Make Small Talk Suck Less: 10 Ways to Become a Conversation Badass

Adorable cat by Kelsey Beyer

Adorable cat by Kelsey Beyer

We’ve all been victims of awkward small talk. The guy who won’t stop talking about his labradoodle. The gal who answers every conversation question with a one word reply. The cheese platter you refuse to leave because it’s more engaging than your party companions.

Many of us even actively AVOID talking to new people because we’re afraid that …

The conversation will feel stilted.

We don’t know what to say in the first place.

Or, because we don’t know how to handle silences.

If that sounds familiar, you’re not alone. It’s easy to get choked up by fear and doubt when it comes to talking to people we don’t know. Especially if they’re attractive. Or a cheese platter.

While there’s no catch-all formula for excelling at the art of conversation (witty retort x genuine compliment / a chuckle + polite thigh graze squared = MASTERY), there are certain guidelines that can help you make conversations not only easier but ENJOYABLE, and make you feel like you’re building a real connection with someone, as opposed to stuttering or literally running away.

Here are 10 tips to take the anxiety and uncertainty out of conversations with new people.

1. Listen Well

As Stephen R. Covey said in his book The 7 Habits of Highly Effective People, “Most people do not listen with the intent to understand; they listen with the intent to reply.”

This is especially true if we are feeling nervous and want the other person to like us. But when we fail to listen well, that is, when we are paying more attention to what we’ll say next rather than what the other person is saying now, then the conversation is pretty much doomed.

Listening well also helps ensure that the conversation keeps its flow by providing you with information, “hook points” (more on that below), and other fodder to relate and respond to.

2. Ask Better Questions

There’s nothing inherently wrong with a “What do you do?” or “Where are you from?” type of question. Indeed, it’s part of the dance of getting to know someone. We can’t eradicate all boring questions from our lives. What we can do, however, is quickly move beyond them to get to more interesting topics.

So if you asked someone what they do and they replied, “I’m a nurse,” there are many different directions you could take it. You could ask about their aspirations:

“Have you always wanted to be a nurse or was there something or someone that tipped you in that direction?”

Or try to lead them into a story: “What’s the craziest/sweetest/grossest thing that’s happened to you on the job?”

Or relate it to your own life: “I have a lot of nurses in my family. Does it run in yours?”

Or ask something silly: “What kind of scrubs do you wear? I’ve always wanted the ones with dancing hot dogs on them.”

The important thing to remember is to try to ask leading questions (those that don’t have easy yes/no answers) and to show genuine curiosity. If you can get someone to think about their answers to your questions, it’ll make them feel more engaged and interested.

3. Have Better Answers to Common Questions

Since we can’t avoid every mundane question, it would behoove us to think about some interesting answers to said questions. Let’s take the gold standard, “So what do you do?”

If answering for myself, I could say, “writer,” but that wouldn’t be terribly interesting or give someone much to go on. Instead, I might say something like, “I exploit my life stories for money” (personal essayist) or “I help people have better sex and relationships” (advice columnist) or even bring up something I’m currently working on, “I’m writing erotic fanfiction based on The Bachelorette.”

Any one of those answers is easier to reply to than a mere job title because it adds intrigue and gives people fodder for their own questions in response.

If you have a “boring” job, you can do one of two things. You can either get creative with it or you can bypass it entirely.

Getting creative means thinking about what is most interesting about your job and spinning it that way. So “I’m a software engineer” becomes “I’m helping to design the next Candy Crush game.”

“I’m a financial planner” becomes “I tell people what they can spend their money on. NO LATTES FOR YOU.”

Or, if you’d rather skip job talk entirely, you can briefly mention what you do, but add what you actually enjoy or are passionate about in your life. For instance:

“Being a waitress is what pays my bills, but what I really love doing is volunteering at a bike co-op and brewing my own kombucha.”

The next time you’re faced with a barrage of boring questions, write them down and devise ways to answer them in a more interesting or unusual way.

4. Hook It Up

Hook points are any words the other person says that you can grab onto for further discussion.

So, to use a prior example, if someone said, “I’m writing erotic fanfiction based on The Bachelorette,” the hooks could be:

Erotica/sexy writing


The Bachelorette

Trashy TV in general

Any of these hook points could help fuel the conversation. Is it hard to write erotica? How many different ways can you say “vagina”? What’d you think of Fifty Shades of Grey? What is fanfiction exactly? The Bachelorette! I love that show. Who did you want to win last season? Or, I’m more of a Desperate Housewives kind of girl, m’self. What other reality TV do you watch?

And so on.

Harking back to our flirtation primer, you could flirtify these hook points by…

Teasing: “Erotica, huh? That sounds like a truly terrible job. Are you hiring?”

Statement: “That sounds amazing. I hope Chris Harrison make a cameo in a sex swing.”

Banter: “So when are you gonna write something about me?”

Playful challenge: “You like that show? I can’t talk to you anymore.”

5. Don’t worry about pauses

It’s natural for conversations to come to a stop. We are not sports announcers or the guy from the Micro Machines commercials (probably). If you find yourself in a situation where the talk has stopped, it’s ok! You don’t have to run away or start blabbering. Take a breath, take a sip of your drink, and move on to another topic. Make a small remark on something she’s wearing, the music that’s playing, etcetera.

Or, if you’d really rather leave, you can say something like, “Well, thanks for the chat. It was nice meeting you.” And make your exit.

6. Look them in the eye

Don’t be darting all around, watching passersby, looking at the floor, or checking your damn phone. Look at her when she’s speaking, because if you don’t, you’ll be perceived as rude or that you don’t care what she’s saying.

Plus, eye contact has all those other perks we talked about in the Confidence 101 primer.

7. Compliment genuinely

Compliments are a great way to show interest, connect, and make your conversation partner feel awesome. The rub is that they have to be genuine. Physical comments can be iffy, but fine as long as you don’t go overboard. Think: “You look great in that indigenous jumpsuit. I dig your style.” As opposed to: “DAT ASS, YO!”

A genuine compliment tends to be about who they ARE. For instance:

“Wow, you’re so career-driven. When I was your age, I wish I’d had your ambition.”

“You’re really well-traveled. It’s so cool how many places, languages, and cultures you’ve experienced.”

8. Don’t be a Debbie Downer

Try not to complain about how the world is going to shit. I know it’s easy to get sucked down that wormhole, but we are drawn to positivity in people, not those who remind us how awful everything is. See the good in people and in things and it’ll come back to you ten-fold.

Example: I was complaining to a friend about how a reading I was doing was on a Monday night. “Nobody goes out on Mondays,” I said.

She didn’t miss a beat: “That’s great! You’ve cornered the Monday night market!”

9. Be a storyteller

We all love a good yarn, and telling stories doesn’t have to be difficult or drawn out endeavor. Think of one or two stories you have told many times before (or that other people ask you to tell) and try to work them into your next conversation with a new person.

If they are embarrassing or slightly vulnerable, all the better! As Brene Brown reminds us, “We cultivate love when we allow our most vulnerable and powerful selves to be deeply seen and known, and when we honor the spiritual connection that grows from that offering with trust, respect, kindness and affection.”

I like to tell the tale of how a guy once tried to command me to orgasm by shouting “GET THERE!” repeatedly.

It never fails to get laughs (and questions about my life choices).

10. Stay open and curious

Approach all conversations with openness, warmth, and curiosity. You never know when you’re going to really hit it off with someone, and staying open to the possibility that your life will be transformed ANY MINUTE NOW is a useful (if weird) strategy.

Don’t put any pressure on yourself or on the talk itself. Instead, view talks with new people the way you would approach a wild kangaroo.

What will happen? Will it kick me in the face or will we bond and I’ll get to ride in its pouch?

Aaaaaand, don’t forget to practice. Real world experience, not reading blog posts (much to my chagrin!), are what we need to become masters of mouth flappery.

What say you? What has helped you walk the walk and rock the talk?

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