Picture the following…

You’re at a party, you don’t know a single person other than the host, and they’re mincing about making sure everyone has drinks;

Or you’re at a family gathering, and the dinner table chatter is once again monopolized by the same incendiary politics or bitter arguments;

Or you’re with friends, and the conversation is stuck at surface level so you all turn up the music and pound the drinks harder;

Or you’re on a date and anxiously sweating over what to ask the person sitting across the table from you…

Awkward conversation with a date


As a team of (mostly) introverts, we’ve been in all of these situations. But even extroverts sometimes struggle to start conversations. This is exactly why we researched and wrote this guide: to put an end to awkward silences and cringe-worthy conversations… for good.

Hi! We’re Brainscape, and we feel your pain!

We’re the brains, minds, and hearts behind the world’s smartest study app, which we’ve put to use for an enormous spectrum of academic subjects and languages.

But we’ve also expanded our focus to the realm of personal growth, creating flashcard collections that are designed to improve your sense of humor (Funny Jokes), general knowledge (Get Smarter), emotional intelligence (Personal Development), and more.

And a really important part of personal growth is learning how to start conversations with strangers (and other humans)!

This guide will help you overcome this challenge with 7 key tips, while our collection of Conversation Starter flashcards will give you the perfect tools to sustain RICH conversations, lifting the curtain on the humans you’re interacting with, allowing you to know them better, learn from them, and really enjoy their company.

(Yes, this applies even to the people you’ve known for years.)

So, if you’ve ever felt awkward with people, struggled for conversation, or felt a little bored or uninspired with the people you spend time with, this guide—and the tools it recommends—is a game-changer for you!

Let’s get started…

How to start conversations with strangers, friends, and… anyone, really!

Awkward conversations with people

Tip # 1: Ask questions that inspire follow-up questions

The root of ALL conversations is the question.

Like a tennis pro’s swing, questions provide the force necessary for a conversation to take flight. So, if you want to start a conversation with somebody, all you have to do is to ask them a question!

Better still, ask them questions that inspire follow-up questions!

More conventional questions like “How are you?”, “How do you know Denise?” and “What do you do for a living?” may not achieve this noble goal… but what they DO do is establish whether someone wants to play tennis with you.

If they give you one-word answers, look bored, and don’t ask you anything in return, then you can assume that they aren’t interested. That, or they very simply have a lot on their mind. Either way, it’s time to move on.

Eye roll boring conversation

If, however, they ENGAGE, then it’s game on, and now you can pop open a fresh can of questions you’re genuinely curious to hear the answers to. For example:

Opening question: “What do you do for a living?”

Interesting follow-up: “What do you enjoy the most about your job?”

Another interesting follow-up: “If you could do anything in the world, money being no object, what would you do?”

Do you see how these questions could spark a whole lot of deep and meaningful conversations with someone you’ve only just met?

The cool thing is, you can try ‘em with anyone, and they’ll work, whether the person you’re speaking to picks up poop at a dog park or writes luxury hotel reviews for a living.

Some other interesting follow-up questions include:

  • What is the best advice you’ve received?
  • What’s the bravest thing you’ve ever done?
  • If you could be the best in the world at something, what would it be?
  • What is your guilty pleasure song?
  • Check out hundreds more right here…

These kinds of interesting questions reveal clues about the identity of the person you’re talking to and spark further questions. But more than any of that, they make the person you’re talking to feel like you’re interested in them and that makes them want to talk to you!

You’re totally welcome to pilfer the questions I used as examples in this guide but for hundreds more…

Tip # 2: Use Brainscape’s Conversation Starters to fuel your “chat”

Brainscape's Conversation Starters flashcards

As I mentioned before, there are many introverts—and some extroverted introverts—on the Brainscape team so we know how hard starting conversations can be. This is what compelled us to curate our Conversation Starter flashcards, which will transform your surface-level conversations into something much deeper, more thought-provoking, and even scandalous.

In these eight decks of 380+ flashcards, you’ll discover a glorious spectrum of intriguing questions from those that spark…

casual discussion, like “Do you have a secret talent?” and “What’s the strangest thing you’ve ever eaten?”

controversial debates, like “Which technology should not have been invented?” and “Should prisoners have the right to vote?”

… and the hilarious, embarrassing, and awesome secrets and stories we all harbor, like “Who in the room can swear in the most languages?” and “Never have I ever seen a ghost or UFO”, and so much more.

All you have to do is download the Brainscape app (Apple iStore | Google Play) to your phone, add “Conversation Starters” to your dashboard, and you’ll have 380+ prompts for conversation the next time you need a little social lubricant that won’t leave you with a hangover. (Keep reading for tips on how to use these flashcards.)

Oh, and for the parents out there, these questions are completely safe for young minds; although adult users can go wherever they like with the conversation prompts 😈.

Tip # 3: Overcome your knowledge insecurities

Nerds in conversation

One of the major reasons people feel too shy to start conversations with strangers—or get to know colleagues and acquaintances better—is because they feel insecure over how much they know about the world or other topics of the more… cerebral persuasion.

I’ve personally witnessed friends shrinking into the background whenever the conversation got “intellectual” or “worldly” because they grew up in an insulated, conservative family. Yet, I knew these people to be smart and interesting with stories that would make ‘Days Of Our Lives’ look like ‘Sesame Street.’

So, for starters, you are never NOT smart enough for any conversation. Everybody has a story to tell and interests that deserve to be shared.

But if you often find yourself around people who discuss world affairs, travel, history, art, literature, or whatever it is and you want to become a part of that conversation, there is a super helpful tool you can use to fast-track your learning curve… and it’s Brainscape’s suite of “Get Smarter” flashcards, which consist of the following three collections:

  • Knowledge Rehab: everything you wish you’d learned in school
  • Street Smarts: everything you wish you’d learned in life
  • Vocab Workout: the words you need to express yourself better

This is the ultimate collection of smart, digital flashcards that cover the baseline essentials of everything you should know about the world around you, from history’s greatest artists to the names of the common birds in your backyard; from the spices you should add to your foods to the capital cities of the world’s countries. And so much more.

Better still, they come pre-loaded FOR FREE with every Brainscape account. Yep, no catch. To learn more, check out this video...

So, if you tend to count yourself out of conversations that go deep on worldly issues, take my word for it: get you some knowledge rehab with our collection of Get Smarter flashcards.

Read: ‘How to sound smarter in conversations—and, actually BE smarter

Tip # 4: Remember that interested people are interesting

Curious, interested person

You don’t have to have a very interesting job or life in order to be an interesting person. It’s the thoughts you think, the books you read, the movies you watch, the hobbies you pursue, and the questions you ask that make you an interesting person.

In fact, the most interesting people I know aren’t interesting because they know a lot of things. They’re interesting because they’re naturally curious, ask perceptive questions, and busy themselves with finding answers, which makes them fun to talk to.

Interested people are interesting!

The other benefit of this mindset is that it compels you to ask questions about other people’s lives, which makes them feel special.

Never underestimate the importance of showing an interest.

Tip # 5: Mind your body language

Bad body language in conversation

You’ve probably heard it before: the majority of communication is non-verbal; a mixture of facial expressions, hand gestures, posture, and tone of voice. And if you haven’t heard it before, you’ve certainly FELT its impact on your own interactions, for example:

Has someone ever introduced themselves to you without smiling? Think carefully about your first impressions of them. You probably found them somewhat unapproachable, intimidating, unfriendly, or even rude.

What about someone who avoided eye contact while you were talking to them? You probably walked away feeling like you didn’t connect; that they weren’t interested in you or what you were saying.

Or what about trying to talk to someone who faces away from you and keeps fidgeting with their fingers or checking their watch? I’m sure you felt uncomfortable, rushed, and discouraged.

Do you see how important your body language is to conversations? In fact, it can be make or break! So, this is something you need to pay attention to:

  • Angle your body toward the person you’re talking to
  • Maintain eye contact
  • Be generous with your smile and laughter
  • Try not to cross your arms, fidget, or check your watch

Tip # 6: Practice makes perfect! Start conversations with strangers

Chatting to strangers on the train

You’re gonna hate me for suggesting this one, but it’s unavoidably true. The best way to improve having conversations with strangers is to just do it.

Here’s a little personal story…

I used to write for a lifestyle and leisure magazine in South Africa, which required me to attend fancy media events about twice a week with the who’s who of publishers and influencers. Before that, I’d worked from home as a freelance writer. In other words, my exposure to strangers was minimal. (Talk about being thrown in the deep end.)

This job forced me to mingle with complete strangers and at first, I found it overwhelmingly scary and utterly exhausting. But by the time I left that job, I was sashaying into those swanky events like I owned the place, greeting scores of people by name, and striking up fascinating conversations with people who were passionate about wine, food, and travel.

With time, I built up my resilience and with practice, my confidence. So this tip is about compelling yourself to talk to strangers*, which you can do by:

  • Approaching someone you’ve never met at a mutual friend’s party and getting to know them;
  • Complimenting a stranger on an item of clothing they’re wearing (or some other feature) while waiting in a queue or seated next to each other on public transport;
  • Asking a kind stranger for advice on where to eat or with directions; and
  • Telling a joke, if the right circumstance arises (see our next tip!)

Your conversation can be super short: a simple exchange. It doesn’t matter. The goal is to overcome the initial discomfort of engaging someone you don’t know. Do it enough times, and it’ll start feeling much more comfortable.

* Be mindful about how you approach strangers, please! Do it in public, with other people around, and definitely never accept any candy from them 😉

Tip # 7: Use humor!

Use humour in conversation

The most effective ice-breaker in existence is… a ship (a Project 22220 icebreaker called ‘Arktika’, if you must know).

The second most effective ice-breaker is… a well-timed joke! So, if you can master the art of good humor and memorize a repertoire of funny puns and one-liners, you’ll have a much easier time ingratiating yourself with new people!

This is where Brainscape’s ‘Funny Jokes’ flashcards and guide ‘How to be funny: 7 ways to improve your sense of humor’ come in!

Truth be told, there are probably 700 (or 7,000) tricks for improving your sense of humor, but the ones we discuss in our guide are the core skills for good humor: listening, collecting, and memorizing; being unexpected, relevant, and resilient; and of course, perfecting your delivery.

So give that a read and download our ‘Funny Jokes’ flashcards to efficiently build your repertoire so that the next time you meet new people, you’ll be primed and ready to let rip!

How to use Brainscape’s Conversation Starters flashcards

Before we conclude this guide on how to start conversations—and more interesting conversations at that—I wanted to give you a little run-down on how our Conversation Starters flashcards work.

Importantly, they’ve been designed as simple prompts, so you’ll be using them a little differently than if you were using Brainscape to study, learn, and remember information. Instead, you’ll be flipping through them in “Browse” mode.

To do that, tap into the specific deck that interests you (e.g. Deep Discussion Questions, Relationship Questions, How Was Your Day, etc.) and select “Browse” mode, which is right next to the big blue study button on mobile. If you’re using our web platform, you’ll see three little dots to the right of each deck. Tap on that and select “Browse’ mode.”

This will allow you to swipe through the flashcard questions without having to flip them over to reveal the answers (because we don’t provide those: your friends will) or having to rate your confidence level, as you would if you were actually using Brainscape to study.

Also, you should bookmark your favorite icebreakers in the mobile app ahead of your various shenanigans—parties, weekends away with friends, business offsites, etc.—so that they're lined up and ready to go when you need them!

Final thoughts on starting conversations

Friends having fun conversations

Brainscape is a team of humans who are more than a little acquainted with social awkwardness. This is why we put our heads together and curated a collection of Conversation Starters flashcards that you can take with you anywhere you go and use with anyone in any social situation to directly prompt conversation.

You can also use them on the sly when no one’s looking if you need a little help. And, of course, they’re HUGE FUN to flip through with a partner (on a date); a group of friends (at your next weekend away or hang-out); and colleagues (on a business trip, off-site, or retreat). Seriously, you may think you know them until you get them to answer some of these questions!

Then, armed with these flashcards and the advice in this guide, you will have everything you need and the newfound confidence to rise to the challenge of any conversation.

Also be sure to check out:

And these awesome resources: