Seven Tips for Making Good Conversation with a Stranger.

Every Wednesday is Tip Day.
This Wednesday: 7 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?”
“Really. I live on the upper east side.”
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.

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  • Cindy S.

    These are pretty awesome ideas. I’m going to a wedding tomorrow in which I probably won’t know the guests very well. Hope all goes well and you continue doing your informative and amazing tips.

  • jay yung

    you can start a conversation with an open qusetion like who,when,what,whereetc

  • theirmnd


  • therufs

    I’m amazed that you’d use a line like “Now, Paul, surely we can do better than that!” but not “We’re really working hard, aren’t we?” I think that’s pretty sassy!

  • Kamasutra condom

    Thanks for sharing lots of information. Its very useful to me.

  • some goose

    I think most people do this already, this was barely helpful :c sorry

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  • Debra Dylan

    Never ask if the person has children. If the person does, you are bound to hear about. Don’t laugh at something that’s not funny. If I make the unfunny comment, I usually say, “They can’t all be funny.”

  • CyberSylph

    I find that many people (especially men) love to give advice, so say something like “I’m thinking of getting a new car/computer/cellphone/game system/whatever, but I don’t know much about them. What features do you think I should look for?” or “Are there any interesting small museums or galleries nearby that I could visit tomorrow?” or anything fairly neutral that he can show off his knowledge about. Then thank him for all his help and he will feel like a hero (and maybe offer to accompany you to the computer store, museum, his favorite Thai restaurant or whatever). Also, I sometimes bring a prop so that people have something to ask me about. For example, I might carry around my sketchbook and draw something in it, or carry my purse that’s covered in pictures of characters from vintage cartoons, because everyone has at least one that they remember fondly from childhood Saturday mornings. I’m really shy, so I find that planning something to say and/or do ahead of time helps.

  • Augleigh

    I find that in many social situations people don’t want conversation, they want banter. Banter is something I am not good at. It’s being able to make the joke, the bon mot, the pun, the flirtation, to be fun, fun, fun all the time. Would be great if there was some advice on that.