other across a cafe table.

Also, just personally, I hate the cliched coffee date. All my first (and 2nd) dates are walks in parks (cause public!), bowling, playing pool, going to museum, etc. So nthing the suggestions above about doing an activity together.

Don't be afraid to ask meaningful questions now. You are not obligated to stay in Small Talk World. In fact, you can be direct and say, "Small talk is not much fun for me. Mind if we have some meatier conversation?" Then see what happens.

And, because you are not me, perhaps skip the sex museum idea for now--or forever.
posted by Bella Donna at 11:16 AM on January 4, 2015 [2 favorites]

"but it's awkward at best"

I might be projecting here but I think you are probably unconsciously blocking yourself to some extent.

Deep personal conversation can be potentially exposing and embarrassing even though you consciously desire it. So the natural instinct is to keep yourself safe. The usual way to do this is to talk about something else. I mean if you are already talking about what his siblings do for a job you can easily end up talking about his childhood. Which is pretty deep. Unless you change subject and ask him about his favourite bar.

So the solution is generally:
- Notice if you feel anxious about the conversation subject or worried about exposing yourself.
- Focus more on what is being talked about here and now and stick with the subject.
- What Bardolph said.
posted by Erberus at 11:31 AM on January 4, 2015

Maybe this sounds trite, but I like to talk about wishes, hopes and dreams in the early stages of dating. What are your plans for the future? Life goals? Highest aspirations? What is most important to you? Another conversation tactic is to tackle the past -- although this depends on your comfort zone. Would you want to know about their dating history? Are you willing to talk about yours? Otherwise, you can ask a ton about their family, where they grew up, school experiences, and so on. You may also ask questions about why they made certain decisions - why did they get into their current career? Why did they pursue certain degrees or training (if they did)? What interested them in XYZ?

If you want to talk about philosophy and the human condition - you might just be up front and say that these kinds of things are really interesting and important to you. Bring up questions o topics you find fascinating and ask him what he think. Want to know how his brain works? Ask what he reads - and ask questions about what he says. Really listen to him. See how you react to his answers.

One thing you can also do is approach this initial, awkward, getting-to-know you phase as a game. Over wine, play 20 questions -- each of you asks a Q. Be spontaneous, see what happens.
posted by Gray Skies at 12:22 PM on January 4, 2015 [1 favorite]

Stop talking, start doing. Just sitting around can make most anyone boring.
posted by SemiSalt at 5:22 PM on January 4, 2015

Hiking, most people can't stop talking on a hike.
posted by notned at 5:53 PM on January 4, 2015

Unlike some posters above, I'd actually recommend against asking big open questions like "What are your passions?" If anything seems pressurey and job interviewey, don't do it. I'm a chronic oversharer, but even I get stumped by questions like that. Clearly I have passions, but it just seems so pretentious and awkward for me to have to list them out explicitly and I don't consciously think of these things as my passions, they're just things I do and think about.

Everyone has a different conversation style, but my tactic is usually me sharing a funny anecdote (pretty easy, because strange things happen to me all the time), gauge their reaction, and ask them a question if they've had similar experiences or whatever if they didn't ask me more prodding questions. I tend to overshare so people would feel more comfortable with sharing more personal information about themselves in the name of information symmetry. So in a way, it starts with you.

Where do my anecdotes come from? Sometimes something in the room reminds me something that happened to me, or there's something that's been on my mind lately, or my mood has been effected by X bizarre event. Eventually as I repeat the same anecdote over and over again to different people, I figure out what's a better way to deliver the story, kind of like a joke, and which parts people seemed kinda bored in or which parts people opened up more in. This sort of thing takes time, but it makes a lot of social interactions easier because certain stories are guaranteed proven icebreakers. It's not artificial though, as I genuinely enjoy telling these stories because they are hilarious and I personally laugh at the memories while thinking about them as I go about my daily life. The anecdotes-as-icebreakers thing doesn't always work, but it works often enough that I just keep at it anyway. I'm still working on being able to read people part and when to stop the oversharing, but enh, one thing at a time.

But yes, share things about yourself. Share funny stories, share sad stories, share angry stories, and share weird observations. Even vulnerable things or the issues that cause your heart to race. If you can be vulnerable, it's easier for other people to be vulnerable around you.
posted by Hawk V at 2:49 AM on January 5, 2015 [5 favorites]

nthing doing some active. Go for a walk, play a game... Being active helps use up some of the nervous energy, and makes it easier to talk.
posted by troytroy at 4:01 AM on January 5, 2015

Try the approach mentioned in this NYT article. The questions are listed here.
posted by marsha56 at 4:07 PM on January 13, 2015

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