How to Start a Conversation (+55 Examples You Can Steal)

Look, we’ve all been there...

You see someone...and you wonder how to start a conversation with them. 

Then you feel it…

Your mind starts to race - maybe so fast that it starts to go blank. 

“What should I say?” “No, that’s stupid, no one says that!“

And by the time you psyche yourself up to start the conversation, the other person has ordered their tall Americano and sailed out the door.

Ah, such is life, you tell yourself. But it doesn’t have to be this way! 

With the right gameplan, you could be chatting up tall Americano right now and making a new friend.

I know...easier said than done.

​Learning how to start a conversation and developing a gameplan to help you practice and grow your newfound skills takes effort, know-how, and guidance. 

Luckily, you’re in the right place.

Simple Beats Complex!

When my clients ask me how to start a conversation, my first response is this:

While what you say first IS important, it’s not as important as what you say second.

In fact, for most of my clients, the best conversation starter is: “Hi, I’m [Your Name].”

I know, I know...

It feels almost too simple. But it’s often how we follow up that first statement that makes or breaks the interaction.

In this article, you’ll learn:

• Simple conversation starters for nearly every occasion
• How to start a conversation over text or DM
• How to be approachable
• How to keep the conversation going once you start it
• How to make starting conversations automatic

Quick Conversation Starters:

If you’re nervous or feel awkward about putting yourself out there, it can help to have a few good conversation starters in your back pocket. 

I’ve divided these up by situation to make it easier to browse. Look them over and choose the ones that work for you. 

Remember - it’s all about being approachable and genuine!

Don’t put too much pressure on these first few moments. It’s less about what you say than about how you say it. 

How to Start a Conversation at Work

via GIPHY

Work functions can be a special kind of hell for some of my private coaching clients. 

It’s all the social pressure of being at a party - but it’s mandatory.

And supervised.

And you’ll be seeing these people every day afterward.

Don't worry!

All of these conversation starters are light, work-appropriate, and should get a meaningful conversation started when you follow them up with interested questions:

• What department do you work in?
• How long have you worked for the company?
• Hey, I don’t think we’ve met, I’m [Your Name]. 
• Been working on any interesting projects recently?
• What’s your favorite part of your job?
• Did you relocate for this job or are you from around here?

How to Start a Conversation at a Party

via GIPHY

Parties are supposed to be fun! (Who knew?!)

But for many of my clients, parties bring social hesitation and fear.

​Talking to strangers - or even friends you haven’t seen in a while - can sometimes feel overwhelming and impossible. 

But with these conversation starters up your sleeve, you’ll be the life of the party! Or at least the life of your corner of the party. 

• How do you know the host?
• How did you wind up here?
• Are you from [current city you’re both in]
• I love your [shirt/hat/watch/shoes].
• Hey, I’m [Your Name]. 
• What do you do for fun?
• What’s the last movie you saw?
• What’s the last thing you read?
• Have you been on any interesting trips recently?

How to Start a Conversation at a Meetup or Class

Meetups and classes have the benefit of being structured.

Everyone signed up to be there and came specifically to gather and learn or do something together. 

This takes a lot of the pressure off you because you know the people around you signed up for this!

​Try some of these conversation starters to pique interest and make new friends:

• Hey, it’s my first time here, is this the [Meetup Name] Meetup?
• Hi, I’ve never tried a [Class Name] Class before. You?
• Hey, I’m new here. I’m [Your Name]. 
• Hey, is this your first class? I’m [Your Name].
• I’m so excited about [class subject]! What got you interested?

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How to Start a Conversation with Friends

Even once you’ve become friends with someone, you may find that you’re struggling with how to start a conversation. 

Maybe it’s been a while since you’ve talked, or maybe you have different things going on in your life now… Whatever it is, don’t worry. You’re not alone. 

All relationships take effort and it’s completely normal for there to be lulls in conversation. 

Try some of these conversation starters to shake it up:
​

• Hey, have you seen this [Link, video or meme]?
• Hey, haven’t reached out in a while, how’s [specific thing] going?
• I saw on Facebook that you [thing they mentioned]. How’s it going?
• What new hobby would you start if money and time were no object?
• Have you found any great new [music, books, movies, comics, games, etc.] lately?

How to Start a Conversation at a Dinner Party

Dinner parties are great! 

You should have at least one thing in common (the host). It’s also a low pressure environment because everyone there has been “vetted”, so there’s not that feeling of interacting with complete strangers.

• How do you know the host?
• I heard [Host] mention that you have/did [some specific thing]. That’s so cool!
• I overheard that you’ve [some specific thing]. That sounds so interesting!
• Have you tried the [dish, food, drink]? What did you think?
• What’s your favorite cuisine?
• Do you like to cook?
• Hi, I’m [Your Name]. Try the [dish, snack, drink] - it’s delicious!

Simple, All Purpose Conversation Starters

Often, the best conversation starters are the simplest ones. 
​

• “Hey, I’m [Your Name].”
• “Hi, I don’t think we’ve met before, I’m [Your Name].”
• “Hey there, my name’s [Your Name].”
• Hi, I’m [Your Name]. Nice to meet you…[Leave space for them to introduce themselves]
• Hey, I’m [Your Name.] Are you having a nice time?

Contextual Conversation Starters:

No matter where you are, it’s best to focus on contextual conversation starters. 

Conversation starters become waaay easier when you’re starting a conversation about the environment or situation that you’re both currently in.

This makes the conversation starter feel natural for both people and leads to a better conversational flow.

Example: Starting conversations in a coffee shop

• “I’m looking to switch things up, what’s your favorite thing here?”
• “That order sounds awesome, is it your usual?”
• “I’ve never been here before, do you have any good recommendations?”

Example: Starting conversations at work

• “Hey, how was your weekend?”
• “Hey, how’d that project go for you?”
• “Did you hear about [new policy, new hire, company outing]? What do you think?

Example: Starting conversations at a meetup

• “Hey, this is my first time here, I’m [Your Name].”
• “I picked this meetup because [your reason]. How about you?”
• “How long have you been interested in [meetup subject]?”

See how much more natural that feels? 

An easy way to start conversations without memorizing a bunch of icebreakers is to become an observer of your surroundings. 

Take note of what’s going on around you, comment on it, and invite others to give you their opinion as well.

Boom! Conversation started!

The Anatomy of Starting a Conversation

As I’ve said before, it’s less about what you say than how you say it when you want to start a conversation. 

That may sound like a weird thing to say in an article about how to start a conversation, but the lists above are for your benefit. 

Having a list of possible conversation starters at your beck and call can make you feel more prepared and more confident.

And confidence is key to pretty much every successful social interaction.

At the risk of sounding like every movie of all time… The magic was in you all along, guys.

So use these steps alongside your chosen killer conversation starter and you’re one step closer to achieving your social goals!

Before speaking, you should be in the other person’s field of view. Simply put, there shouldn’t be ambiguity that you’re talking to them. 

Often, this can be accomplished by entering their field of view and making a little eye contact.

*Mask note: If you’re wearing a mask, “warm” eye contact is super important. Smile under your mask until the corners of your eyes start to crinkle. That primes you for warm eye contact.

The first thing you say doesn’t matter as much as the second thing. The first thing can literally be “Hi.”

The second thing can be something specific about the environment you’re both in.

• “It’s chilly in here!” 
• “I love this coffee shop - are you a regular here too?”
• “That sounds like a great order! I’ll have to try it sometime”

Once they’ve responded, gauge their reaction and take the conversation deeper with a question, or say “Have a great day!” and move on, taking the glow of a successful conversation started with you!

It REALLY can be that simple! 

Once we break down what can feel complex and intimidating, notice how simple starting a conversation can be!

​Say hi, gauge interest, ask questions or make statements, and move on!

Being Approachable is Key

Starting a conversation is just the beginning.

Once you find an entry point, your focus should be on being approachable. 

Giving off the vibe of “Hey this person seems positive and fun to be around” is how you keep the conversation going - and how you get a chance for a second conversation!

How to give off an approachable vibe:

• Open body language - uncrossed arms, turned toward the person, relaxed shoulders and facial muscles, weight shifted onto one hip. Open body language invites the other person to stay and puts them at ease.
• The slight smile - A smile that suggests that you are happy to be where you are. Just turn the corners of your mouth up. You don’t have to show your teeth the whole time! 
• Be socially bold - This means being proactive, starting conversations first, etc. Remember, most people are so caught up in their own thoughts and insecurities that they never think about starting a conversation themselves. Most people will be flattered that you spoke to them first, especially if your overall vibe is positive.

Fixing the fear of starting a conversation:
​Outcome (In)Dependence & The Spotlight Effect

Starting a conversation (especially with someone we don’t know) can be a scary proposition.

What if they think we’re stupid?

What if they think we’re weird??

You’re not the only one thinking that. 

In fact, most people at this party or work function or meetup are worried about the exact same thing! This is what’s known as the Spotlight Effect. 

The Spotlight Effect is a cognitive bias that lives in our minds and whispers things like, “That girl over there is laughing - she’s definitely laughing about your stupid t-shirt! Why did you pick this shirt?!”

In reality, that girl is laughing at her friend’s joke and wondering, “Is my laugh too loud? Oh my god, I sound like an idiot - quick think of something funny to say back!”

In a very real way, you are hallucinating when you fall victim to the Spotlight Effect. 

(Real talk: we ALL hallucinate from time to time. This is normal.)

But understanding this cognitive bias can be incredibly empowering! 

No one is judging you! They’re all too busy trying not to be judged themselves! 

That means that if you do goof up, it’s not nearly as big of a deal as your brain tells you. Everyone will forget what you said while they obsess over the stupid thing they said!

And that leads me to the next big cognitive bias that gets in the way of good conversations - Outcome Dependence. 

Outcome Dependence occurs when we get so wrapped up in a particular outcome that we want (or want to avoid) in a social situation, that we get blinders on. 

When you’re too focused on the outcome (not messing up, getting a number, etc.) you’re not fully present in the situation. 

People can feel this kind of absence and most of them will take it as disinterest or - worse - like you’re judging them. BECAUSE OF THE SPOTLIGHT EFFECT. 

So before you start that conversation, take a few seconds and separate fact from fiction using Outcome Independence

What’s the most REALISTIC negative outcome of starting a conversation? 

Maybe the conversation dies out quickly, maybe they don’t message you back...

Unfortunate?

​Yeah. But it’s not a big deal, and it will definitely not destroy your life. 

Compliment someone to start a conversation:

Another great way to start a conversation while sidestepping the Spotlight Effect is to compliment the other person. 

People love feeling good about themselves and giving a compliment is a great way to do that.

Examples:
​

• “I love your shoes! Where did you get them?”
• “Nice leather jacket! I’ve been looking for one too!”
• “That is such a cool watch!”
• “Where do you get your hair cut? I’ve been looking for a new barber.”

Have a Few Topics Ready:

Once you’ve started that conversation, it’s all about keeping it going. The best way to do this is to ask questions. 

Remember this most quoted universal truth - People love to talk about themselves.

So give them the chance!

But you can’t just drill people with questions the whole time or it will start to feel like an investigation.

It’s important to have a few topics prepared on your side as well. 

Think about what’s going on in your life. What are your hobbies? Have you traveled recently? 

Pick a few stories and prepare answers to common questions ahead of time. 

People love to ask things like:

• What do you do for work?
• What have you been up to lately?
• How did you meet your SO?
• Do you come here often?
• How do you know the host?

Having things prepped ahead of time will help you feel prepared and confident. 

How to Start a Conversation While Texting 

​I get a LOT of questions about this from my clients.

You already have their number - now how do you start a conversation by text?

Whether this is a friend situation or a dating/crush situation, the rules are the same. 

1. Have a reason to start a conversation with them!

Especially early in a DM or texting conversation, we want to do most of the heavy lifting. No DMing “Hey, what’s up?”

That is like interrupting someone at home and asking them to entertain you.

Not a good look. 

Try “I saw this and thought of you!” instead. [Insert pic of comic they mentioned liking or a funny sign on the street - something that actually made you think about them.]

2. Keep it light and positive!

The beginning of a relationship should be focused on positive vibes - laughing and building trust.

​Don’t overload your new friend with heavy or political matters just yet.

3. Don’t overload them! Make texts easy to read and respond to! (Whitespace is your friend!) 

A good rule of thumb is the “triple text” rule. Two in a row might be okay - but don’t send three or more all at once! 

4. Send links and/or memes about something you’ve read, or experienced recently.

Example: “Hey have you seen this? I couldn’t stop laughing… [Link]”

Check out this link I sent my buddy who is also interested in baseball:

5. Circle back on a past conversation.

Example: “Hey, you mentioned that you were going back to school, how’s it going this semester?”

How to Make Starting Conversations Automatic:

Once you get the basics of how to start a conversation down, you want to start making it an automatic practice in your life. 

Having the best conversation starters in the world won’t make a damn bit of difference if you can’t build the habit of starting conversations into your daily life.

Something I teach my private coaching clients is to gameplan-out situations where you are likely to have opportunities to start conversations with others (the gym, work, school, meetups, dinner parties, etc.). 
​
Try setting up "If / When / Then" scenarios to guide you. 

• If I am at a party, when I see someone I’m interested in talking to, then I will stand near them, compliment something about them, and ask if they’re enjoying the party.
• If I am in a conversation, when I hear someone mention a hobby, then I will say “That sounds so interesting! Tell me about how you got into that.”

Eventually, you’ll become a conversation starting machine!

Summary: How to Start a Conversation

​Now that we’ve learned how to start a conversation in almost any situation, it’s up to you to put these practices into...well, into practice! 

Here’s a short debriefing to help you:

Action Steps

• Memorize 3 conversation starters from this article to build your confidence.
• Remember that people love to talk about themselves - ask questions!
• Remember the Spotlight Effect - Everyone feels judged a little in social situations!
• Don’t be overly focused on the outcome, just be interested in people and present in the conversation.
• Practice, PRACTICE, PRACTICE!!!! Once this is automatic, people will respond to how natural it feels. 

Next Steps

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