how to make chit-chat

3 Things That Make Chit-Chat Oh So Awkward

How many times have you met someone, had a bit of small talk for 2 awkward minutes & moved on never to speak with that person again? Every person you ever meet isn’t going to be your friend but we do need to build new relationships actively. We’re social animals and need to have relationships with people.

We need to start conversations with people for professional reasons as well. This is how we get new jobs & gigs and get promotions.

Friends drop off. They get married and have kids. People move. We have to work to make new friends and maintain those relationships throughout our lives. But it’s not easy. We get new jobs where we have to meet & have good relationships with our new colleagues.


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Small Talk is Essential for Building Relationships

Starting conversations occurs when you’re meeting new people but also when you’re in the conference room & the meeting hasn’t started yet. Transition times I call them. Just before the job interview starts. (Crickets)

Before I started this piece I read every article I could find on the interweb about starting conversations.  People are still recommending that you ask questions (NO! Don’t do it!) and talk about the weather (Not. joking.)

So why the awkward conversations? What is it that you’re doing wrong that’s making your introductory conversations awkward? I’ll tell you.

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Don't ask questions. Don't.

Exactly the opposite of what everyone tells you, right?

Nobody wants to answer the questions “What do you do?” & “Where are you from?” Nobody does. So why do we keep asking? People have been asked that question countless times; they have routine answers that bore even them when they tell the stories.

Where people are from & what they do are details that are best left for after you get to know someone a bit. Unless you make your decisions about people based on that information. “Oh. You’re a plumber? Ba-bye!” Making conversation isn’t Tinder, folks. We don’t need the specs before we start to chat.

Very often after these questions are answered you’ve reached an awkward brick wall. The conversation goes nowhere and there’s an awkward silence. Here are 2 examples of awkward small talk. Have they ever happened to you?

Q. Whadja do this weekend?

A.  (Mind draws a blank) Uuuuuuhh. I did my laundry… nothin’ much

Q. Hey! What’s going on?

A.  Uuuuuhhh…nothing…things are good…how about you?

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Have you ever gotten into the Greeting Loop?

Hi! Nice to see you! How are you?

Great! Great! How are you?

Good & you? ad infinitum.

That’s awkward.

Reminds me of this movie clip: [Do you like… Cheese?]

Here’s the deal. I’m not saying don’t be interested in what others have to say. Our goal is to get people to talk. Counterintuitively, asking questions doesn’t help us achieve that goal when we don’t know someone well.  

When you’ve asked some boring questions, people begin to get nervous & they start thinking, “Oh, Jeez! What am I going to say next!” Many people think their stories of where they’re from & what they do are boring to others.

Solution 1.  Have an arsenal of anecdotes until you learn to create them on the spot.

Solution 2. This sounds scary, but it’s magic:  Talk about your emotions. The emoji of conversations.

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Arsenal of Anecdotes

I was supposed to meet friends at a Little West 12th Street restaurant. I had never heard of Little W12! This was before the days of GPS on your phone. I was actually afraid I wouldn’t find it! Isn’t that silly?!

What a crazy fear. I got there early, so I sat at the bar next to some guy & I told him that I’d never heard of this part of town & that I was actually afraid I wouldn’t find it. He was able to relate & told me his tales on the topics. By the time my friends got there, he & I were having a hoot & a holler.

Talking about how you feel about something makes people relate to you. It disarms them. Sharing emotions like fear and embarrassment warms people up and establishes strong ties at the onset, eliminating the need for boring Q&As.

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Small talk. Don't make it all about you.

If you really want to establish strong relationships, don’t reply to everything someone says with a story about you. We call those people one-uppers & they get tiresome really quick.

You:  Hi where are you from?

Stranger:  I’m from London.

You:  Oh. I’ve been to London. Do you know John Smith?

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Where are you from?

I travel down to Austin a few times a year to help a corporate client. It’s awesome. (Or as my 7 year old says, “Saucesome.”) Very hospitable folk. Always take me out after work to check out the amazing food & beverages. Margaritas! But I digress. 

I often stayed at the same hotel, and a girl that worked there asked me every single time where I was from. Every time I check-in, she goes, “Where are you from?” I’d tell her, “I live in Manhattan.” she’d say, “I hate New York. I went there once, and there was steam coming out of the ground; it was so dirty.” That was her version of small talk.

I’m sure she wasn’t trying to be my friend, mind you, but insulting where I’m from is not going to make me like you. This story contains both errors I’ve mentioned thus far. Asking, “Where are you from?” Then making where I’m from be about her.

Side-note: “Where are you from?” is a difficult question for most people to answer these days. Where am I from? I’m from a small town on the north shore of Long Island. I’ve lived in quite a few places since then. Most people ask these questions just because they’re making conversation. I think we need to work a little harder than that.

But certainly, practice the answer to that question so you can share something interesting that gets people talking.

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Compliment, don’t comment

If someone changes their hair color they’re usually cognizant of it. You don’t have to tell them. “You colored your hair.” Those are some shark senses right there. Just say, “Wow! Your hair looks great!” Or if you can’t bring yourself to lie, talk about something else. People know when your compliment is not genuine.

I just get off the plane in Honolulu, go straight to Duke’s in Waikiki for the first night of the family reunion & my cousin gives me a hug & says, “You smell like you just got out of a tanning salon.” That is a comment. I have no idea what it means, I’d like to think I smelled ok. Maybe he thinks the tanning salon smell is a good one, I don’t know. One thing’s for sure, not a great conversation starter.

One of my clients would go to work every day & the guy she sat next to would comment daily on what she was wearing. “You’re wearing a blazer, aren’t you hot?” “You’ve got a skirt on–got a date tonight?” Needless to say, he was never invited out for happy hour after work.

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This brief introduction will get you started on the road to speaking Standard American English.

Complimenting is Kind (& Makes Great Small Talk)

Compliment within the boundaries of appropriateness, of course. I personally don’t think it’s appropriate for a colleague to comment or compliment a woman’s skirt. To keep the conversation going after a compliment, you can ask a question. I know I said no questions, but make sure it’s a unique question, and as long as you have a cool reply to the answer it’s ok!

For example, I was at a snack bar & my bag was on the counter. A guy comes up to me, says “That’s a great bag! Where did you get it?” A great opening question that is also a compliment. After I told him, he said, “It’s my sister’s birthday I’m going to get it for her.” We chatted for a bit after that. After he got my digits he confessed it was a lie. His sister wasn’t having a birthday. 

Kudos to him! It takes courage to start a conversation with a total stranger, and his little white lie didn’t do any harm. His sauceome small talk resulted in a new great friendship!

Don’t let the truth get in the way of a good story–or conversation starter!

Ok, Your Turn to talk about your experiences with small talk!

Tell me what your amazing conversation starters are! Have you ever had any embarrassing or relationship sealing small talk moments?

Watch this awesome video of Ita Olsen: Why am I Not Automatically an Incredible Speaker


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8 thoughts on “3 Things That Make Chit-Chat Oh So Awkward”

  1. Really enjoyed this article Ita. It got me thinking. I like the point you make about avoiding stating the obvious. It adds nothing to conversation and can make people just feel awkward e.g. “You’ve had your hair cut.” “You’re wearing a skirt” Both of those would be a sure fire way to end a conversation with me immediately as I would either think the person is being a smart ass and mocking me in some way or otherwise assume they are just a bit stupid and have nothing to contribute other than literally saying aloud the things they are noticing as they are noticing them!!

    You’ve had your hair cut sounds so much better rephrased as, “wow that new colour looks great” or “your hair looks good. I like the new cut”.

    I think people feel awkward giving compliments and just letting them hang there in the air. They feel like they have to follow it up quickly with something else…which is when they fall into the trap of making it all about themselves or asking loads of needless questions.

    1. Thank you, Mary! And you bring up some thought-provoking points. Feeling like you’re being mocked is very common. We all feel that way sometimes when usually it’s not the case.
      Thanks for the comment! You’re at the top of the commenters at the moment 🙂

  2. i was always taught to ask questions! that’s the advice everyone has given me on first dates, any time i meet someone new, etc. Also, I hate people who just answer questions and don’t ask any back when you meet them. It is very telling of someone’s character if they are a question asker! (As long as they aren’t noisy questions)

  3. Compliment not comment – this totally worked for me in the past! I once complimented a friend’s keychain, and she spent a good ten minutes happily sharing where she got it and what it meant to her. Definitely a good camaraderie builder!

  4. I’m chuckling to myself thinking of how many times I get stuck in the “greeting loop” at work. I cringe every time it happens. I am definitely that person who doesn’t know where to take the conversation beyond that simple interaction. This is why I love tip of “compliment, don’t comment”. It seems like such a natural transition from a basic greeting to a flowing conversation.

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