How to start a conversation

Conversation Starters

Here are some great questions for starting a conversation. There are a lot of random conversation starters to get you started and then conversation questions listed by topic. You can start with the random questions or find a topic that interests you. There’s no right place to start, just scroll down to wherever you want and get started!

There are tons of ways to use these questions. I find that the most rewarding way is for everyone to pull up this list of conversation starters on a phone or tablet, and then take turns letting everyone choose a question to ask the group. Remember don’t be afraid to delve deeply into the conversation. Answering the specific question isn’t the goal, having an interesting conversation is!

The title would have you believe that there are 250 questions, but there are actually more. I’m sure you don’t mind a few more questions, right? Dig in and start having some great conversation questions! You can start with the random conversation questions below, or you can skip to questions about a certain topic.

We have questions about movies / books / music / apps / phones / sports / restaurants / travel / technology / clothes / goals / seasons / holidays / education / food we also have some weird conversation questions. And if all those questions still aren’t enough, we have even more questions

The Golden Rule: Be Friendly

Forget about impressing people right off the bat when you start a conversation. You’ll have plenty of time to impress with your slick, charming self. I have one golden rule for starting a conversation and that is to be, or at least appear, friendly.

Your goal is not to impress, it is to show that you are a relaxed and sociable person who wants to have an enjoyable chat. That’s the best way to engage another person in a conversation.

When I work with my clients to help them improve the way they initiate a conversation, we focus on developing a friendly vibe more than anything else. And a friendly vibe is demonstrated mostly by your non-verbals.

So instead of focusing on coming up with clever conversation starters that will instantly woo the other person, focus on:

  • Smiling and holding eye contact;
  • Breathing regularly and relaxing your body;
  • Keeping your posture open and non-threatening.

A Conversation Is a Two-Way Street

I often find that lots of people hesitate to talk about themselves, especially at the beginning of a conversation. They may believe it’s impolite or they may not be comfortable with opening up, so they choose to bombard the other person with questions as an alternative.

Nobody wants to feel like they’re in an interrogatory when they’re having a conversation: What do you do? Where do you live? Where do you work? Where are you from? What hobbies do you have? That is too many questions for two minutes of conversation.

Study people who are able to start conversations with ease in a semi-obsessive-compulsive manner like I did, and you’ll notice they are very open and talkative, and they have something to say about almost anything. This is why I believe that learning how to start a conversation is an exercise in opening up more.

If I were to synthesize how to start a conversation in one concise phrase, it would be this: have a combination of friendliness, curiosity, authenticity and verve. This mix is an almost magical key which opens many doors in social interactions. And more open doors mean more options.

Image courtesy of Batara


Most conversations in English, and in many languages around the world, begin with a greeting. In English you’ll find formal and informal greetings that can be used in various situations.

Formal ways to greet someone include:

  • Hello
  • It’s a pleasure to meet you
  • Good morning/afternoon/evening

Some informal greetings:

  • Hi
  • Hello
  • Hey
  • Yo!
  • What’s up? – this is an informal way to say: how are you?


Questions are an important part of conversational English. It’s polite to ask about another person, to find out more about them, and to get to know them.

Generally when people start a conversation in English with someone they know it’s polite to enquire about how the other person is.

  • How’s it going?
  • Hi, how are you?
  • How’s your day going?
  • Having a busy day?
  • How’s life?
  • How’s everything?

And there are some basic questions that you can ask anyone, anywhere.

  • What’s your name?
  • Where do you live?
  • Where are you from?
  • What do you do?

The type of questions you ask someone in a conversation depend on various factors.

How well you know the person

You would speak more formally to someone you’ve never met, to a work colleague, or to someone older than you. You would speak more casually to a good friend, and to people in your own age group.

It’s a good idea to wait until someone speaks casually with you before you speak casually with them. You may find that people will begin to use casual greetings with you over time, as you get to know each other better.

Someone you’ve just been introduced to:

  • Nice to meet you!
  • Pleased to meet you!
  • How do you two know each other?
  • So, what do you do for a living? – this means what do you do for a job?
  • How long have you been doing that?

Someone you haven’t seen for a while:

  • How are you keeping?
  • What have you been doing lately?
  • How’s your family?
  • Long time no see!

Where you are

If you meet in the workplace, you may want to talk more formally. If you meet in a more casual environment, like at a party, in a bar, at a concert, or at the theatre you can talk more casually too.

Wherever you meet, you can talk about something you have in common. For example, if you’ve met at a party you could ask:

  • How do you know (the host of the party/the person who has introduced you to each other)?
  • Would you like a drink?
  • I love this song – do you like this kind of music?


It’s polite to ask a person questions about themselves when you meet them, but it’s also important to respond to questions they’ve asked you. This helps to keep the conversation flowing.

You can combine your answers with follow-up questions based on information the other person is giving you. For example, if someone mentions they used to live in New York you could say:

  • Oh, you lived in New York? How long did you live there?
  • I’ve never been to New York; did you enjoy living there?
  • I loved visiting New York. Are there things you miss about living there?
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Mirroring, or repeating some of the things the other person has said to you or asked you is a polite and easy way to respond too. For example:

  • Hi, I’m Anna. It’s nice to meet youHi, I’m John. It’s nice to meet you too
  • Hi, I’m Anna. Are you enjoying the party?Hi, I’m John. Yeah, it’s been great! Are you enjoying it too?

Wrapping Up How to Start a Conversation With a Girl

Once you know how to start a conversation with a girl (and do it consistently), you’re dating life will drastically improve.

You’ll meet more women you have chemistry with, go on more dates, and improve your conversation skills. You’ll also build up the reference experiences you need to improve your confidence and level up in all aspects of life.

To recap, here are the 7 tips for how to start a conversation with a girl:

  1. Increase your awareness of beautiful women
  2. Be comfortable with your fear
  3. Don’t hesitate
  4. Have some conversation starters in your back pocket
  5. Get through the initial awkwardness
  6. Know how to bridge the conversation
  7. Assume attractionBonus tip: Learn to recognize and listen to your “gut feelings”

So get out there and start putting these tips into action!

And if you want more help with starting conversations and flirting like a pro, check out my brand new free video course on conversation and flirting! Just click the link below and enter your email to get instant access to the first video:

Click HERE to get instant access to my free video course on conversation and flirting

Here’s what you can say:

  1. “You seem pretty stressed and tired these days. Something wearing you down?”

  2. “You haven’t seemed like yourself the last few weeks. Is anything up, maybe something I could help with?”

  3. “No matter what’s bothering you, I’m all ears. Don’t worry, I’m not here to judge you.”

  4. “I just want you to know that I have your back, whatever’s going on I’m open to helping out in whatever way I can.”

  5. “All this stuff is actually pretty common among men – it’s nothing to be ashamed of.”

  6. “I’m not an expert when it comes to this kind of thing, but there’s a site called HeadsUpGuys. It has lots of practical tips for dealing with stress and depression. Here I can show you…”

  7. “There’s a self check on this site called HeadsUpGuys, maybe try taking it and you can get a better sense of how you’re doing?”

  8. “I hate to see you down like this. You know if you’re not feeling right, there’s no shame in seeing a doctor and getting their advice.”

Get more tips on how you can provide initial and ongoing support for a guy you care about.

How to Get Over the Fear of Starting a Conversation in English


Before we get into the thick of things, I’ll let you in on the mindset you need to have when starting up a conversation.

The fear of speaking to strangers really comes from the fear of seeming “weird” or looking foolish. You're essentially afraid of the other person’s reactions, like a strange look that says “I don’t want to talk to you”, or even someone laughing at you. (Of course, this very rarely happens in real life!).

To be honest, I still experience moments of fear when I start conversations in a language I’m learning. It sometimes takes me a few minutes to get into the flow. Just know that this feeling is totally normal. Try to accept it as normal, and not to worry about it too much.

Step 1: Be Friendly!

The first key to feeling relaxed and getting over your fear is to have a good time and be friendly. Smile and enjoy the experience of meeting someone new. If you can relax and enjoy getting to know someone, then that will be felt by the other person and it will put them at ease.

Talking with someone who is super serious and has a grave expression is rarely enjoyable, so why put someone else through that? Relax your face and turn that frown upside down!

Talk to people as you would talk to a friend, and they may just become one.

Step 2: Take the Pressure Off

A lot of fear around starting conversations comes from putting pressure on yourself to have a certain result from the conversation.

So, stop having specific expectations about what will happen! Whatever happens happens. Don’t expect anything from yourself or the other person other than getting to know them a little better.

Also, don’t force a topic or be aggressive in what you’re trying to say. That type of energy is a turn-off to someone you’ve just met. Let the conversation flow naturally.

Finally, realize that you don’t need to become BFFs (“Best Friends Forever”) with your conversation partner. There are millions of native speakers out there, so becoming friends with this one person won’t determine your success as an English speaker. If the conversation doesn’t go well, that’s okay. The next opportunity is just around the corner.

Step 3: Remember, the World Doesn’t Revolve Around You

Don’t make the conversation only about yourself. Try to ask questions about the other person’s life. Only interject things about yourself when they are actually relevant to the topic.

What if they ask you a question about yourself? Answer it. But then ask them the same question. Often people ask questions they secretly want to be asked themselves, so turn the question around and see what your conversation partner has to say.

The most important thing is to not be forceful or seem desperate. Bring things up naturally and casually. People should never feel pressured to talk with you, so help them feel comfortable.

Step 4: Be Honest

When asking questions or talking about something, don’t make something up just because you memorised a particular phrase.

For example, don’t say “I love cats too!” if you actually hate cats. Or avoid saying “My uncle works in a factory” when you don’t even have an uncle, let alone one that works in a factory.

Make sure you say things that are true, even if it means searching for the words you need. Otherwise you could end up in a really awkward situation.

Step 5: Avoid Closed-Loop Questions

Questions that can only be answered with “yes” or “no” are what I call closed-loop questions, because they close down conversation. Open loop questions work much better when your aim is to keep a conversation going.

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Let’s look at the difference between these through a couple of examples. Instead of asking the closed question “Do you like apple juice?”, ask the open question “What is your favourite type of juice?”

Or, instead of asking “Do you like spaghetti?” you can ask “How often do you eat Italian food?”

Open-loop questions invite further discussion, whereas a “yes” or “no” question usually just invites an end to the conversation.

Now that you have the right mindset, let’s get into what you can say to start up and maintain some great conversations.

Joining and Talking in a Group Conversation

Not all your conversations are going to be a one-on-one encounter. Sometimes you will be joining a group where others are talking.

The most important skill in group situations is listening. Pay attention to the conversation and interject only when it is relevant.

Many of the phrases you’ve learned so far in this article can work in group situations. You can also add to a group conversation with other types of phrases, such as sharing your experiences or thoughts, asking questions to the group, or making connections between two people.

Here are some phrases you can use:

Sharing Experiences or Ideas


If you have something to add to the conversation, here are a few examples of how you can do it:

  • “Actually, that happened to me once. It was really [annoying].”
  • “I totally agree. The same thing happened to me too.”
  • “That’s pretty common. I heard that a lot of people had the same experience.”

You don’t need to share too much, but let the group know that you have more information to add. If they want to know more, they can ask for details.

Asking Questions to the Group

If you notice that some people in a group aren’t participating as much in a conversation you can ask questions for the whole group. Here are some questions to stimulate more dialogue:

  • “Has anyone ever … ?”
  • “How many of you think that …?”
  • “Do a lot of you … ?”
  • “Which one of you … ?”

Or, you can direct it to an individual. Just be sure not to single them out in an uncomfortable way. Here are some examples:

  • “What do you think [Diana]? Has that ever happened to you?”
  • “Hey [Carlos]. Didn’t you also … ?”

Making Connections Between Two People

You may realise that two of the people in the group have something in common. You can make people feel included and connected by sharing these observations with the group. Here are some ways to do it:

  • “Actually, [Navvab], didn’t you go there last year too?”
  • “You should ask [Samson] about that. He had the same thing happen to him.”
  • “[Makoto] has the same phone! Where’d you get yours [Makoto]?”

This can help people feel like a part of the group. Of course, don’t let out anyone’s secrets!

Closing the Conversation or Leaving the Group

If you have to get going and want to excuse yourself from the group, here are some quick and easy ways to do so:

  • “Hey, I better get going. I have a long day tomorrow.”
  • “Hey Guys. Sorry, but I have to run. It was great chatting with you all.”
  • “Oh man, it’s getting late. I better head out.”
  • “Alright guys. Time for me to go. Have a good one.”

Conversation Starters in Context: On Location

Often what you say directly relates to where you are.

Whether you're in a restaurant, the airport or on the job, you should have some phrases handy to start up a conversation that relates to your location.

In a Restaurant or Cafe

Here are phrases and expressions you can use to start and maintain a conversation in a restaurant or cafe:

  • “Do you have a recommendation on any good dishes?”
  • “What would you recommend for someone who hasn’t eaten here before?”
  • “What is the best drink here?”
  • “Do you know if the [chow mein] is any good?”
  • “Have you ever had the [asparagus]?”
  • “If you had to eat just one meal for the rest of your life, what would it be?”
  • “What is your favourite dessert?”
  • “What is your favourite spicy dish?” (They don’t like spicy? Great! Ask them why, and keep the conversation going.)

Finally, here are some phrases you can use at the end of your conversation:

  • “Enjoy your pasta!”
  • “Have a good meal!”

In Someone’s Home

If you’re visiting someone’s home you’re in luck! There are an endless supply of possible things to talk about. Just look around the house and you’ll see many things to bring up and discuss.

  • “How long have you lived here?”
  • “Where did you get this [bookshelf]?” (or television, chair, porcelain fountain, etc.)
  • “What is your favourite thing about this house?”
  • “How many people live here?”
  • “How many rooms does this house have?”
  • “Is this house close to [your work]?” (or school, or the park, or the airport, etc.)
  • “How far away is the [supermarket]?”

And here are a few home-specific statements that you can say when leaving someone’s home:

  • “Thank you for having me over!”
  • “Thanks for inviting me to your home.”
  • “I had a wonderful time.”

In the Street

Sometimes you bump into someone when you are out and about. They might be sitting on a park bench, or waiting in line at the bus stop. Here are some questions and statements you can use to start and keep up a conversation:

  • “Do you know where a [bakery] is around here?”
  • “What street is this?”
  • “Do you know what time [bus 37] comes by?”
  • “Where can I buy a [bottle of water]?”
  • “What is your favourite thing about [this park]?”
  • “How crowded are the buses when they get to this stop?”
  • “Can you recommend a good restaurant around here?” This can be followed by “What is your favourite dish there?”

At the Airport

From personal experience I know that airports are often a place where you have to “hurry up to wait”. You rush through customs or security only to sit at the gate waiting for your plane for several hours (or longer if it is delayed). This is a great chance to chat to someone in English. Here are some phrases that can get things started:

  • “Have they announced the boarding time for this flight?”
  • “Is there a place to charge a phone nearby?”
  • “So, where are you headed today?”
  • “Do you know what time we arrive at the destination?”
  • “Is this your preferred airline?” followed by “why is that?”
  • “Are you flying home or are you flying away from home?”
  • “Where is the favourite place you’ve ever visited?”
  • “Have you ever had the chance to fly in first or business class?” then “what was it like?”
  • “Can you recommend any good restaurants or sights in [Buenos Aires]?”
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Because you’re flying somewhere, odds are you will never see your conversation partner again. That means you don’t have to worry about making a fool out of yourself because your connection with them will be short lived and temporary. Plus, there is a good chance someone you talk to may have some great suggestions about places to see or things to do in your destination city.

On the Job

If you’re working among English speakers, then this is a perfect chance to strike up a conversation. After all, you already have something in common! Here are some phrases you can use to start up a conversation with a work colleague:

  • “How did you come to work here?”
  • “What is your favourite place to eat lunch near the office?”
  • “What do you enjoy most about your job?”
  • “What is your eventual career plan?”
  • “What do you think is the most important thing to succeed in this company?”

At School

You may be a student and find yourself surrounded by English speaking students, or perhaps there is an English speaking student at your school. Why not get to know them better? Here are some questions you can use:

  • “How long have you been a student here?”
  • “What are you studying?”
  • “What do you recommend to eat on campus?”
  • “Do you know a good, quiet place to study?”
  • “What do you plan to do when you finish your studies?”

As you can see, you really can make friends anywhere, and you should never be at a loss for a way to start up a conversation.

Conversation Starters: Events


You’ve been invited to a special event and want to be able to start up a conversation with the people there. The wonderful thing about events is that you automatically have a point of common interest. Just explore that common thread further to weave a full tapestry of interesting conversations.

At a Birthday Party

A birthday party is a fun place to get to know someone and it’s really easy to start speaking with a total stranger. Here are some phrases to help you get going:

  • “How do you know [the birthday person]?”
  • “What do you think of the [birthday cake]?”
  • “What is the best birthday party you’ve ever been to?”
  • “If you could re-live any year of your life, which one would it be?”
  • “When is your birthday?”

At a Wedding

The joining together of two people in marriage is a joyous event, and while you’re there throwing confetti and dancing the Conga, be sure to sit down and have a chat with someone new! Try out these phrases to help break the ice:

  • “Are you a friend of the bride or the groom?”
  • “Whats the best wedding you’ve ever been to?”
  • “If you were going to plan the perfect wedding for your best friend, what would it be like?”
  • “Do you like dressing up in formal attire?”
  • “Do you know where they are going on their honeymoon?”

At a Sporting Event

A match or game can be a perfect opportunity to make some fast friends. Connecting with others who share a passion for sport seems to automatically create a bond between people.

Here are some questions you can ask at the next big game:

  • “Who do you think will win?”
  • “Have you been following all the matches this season?”
  • “Who is your favourite player?”
  • “Do you play the sport yourself?”
  • “What do you think the score will be?”

At a Concert or Performance

Music fans love seeing their favourite performers on stage. If you have tickets to an event or are just sitting in a cafe watching someone strum a guitar, be sure to strike up a conversation with other music enthusiasts near you.

  • “What’s your favourite song of theirs?”
  • “Do you play music yourself?” or “Do you play an instrument?” or “Do you sing?”
  • “How often do you go to a show?”
  • “What do you like about this performer?”

Be Friendly, Considerate, and Open Your Mouth!

There you have it. One hundred and twenty five different ways to strike up a conversation and keep it going strong.

Sure, it can be intimidating when you consider talking to a total stranger. Especially when they speak a different language than you. Getting over your fears is the first step, not only in language learning, but in being able to meet fascinating people and make long-lasting friendships.

Just remember these main points:

  • Be friendly! — Even if the other person doesn’t have time to talk, at least they’ll appreciate your pleasant demeanour.
  • Take the pressure off — When you come in with expectations you may become easily disappointed. Just have fun and let whatever happens, happen!
  • Talk about them — They don’t want to hear your life story (At least not yet). Ask them questions that show you want to get to know them better, and they’ll probably reciprocate with the same.
  • Be honest — No need to make up an impressive story to get someone’s attention. Just be yourself and tell the truth.
  • Ask open loop questions — A “yes” or “no” can be a conversational dead end. Ask questions that spur on further discussion.

We’ve covered a lot of potential situations and questions or phrases you can use in each one. But whether you use these approaches or just throw on some random accessories, the goal is to speak at every opportunity.

You’ll notice I didn’t say the goal is to talk for 15 minutes. And I didn’t say the goal is to bring up a specific topic. The only goal is to open your mouth and start talking in your target language.

Getting a conversation started is the biggest hurdle. It is the one action that will have the most significant impact on your language learning (and friend making) success. Be open to whatever happens from that point forward and you will multiply your chances of improving your English.

*Lee este articulo en espanol aqui!(Read this article in Spanish here!)

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