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?”
“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

[Vi]

Great post! I particularly liked 3,4 & 5. The tip given in #7 is new to me... I'm not sure I'd have the gall to try it out either.

[Positively Present]

Wonderful tips here. I love Wednesday Tip Day! :) One of the things I'm really working on right now is trying to be more friendly and social so this list was perfect for me. Thanks!

[Genevieve]

"“What are you working on these days?"

Of course, when you ask that, be careful who you ask (or rather, how you respond when asked, to be fairer!)- a non-law student friend of mine asked another friend of mine and I this recently. Baaaad (inadvertently so though) timing- we were in the middle of writing research papers and naturally thought that when this non-law student said, "So, I don't know much about XZY, what's going on with that?" he actually meant it. Let's just say he got way more information about international humanitarian law than he required!

[Nedra R.]

This is great, no matter if you are networking or just saying hey to folks at a party, thanks for sharing!

[Alex @ Happiness in this World]

When I asked myself why I found these to be such really great tips I decided it was because they all drive us to focus on the depths of the person we're talking to rather than on the surface. Depths in general are far more interesting, thus leading to more interesting conversation and maybe even real connections. Thanks!

[karen]

I think some of the follow-up questions might be a little too personal for someone you don't know well. I rely on asking people for advice based on their interests (i.e. ask a foodie about their hands-down favorite restaurant) because almost everyone loves to give advice. Another (more manipulative) way to keep a conversation going if you have met someone before, but don't remember a lot about them is to make inoffensive assumptions that you know are probably wrong. Most people have a natural inclination to correct you. "You're from Vermont, right?" "No, Rhode Island." "Oh that's right, I'm sorry. What brings you to New York."

[Jason D Barr]

My biggest problem has always been asking open-ended questions, due to the fact that I feel as though I may begin to pry into areas where I'm not welcome. I'd certainly rather not turn the mood even more uncomfortable in this situation! I think one way to set a positive tone is your tip #6. Much like the golden rule, you should react the way you'd like to be reacted to. Being a good conversationalist is mostly about making the other person feel special, I think.

At the risk of looking like I'm only here to share a link, I wrote a post about this very topic. It may be helpful to some folks who are looking for a framework to "cheat" in conversations. It's always worked well for me. Cheers! http://www.startbeingyourbest.com/2009/04/08/developing-people-skills/

[Gretchen Rubin]

It's interesting -- I often worry about prying or asking questions that are too personal. My husband, however, boldly goes into deep waters, and I've learned a lot from watching him in conversation. Usually -- though not always -- people seem gratified to see that he wants to have a meaningful conversation, and are more open to being forthcoming than you might expect. I think a lot depends on your demeanor -- he is able to convey respect and interest that helps people not to take offense. But I myself am very worried about overstepping boundaries, I understand that concern...

[sd]

great article. im 24 and still learning the art of conversation, i'm starting university in september and this will be a big help in getting to know people!

[Cheryl Schwartz aka aeropolowoman]

There are several people whose names my brain just won't remember. OK, I'll make a more positive statement -- I'm positive my brain won't remember their names. I've used all of the typical tricks to link face and name without apparent success, so with these tough cases I'll just call them by an obviously wrong name -- "Harry" -- and they'll quickly correct me -- "It's Alice."

[Sam]

Good stuff. Thanks very much. You're right though. #7 would take guts!

[Jon P]

Jeez, Gretchen. It's killing me thinking that some schmuck had the opportunity to sit next to you at a dinner and couldn't find something interesting to say, or find something interesting about what you do. Really! What could possibly be more interesting than the pursuit of happiness in all of its manifestations (art, politics, mysticism, the pursuit of love, looking for meaning)?!@#$*!!?

Here's an interesting conversation starter you failed to mention, but have already mastered: Do something interesting with your life. Then wherever you go, you'll have interesting things to talk about.

Just the same, thanks for the pointers for those of us who haven't been quite as brave with our occupational choices.

[Allen Shadow]

Good tips. Socialization often takes work.

[jkh]

meh

[communicatrix]

Omigod. You were totally fake-laughing at my bad jokes in Austin, weren't you!?

Haha. Kidding. (I hope.) I love the way you're basically saying to roll with it: to make a game out of things. I like to pretend I'm a journalist writing a story, or set up a challenge for myself where whoever gets the *other* person to talk the most, wins.

Damn, I'm competitive.

[Era]

I like the admit it solution to a laboured conversation. I believe that being honest and open are the way to go. Mind you, it's not the easiest, but in the end people appreciate not being patronized and not having to play games. At least I do. This is not a license to be rude, however.

[Era]

I like the "admit it" response to a labored conversation. I am at a point in my life where I want to just be me - honest me, without playing games or trying to fit into people's molds or perceptions of me. That has been making me happy. This kind of honesty is not the easiest path always,but I feel people appreciate not having to play games and not being patronized. However, this is not an invitation to be rude or hurtful.

[pbhj]

"So, how come you're so ugly ..."

[chica]

I love this list. Some great ideas for questions I wouldn't have thought of.

I don't think questions are always the best way of getting to know someone, though. You can often get a good response by sharing your own stories and experiences (without being asked). This can encourage the other person to do the same, and give them more about yourself that they can relate to. This seems less formal or intrusive to me than what I've come to think of as "interview style" questions (even though I think your suggestions are a lot more helpful than the questions most people ask).

Some people will just go into "receptive mode" when you do this, though, and just listen to what you have to say without offering much in response. So different approaches work better wth different people (surprise!)

Great tips, anyway

[Laurie PK, See Jane Soar]

I like talking about "the elephant in the corner"! That is, I've often talked about the fact that we have nothing to talk about, how uncomfortable it is, how often it happens, how boring it is to talk about the weather, and so on.

If you're struggling for something to say, chances are your partner is, too....and you'll bond over that fact alone. :-)

[Meream]

Great tips. I usually do everything except for admitting that things are going awkward. Will try that next time.

[Charlie]

Terrific post Gretchen and great tips and comments from many above (Alex, Jason and Jon). I often know instantly how a conversation with a stranger or a loved one will progress based on visual cues and attitudes and admittedly I shut down when I sense disinterest, negativity or that I'm being talked at. As I get older I'm finding more and more that I find it is the people that don't take themselves too seriously and possess a keen sense of humor that I find most interesting. Perhaps, because it is a demonstration that they can overcome the adversity life throws at them yet still maintain a positive outlook.

[Beth]

I have often received interesting responses to the question: "If you had the opportunity to make a change in career, what would you really like to do?". I have found that a lot of people have something they would love to be doing and become quite animated talking about it. One diminutive woman told me she would open a clothing store which catered for short women - until then she had had to do her shopping in children's stores, and loved the idea of catering to others in her situation.

[Silvia Wilson]

I like to ask, "Do you live here, or are you visiting?" and "What do you like about living/visiting here?" Then we can compare our favorites. These questions can prompt some interactive storytelling. I love to hear people's stories. Recently, I discovered that a stranger I met in Asia is actually a distant cousin.

[J Lewis]

If I may offer a hint of my own to your Hint #4, "Do you have children?" can be a really bad thing to ask some people.

If they do, you'll know, in which case it won't be at all difficult to hold up your end of the conversation; but if they don't, it could lead to a less-than-pleasurable moment.

It's like wishing a woman you don't know a happy Mother's Day. You have no idea what her story is, and you might be placing her in an awkward position of needing to be polite with a total stranger on a painful subject. My mother-in-law, who lost two of her three children, avoided going to church or to the store or just about anywhere in public on Mother's Day just so she wouldn't have to endure such an exchange.

[Alex - Unleash Reality]

Great article.

getting good at making conversation with strangers is a great skill that can lead to all sort of unexpected benefits... and provide untold happiness!!

i really like number 3 - not something you see again so it's refreshing to read something that isn't just rehashed from conventional wisdom.

i find it easiest to connect by connecting to the humanity in them, in their eyes and being with them fully without wanting something. pure offering value.

stumbled!
alex - unleash reality

[Bill]

I share the misgivings of some of the other commenters about the kid-related questions - for me, that's a sensitive subject. It's not something I'd want to talk to a stranger about.

In general, though, I like the idea of "boldly going into deep waters." It goes totally against the grain for me (I'm very shy anyway), but if it worked out, it would be *so* much better than bland, safe conversations about the weather, etc. One question I've thought of, but haven't had the guts to follow through with, is: What are your dreams for your life? If you could have the perfect life, how would it be different from the one you have now? I guess that could be a sensitive one too, but for people who are willing to answer, it seems like it could lead to a meaningful exchange.

I love the attitude that Ms. Communicatrix adopts: "I like to pretend I'm a journalist writing a story, or set up a challenge for myself where whoever gets the *other* person to talk the most, wins." That's fantastic.

Another thought-provoking post -- thanks!

[Joe]

I stumbled across your blog and rather like it. A couple of additions to making good conversation:

-A variant for number 3 is to ask "How do you like to spend your free time?" or "What to you like to do?". This focuses on what the person chooses to do, rather than what they may be forced to do (ie, work to earn money). Many people don't particularly like their jobs, and as you mention, the stock question party question is "What do you do?" which means "What do you do for work", and may mean "How much money do you earn" or "What is your status?"

-People like to speak about themselves, so, engage them about subjects they seem interested in...conversation is a dynamic process, not static.

Again, good post.

[kali]

I'm 39 weeks along in my pregnancy and am also about to become a parent for the first time. It would actually cause me a lot of distress if a person I had just met started asking me how I intend to do things differently in raising my child from what my parents did. My father left when I was 2, and my mother was emotionally and sometimes physically abusive toward me. These are the things I will do differently from my parents: not abandon, not abuse. The particular example conversation suggested in #4 around children is one I'd only hold with those who already know me and with whom I have a certain level of comfort. Even in that case, I would not be the one initiating it.

Other people without such negative parental baggage may have no problem answering these sorts of questions from acquaintances, but for those like me with parental abandonment/abuse in their past, it might be too hurtful to discuss with just anyone.

I like your other points, though, Gretchen. You've posted some ideas that I will keep in mind for future social occasions.

[Colleen Hannush]

I have a little game I play trying to place someone's accent. Be careful with Asian and Middle Eastern accents that could trigger cultural animosity, but even with locals, its nice to ask if they are born and raised in the area. It usually gives you enough to start working with and opens up other topics.

[Janet Barclay]

This is great advice, especially for introverts who find it difficult to initiate conversations and aren't generally interested in small talk!

[trs]

Nothing beats the way Monk does this on the TV show. He has "conversation cards" he uses because he so totally lacks conversational skills. Would be pretty awesome to break those out at a dinner party :-)

[J.S. Brooks]

Terrific ideas, especially when my social situations are increasing as I head for a new career in ministry. Now, what I really want to know is a little off topic, but still on socializing. How do you break into this sprawling blog community and start to feel at home? Is this similar to the party situation or is there something else that works here?

[Adam Levine]

The key to making good conversation with a stranger is to find something that both parties have in common. For example, a favorite sports team or movie. Topics to stay away from are things that most people are very opinionated on such as politics.

[Broderick]

You have no idea how helpful this is to me. I am a socialphobe and have a terrible time knowing what to say to someone cold. Thanks!

Having said that, oddly enough, suggestion #7 is easy for me, I have used it and it works. You either get a real conversation going by blowing the tension to bits, or you walk away from each other and stop wasting time and effort.

[kate]

Some good tips - especially #3 and especially now. When so many people are out of work, asking a broad question about what is keeping someone busy can help you avoid a truly awkward and painful topic if someone has just been laid off or is struggling through an extended period of unemployment.

[Mandy Cat]

Here's Tip No. 8, which would be provided by my husband if he were on this string instead of me. "Don't buttonhole perfect strangers in public places in order to give them unsolicited advice." He finds it embarrassing enough that I frequently strike up conversations with strangers in stores and restaurants. He particularly dislikes it when I tell the nice young couple at the garden center that they don't want that patio furniture set. They want one which doesn't require cushions so they don't have to worry about mildew and winter storage and which they may find at the XYZ Store on sale at 40% off in a few weeks.

I recently read "The Tipping Point" by Malcolm Gladwell. He described the various kinds of change agents among us. I fell into the "Maven" category, someone who thrives by accumulating and sharing useful information, by force if I have to.

So I guess here would be Tip No. 9, from me: Pish tush to Tip No. 8. And are you sure you really want that pre-cooked package of brown rice? You can buy at one-tenth the price in bulk at Sunflower Farmer's Market and freeze the leftovers.

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I have found that a lot of people have something they would love to be doing and become quite animated talking about it.

[ElizMcK]

I agree with a post above about some of these questions being too personal for a conversation with a stranger. I felt queasy and uncomfortable just envisioning someone asking me some of these probing questions, (which says a lot more about me than I'd like to admit).

I have an employee who constantly uses this technique to endear himself to me - he asks only personal questions - and it is really unnerving. I find it invasive to the personal boundaries I've set between myself and my staff. I'm not stodgy or impersonal, but I do feel there is a boundary that needs to be set in order to be taken seriously. This employee is a really nice person, but he is also a notorious gossip, which makes discussing personal matters even more uncomfortable. I certainly don't want to fuel his need for knowledge in this regard, as I've heard him relay some pretty inappropriate stories about others.

If I'm meeting a stranger, I will try to find out something that is within their area of interest or expertise and attempt to focus on allowing them to talk about it. Most people enjoy talking about themselves and love to share their passions. For example, if someone enjoys cooking, we can discuss restaurants, types of cuisine, cookbooks and authors, etc.

[sjhaughty]

It seems to me that questions like "how are you raising your children differently than you were raised?" could come off as invasive. And, several of these questions sound like interview questions, such as "what kind of magazines do you read?"

[tuula Kahilahti]

How many times have I wistfully wished that the wonder machine had been around in my youth.So many agonies that stretched on to adulthood would have been avoided.My ignorance of many things would not have been so glaring which of course led to the demise of my almost non-existing self esteem and unimaginable feelings of shame and inadequacy.Thank you Mr.Gates

[Kerri]

The question I hate getting is the "what do you do?" Not because of the initial question, but because of the follow-up "that must be so interesting." Not really. Unfortunately I have a job that is often portrayed on TV as being much more interesting that it is in real life. What a conversation ender. I don't want to lie, but these people seem to expect that I begin regaling them with interesting stories about my job. I never really know what to say.

[R. Hensley]

These were wonderful. I have a cousin that was in school for 10+ years and never graduated. We see each other once a year and frankly it is painful to try and visit with him. Other family members agree. "What's new?" and "How's school?" seemed to put him on the edge, perhaps even over the edge! I think I'll try your, “What’s keeping you busy these days?” From his FB posts he sounds like he does interesting things; but you'd never know it from his conversations!

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