Seven Tips For Making Good Conversation With A Stranger

I posted before about tips for knowing if you're boring someone and tips to avoid being a bore. But while it might be fairly easy to avoid topics that are likely to bore someone, it's much harder to figure out what to say if you want to be interesting. Making polite conversation can be tough.

"So where do you live?"
"Chelsea."
"Really. I live on the Upper East Side."
"Great..."
Painful silence.

Here are some strategies to try when your mind is a blank:

1. Comment on a topic common to both of you at the moment: the food, the room, the occasion, the weather. "How do you know our host?" "What brings you to this event?" But keep it on the positive side! Unless you can be hilariously funny, the first time you come in contact with a person isn't a good time to complain.

2. Comment on a topic of general interest. A friend scans Google News right before he goes anywhere where he needs to make small talk, so he can say, "Did you hear that Justice Souter is stepping down from the bench?" or whatever might be happening.

3. Ask open questions that can't be answered with a single word. "What's keeping you busy these days?" This is a good question if you're talking to a person who doesn't have an office job. It's also helpful because it allows people to choose their focus (work, volunteer, family, hobby) -- preferable to the inevitable question (well, inevitable at least in New York City): "What do you do?"

A variant: "What are you working on these days?" This is a useful dodge if you ought to know what the person does for a living, but can't remember.

4. If you do ask a question that can be answered in a single word, instead of just supplying your own information in response, ask a follow-up question. For example, if you ask, "Where are you from?" an interesting follow-up question might be, "What would your life be like if you still lived there?" If you ask, "Do you have children?" you might ask, "How are you a different kind of parent from your own parents?" or "Have you decided to do anything very differently from the way you were raised?"

5. Ask getting-to-know-you questions. "What newspapers and magazines do you subscribe to? What internet sites do you visit regularly?" These questions often reveal a hidden passion, which can make for great conversation.

6. React to what a person says in the spirit in which that that comment was offered. If he makes a joke, even if it's not very funny, try to laugh. If she offers some surprising information ("Did you know that one out of every seven books sold last year was written by Stephanie Meyer?") react with surprise. Recently, I've had a few conversations where the person I was talking to just never reacted to what I said. I was trying to be all insightful and interesting, and these two people reacted as though everything I said was completely obvious and dull. It was unsatisfying.

Now, what to do if a conversation is just not working, and there's no way to use the "Excuse me, I need to go get something to drink" line? Recently, at a dinner party, the guy sitting on my right side was clearly very bored by me. He explained to me at length about how happiness didn't really exist, but after setting me straight on that subject didn't want to talk about it anymore, and after a few failed attempts at other topics, after an awkward pause in the conversation (my fault as much as his), he said, "Um, so where are you from?" It was such a listless, uninspired effort that I leaned over, put my hand on his arm, and said meanly, "Now, Paul, surely we can do better than that!" and changed the conversation. (It is moments like that that make me happy that I basically gave up drinking.)

So what can you do when the conversation is such a struggle?

7. A friend argues that you should admit it! "We're really working hard, aren't we?" or "It's frustrating -- I'm sure we have interests in common, but we're having a difficult time finding them." Clearly this is a desperate measure, but my friend insists that it works. I've never had the gumption to try it, I have to admit.

What are some other strategies for starting an interesting conversation with a stranger? What have I overlooked? On a related note, here are some tips if you can't remember someone's name.

* I'm a huge fan of Twitter, in part because it has helped me find so many great writers and great information, and one person -- and blog -- that I discovered on Twitter is Gwen Bell. She writes about branding, social media, and creativity, and always has fresh, interesting things to say.

I send out short monthly newsletters that highlight the best of the previous month's posts to about 20,000 subscribers. If you'd like to sign up, click here or email me at grubin, then the "at" sign, then gretchenrubin dot com. (sorry about that weird format -- trying to to thwart spammers.) Just write "newsletter" in the subject line. It's free.

Comments

[MerrieWay]

In the day of cyber friends (so-called) it's shell-shock for some of us to speak with more than a sound-bite or trite gibberish. Assuming the stranger isn't a potential stalker or strangler, a big smile is always a staple ice-breaker. Music in the background helps with the jitters, if there's an attraction bubbling up from inside.
If it's a business gathering requiring protocol and expected social dribble...MerrieWay becomes a good listener and often a repartee naturally starts up and adds to life's adventure.

[Mercedes Beene]

Jeez...what's the BFD about making conversation? The fine art of small talk seems to elude most folks. It's rather simple: it's all about the other person, not you. Use the word "you" more times than you do the word "I."

As an opening line, offer a simple and sincere compliment., without being obsequious. Most people react well to being complimented. Yesterday, for instance, I had a fabulous lunch at a new restaurant. Saw the manager later in the day at the parking lot . I approached him (a perfect stranger) and complimented him on the chef.

Before you know it, I found out that this fellow was originally from Brooklyn, NY, like myself (we both live in Texas, now) and we had a delightful 5-minute conversation that left us both feeling great. I learned a lot about his future plans for the restaurant and other interesting tidbits. He met a satisfied customer.

And, that was that. No hidden agendas, no intrusive personal questions. Just a small bit of small talk.
My husband always tells me that "I have never met a stranger." Perhaps. It does help to be endlessly curious, I suppose.

[wideawakenow]

Some of these questions sound more like a job interview or something therapist would ask you, not a stranger at an event.

[gallon]

How about this at a job interview:
"What newspapers and magazines do you subscribe to?"

answer:
"All of them"

I've heard that is a good line.

[Archivist1000]

Oh I laughed at # 5 !!!!!!!

Forever to be known as the GOTCHA! question ............ yes, we DO learn so much about a person, depending on their answer!

LMAO

[Goliadkin]

Yeah, especially when the answer is "all of 'em"!

[noaxe397]

I like #7. But I think I would have a problem bringing up some of these conversation starters with a stranger the first time at some event (what magazines do you read? How is your parenting different from your parents?) Many women, I believe would find an ick factor here. I've found these types of questions are picked up by women as desperation probing.

[LLisaLL]

I'm a Number 6. I get stuck with people telling me the not-so-funny joke or the boring story and I do my best to react positively. The problem is, I must do it pretty well because they're encouraged to go on, and on, and on until I have to gracefully flee or be rescued.

[richdibo]

A joke about the setting often breaks the ice. Like at the gym: "I see you come here often, working out losing weight. You're looking good. Remember that you're suppose to call me when you reach 145 pounds."

[richdibo]

Never tell a fat person, "from a distance it looks like you were sitting on a bean-bag chair."

Now that would be a conversation stopper.l

[richdibo]

Ask getting-to-know-you questions. "What newspapers and magazines do you subscribe to?

Suggestion #5 would not work very well with Sarah Palin.

[hidflect]

No.7 is my secret pick-up strategy. Take the point of view from outside the two of you. e.g. "Hi, you'd better watch out in case some strange guy comes up and start talking to you.. oh.. " Comedians do this all the time. It variously known as the "man from Mars" approach.

[richdibo]

I sometimes have success with boasting my prodigious sexual technique.

[Goliadkin]

That's called "trolling for freaks."

[Badbone]

Yeah but at some point they'll find out you've been lying to them. Then what?

[JBL55]

Asking "Do you have children?" can be a really bad idea.

If the person has kids, you'll find out soon enough, if you haven't already. Most parents can't not talk about their kids. But if one or more of those children are no longer living (as was the case with my mother-in-law), it can make for a less-than-­pleasurabl­e moment.

if the person does not, "No" is one of those short answers that can fall with a thud. Many people who don't have children aren't happy about it, making for another kind of less-than-­pleasurabl­e moment.

Yep, asking a personal question of someone you've just met can really backfire. Stick to the weather, baseball, gardening, books, whatever.

[VoteOnPaper]

Well done. Thank you. It goes something like this...

"Do you have kids?"

"No."

"Really? I'm surprised. You're so great at making them laugh and keeping them interested.
You should consider it."

*sigh*

[barriosbabe]

I was in a graduate school interview for summer employment and I asked one of two stuffy suited guys "what projects are you working on right now?" The guy got very mad, yelled, said "I'm an attorney, I don't do project work!"

===

How do you know our hosts, and What's keeping you busy these days, are pretty good.

[doug108]

Good God.

[VoteOnPaper]

Lawyers don't work on projects?

[Stargazingchick]

Why is this rarely ever an issue in Europe? Ah, I remember, because people are less guarded and you don't have to sift through meaningless phrases that don't get you anywhere.

[barriosbabe]

Thank you for posting that! I recently had to work in Italy. I had forgotten how easy conversation with strangers is there. I've been musing about why. I think, for me, it struck me that people there are generally more probative, more curious, less inhibited, -- and perhaps most of all very well informed. Let me give you one of many examples. We stumbled one night into an empty cafe bar in Parma; within about one minute the father daughter owner team was sitting down with us and having a super lively convo regarding lifestyles, politics, you name it! How likely is that in the U.S.? with total total strangers in public? The other thing therefore is that they are less suspicious?

[krisgarfield]

Very true. I was raised by a European mother, and thankfully, learned not to be fearful and unnatural. I'll talk to anyone (ok...maybe not a flasher) and I'd say about 50% of the time, I get a positive response. The other half...well...let's just say I live In Los Angeles where many folks dont have "sunny" dispositions. I think that's why I tend to hang out with people who may be either be Americanized Europeans or Europeanized Americans. I'm of the former category, and feel blessed. When in Europe (well...when it was affordable) I was so relaxed. Never felt lonely.

I think many Angelinos could benefit from this and become happier. It is difficult due to our total dependence on cars...hopefully we'll catch up with most cities and finally have a mass transit system where people will actually TALK to each other.

[CAPTAINSKIPPY]

Yes, Americans are too fretfully busy, and worried about keeping up with Mr&Ms Jones. Our family always enjoys being abroad, especially during vacations.

[Natalee]

Are you kidding?

[deepintheheartoftejas]

Yes, find a topic everyone can agree on: Bush screwed up everything. Democrats will bemoan the destruction of the strongest economy of the past century, Republicans will gripe about the now-permanent loss of their only Congressional majority since 1929, Libertarians will weep about the loss of civil liberties... and if they try to argue that Bush wasn't bad, you know you're talking to someone utterly insane, and you should probably back away very steadily, using quiet tones so as not to upset them.

[GayleAlstrom]

When I first came to NYC, when meeting people I would ask them where they lived, just trying to start a conversation, and they would look at me suspiciously as though I were getting too personal and only jwanted the information for nefarious reasons. I think what questions one asks depends on what city you live in.