55+ Ways To Start A Conversation (Examples For Every Situation)

By Sky Ariella - Nov. 15, 2021
Skills Based Articles

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Few situations increase anxiety more than starting a conversation, especially wtih someone new. But we also know that conversation is the foundation for building and maintaing connections with the people around us.

Whether you’re looking to improve your communication skills on a first date or just want to improve your likability to strangers, the following conversational tips can help.

What Kinds of Conversation Starters Are There?

The kind of conversation starter that you use changes depending on what the situation is. When you’re starting a conversation with a colleague at work, you take a different approach than catching up with an old friend you’ve known since elementary school.

Considering the dynamic with the other party and situation is crucial for using an effective conversation starter.

General Conversation Starters

Some situations don’t fit into a work or dating context, making it tough to decide what conversation starter to use. Imagine being on a long plane ride next to a stranger or going out to lunch with an acquaintance. That’s what these general conversation starters are for.

  1. What’s Your Story? This question leads to an answer that gives you a better idea of who a person is. The topics they choose to focus on say a lot about them, and it’s easy to find more dialogue to branch off this conversation starter.

  2. Have You Been Doing Anything Exciting Recently? This conversation starter works because it allows the other party to talk more about their current passions.

  3. Do You Have A Favorite Book? Since not everyone is an avid reader, this question is open-ended enough to appeal to any type of person. Even if they don’t have a favorite book, they’ll probably follow up with another type of media they enjoy.

  4. Do You Have A Favorite TV Show Or Movie? This question is similar to asking about a person’s favorite book and can be used interchangeably to engage in dialogue. Choose whichever topic you enjoy speaking about more.

  5. How Would You Describe Yourself? Asking a person to describe themselves is a great way to learn more about them and open up a deeper conversation.

  6. Are You Doing Anything Fun This Weekend? This is an easygoing conversation starter, which will likely lead to some back and forth involving what you each have planned.

  7. What Was The Best Part Of Your Week? Positive conversation makes people want to keep it going. Speaking about the best things that happened in a given week is an enjoyable and recent topic to discuss. That makes this question a great conversation starter.

  8. Have You Been Busy Recently? Asking about a person’s recent activities is a neutral opener that can get them talking about things that are important to them at the moment.

  9. What Do You Like To Do For Fun? People enjoy speaking about their interests and hobbies, so posing a question about these topics is an excellent way to start a conversation.

  10. Where Are You From? Asking about where someone is from allows them to give a brief overview of their history, such as parts of their hometown they like spending time in.

  11. Do You Have Pets? People love their furry family just as much as their human one. If you’re an animal person, asking about the other party’s pets is a great way to start a conversation.

  12. Conversation Starters for Work

    Being at work requires a professional filter for the conversation starters you use and a heightened focus on networking. The following examples can assist in achieving rapport with co-workers.

  13. What’s Your Favorite Thing About Working In ______? Everyone has their own motivations for why they went into their professional field. Discussing it can be an interesting conversation in the workplace. It can also bring up commonalities between you and your co-worker’s passions.

  14. What Do You Like About Working Here? This question seeks clarity into what your co-workers enjoy working at your company. It can spark a productive back and forth about what your team does well and where you can improve.

  15. Do You Need Help With That Task? Offering your help with a difficult or even minor task improves your rapport with co-workers and lets them know that they can rely on you.

  16. How Was Your Weekend? This is a good conversation starter to become friendlier with your colleagues, without prying too much into their social life.

  17. Have You Heard About ___ On The News? The ulterior purpose of the nightly news is to give professionals topics to use as conversation starters. Just make sure the story you choose to discuss isn’t too controversial or inappropriate.

  18. What’s Your Favorite Food? You can use this question to segway into asking if they’d like to join you for lunch. Building a strong network of colleagues you get along with is essential for career advancement.

  19. Are You Looking Forward To (The Nearest Holiday)? While this question can be a little tricky because you don’t want to impose religious beliefs on your co-workers, it can help you get to know them better.

  20. I Love Your (Accessory Or Clothing Item)! Giving a sincere compliment makes the receiver feel good about themselves. This can be a great way to start up a conversation with a coworker.

  21. Can I Ask You For Some Advice? The purpose of working with a team of colleagues is to turn to each other for help and guidance. Asking someone for advice on something related to your job can lead to a more secure and productive professional relationship.

  22. What Did You Think Of The Last Meeting? Discussing work meetings fosters brainstorming after the fact, and it can be an excellent conversation starter.

  23. How Was Your Vacation? When a co-worker returns from a vacation, they come back with numerous stories to tell. Asking briefly about their vacation can kick start an enthusiastic conversation.

  24. Conversation Starters for Dates

    Most people get a little nervous before embarking on a first date because of the dreaded uncomfortable silence that could pop up when eating a meal with a stranger. Posing some of the following questions and topics can help boost the conversation on a first date.

  25. What Kind Of Work Do You Do? People spend a huge chunk of their time working throughout their lives. Having a date walk you through their occupation and why they’re passionate about it teaches you a lot about who they are.

  26. Which Of Your Family Members Are You Closest With? This is a covert way of learning more about a person’s family, values, and what qualities they look for in the people they keep close. It can also create a deep and meaningful dialogue.

  27. What Do You Like To Do For Fun? How a person enjoys spending their free time will tell you a lot about their personality.

  28. Where’s The Best Place You’ve Traveled To? Asking a date about their former travels is a great conversation starter because the topic usually comes with a lot of potential stories you can share with each other.

  29. What’s Your Favorite Local Restaurant? This is an effective ice-breaker to use because it tells you what kind of food they like and gives you a suggestion for where to take them on a second date.

  30. What’s Your Most Niche Interest? Most people have that strangely specific interest that they know a lot about, and asking about your date’s can send them talking on a spree.

  31. Do You Prefer Going To Concerts Or Listening To An Album At Home? This question is a subtle way of asking whether your date is an introvert or an extrovert. It can also spark a conversation about your favorite music artists and concerts you’ve attended.

  32. How Do You Destress At The End Of A Busy Week? Answering this question will usually involve talking about activities that bring joy, which is a good tone to set for a first date.

  33. Do You Have Any Fears? Most people are scared of at least one thing in the big and broad world. Whether their fears are small, like spiders, or much grander, such as failure, it will likely lead to an interesting conversation.

  34. Tell Me About The Best Day Of Your Life, So Far. This question may leave your date speechless for a moment, but once they come up with a response, it will be a conversation that sticks with them long after it’s finished.

  35. What Did You Want To Be When You Grew Up As A Child? Asking your date about their childhood dreams will tell you a lot about them as a person and start an engaging conversation.

  36. How Would Your Friends Describe You? This is a popular question in job interviews because it illustrates a candidate’s self-awareness and perspective. You can use it as a conversation starter on a date for a similar reason and learn more about their friend circle.

  37. Conversation Starters for Children

    Communicating with children is different than it is with adults. They make it clear when they’re uninterested and require consideration for age. Refer to the following conversation starters the next time you’re speaking with a child.

  38. What’s Your Favorite Game Or Toy? A huge part of childhood is getting time just to play. Asking about a child’s favorite game or toy is an excellent way to break the ice with them.

  39. What Was The Best And Worst Part Of Your Day? Children have highs and lows to their day, just like adults. Asking about what their positive and negative experiences in the day were gets them talking freely.

  40. How High Can You Count? Depending on a child’s age, this question can be an excellent way to get a child involved in the interaction and showing off their knowledge.

  41. What Job Do You Want When You Grow Up? Most kids have been asked what they want to be when they grow up at some point in their young lives, making it a topic they’re familiar with and will usually speak openly about.

  42. Do You Think There Are Aliens In Space? This is a fun question that can lead to a fascinating dialogue between an adult and a child.

  43. What Is Your Favorite Day Of The Week? Asking about a child’s favorite day of the week may land you with some surprising answers.

  44. What’s Something That Annoys You? Engaging a child in a discussion about the kinds of behaviors that bother them gives them the confidence to speak up as they get older and can teach you more about them.

  45. Tell Me About A Good Memory You Have. A child’s creative imagination may take this question to fascinating places and develop a strong dialogue.

  46. What Animal Noises Can You Make? This is another example of a conversation starter that gets children involved in a fun way that demonstrates their knowledge.

  47. Do You Like Summer Or Winter Better? Using this conversation starter works well with younger children because it gives them an option to choose from. You can then elaborate on whether they like summer because it’s hot or winter because they enjoy the snow.

  48. Do You Know Any Funny Jokes? This question works well with children because they’ll probably give you a humorous answer even if they aren’t familiar with any pre-written jokes.

  49. Conversation Starters for a Party

    Large events and parties have a lot of action coursing within them, which can actually make it more challenging to build intriguing conversations with people. Consider the following conversation starters to use at a party.

  50. What’s The Title Of This Chapter In Your Life? The unique thing about this question is it’s a common topic wrapped up in unusual phrasing. Perfect for a party.

  51. What’s The Worst Movie You’ve Ever Seen? This takes a comical twist on the classic question of what someone’s favorite movie is.

  52. What Is Your Guilty Pleasure? Whether you still enjoy listening to Backstreet Boys in secret or watching trashy reality TV shows every Sunday, everyone has a guilty pleasure, which can be an amusing topic to talk about at a party.

  53. How Do You Know The Host? This is one of the easiest questions to begin a conversation with at a party. Finding out how they know their connection to the party can lead to other interesting questions.

  54. What Was Your News Year’s Resolution This Year? Did You Stick To It? Using this conversation starter might land better near the holiday season, but it can bring up a compelling conversation about the nature of yearly resolutions either way.

  55. If You Could Choose A Different Career Path, What Would You Pick? While many people are happy in their jobs, it can still be a striking conversation starter to pose what they would’ve done otherwise.

  56. Teach Me Something. Everyone’s an expert on something, and asking someone to teach you a fact or trick at a party can be an excellent way to get the conversation ball rolling.

  57. Who Was Your Favorite Teacher In School? Throughout school, most people have at least 12 different teachers. Asking about someone’s favorite at a party will likely lead to some nostalgic stories.

  58. What’s The Best Advice Anyone Has Ever Given You? Ask this question to somebody at a party when you want to know more about their goals and outlook on the world. Or when you’re just gathering trinkets of advice from strangers to turn into a self-help collection.

  59. Which Animal Do You Think You’re Most Similar To? Identifying closely with an animal can actually give a lot of information about a person’s character. For example, if someone explains that they identify with a dolphin, it might be because they’re smart and kind.

  60. If You Won A Million Dollars Right Now But Had To Spend It All In One Day, What Would You Buy? This question delves into what the answerer likes to do without the contingencies of the future or the restrictions of reality.

    A person who responds that they’d buy clothing enjoys different things than someone who would book a vacation. It’s a hypothetical scenario that gets the creative juices flowing.

  61. Do You Have Any Tattoos? Tattoos tell a story through art. Asking about a person’s tattoos can be a great way to open a conversation about their stories, values, and passions.

Conversation Starter Categories

So far, we’ve split conversations up by social context. Let’s take a look at more general categories of conversation starters that can work across contexts and conversational partners:

  • Find commonalities. Looking for commonalities is a great way to kick off conversations with people you don’t know well (or at all). This can range from a shared friend, a passion for the same hobby, or even just a love of the same TV show or sports team.

    A big part of the anxiety we experience around new people centers on worrying that we have nothing in common and so we’ll be seen as boring or unworthy of talking to. But if you take the time to ask, you’ll find you have more in common with the people around you than you might imagine.

  • Pleasant observations. Compliments fall under this category, but not exclusively. Plus, compliments can be a tricky thing to pull off with new people when you’re not sure how your comment will be received.

    Safer observations involve the immediate world around you or an experience you just shared. Talking about your favorite parts of a movie you just watched, pointing out how nice the sunset is, and mentioning that today’s meeting was particularly useful are all nice things that can lead to a positive conversation.

  • Learn more background. This category is more for new people, but sometimes we know shockingly little about even the coworkers we spend hours around. Taking the time to learn more about someone’s background (where they grew up/went to school, what their last job was, places they’ve lived, etc.) can help us make the characters in our life a bit more three-dimensional.

    Plus, most people enjoy telling the highlights of their life, and there are a million little side paths that a conversation like this can go down. It also invites reciprocal questions, so you’ll likely leave the conversation with someone knowing a bit more about you as well.

  • Soliciting an opinion or information. Asking for someone’s opinion, advice, or just the facts of a situation is a great way to show that you respect what they have to say. People generally feel safe around topics that they have an expert knowledge of as well, which promotes a relaxed and comfortable atmosphere.

    Likewise, asking for information gives your conversational partner something definite to respond with, another thing people appreciate.

  • Minor griping. Most of us enjoy complaining to some extent — it feels good to vent about the minor annoyances in our lives.

    Kicking off a conversation about the “great weather” when it’s lashing rain, the never-ending workload of the holiday season, or the painful awkwardness of a party, for example, can make you and your conversational partner feel like instant war-buddies who are both just dealing with it the best you can.

    Warning: don’t lean too heavily on complaints for your conversation starters. They have their place in the fabric of the human experience, but nobody wants to hang around someone who is eternally negative. And if you do kick off a conversation with a bit of griping, try to bring things to a more positive place when you can.

Tips for Keep a Conversation Going

Starting a conversation may be simple enough, but keeping it going is another story. Below are some tips to help you maintain a conversation once you’ve started it.

  1. Be Confident. People in any social situation respond well to respectful confidence. Displaying this in an introductory or in-depth conversation is likely to strengthen it.

  2. Listen To The Other Person. The best thing to do when trying to establish an engaging conversation is listening to the other party. It gives you related topics to work from and demonstrates that you care about what they have to say.

  3. Think About Questions In Advance. While you shouldn’t go into a casual conversation overprepared, it can be helpful to think about questions in advance.

  4. Don’t Overshare. This is more important in a professional situation, but can also be relevant when you’re on a first date. Try to keep stories and personal details within appropriate boundaries; otherwise, you run the risk of the other person checking out.

  5. Don’t Worry Too Much. The worst thing that is going to come from a casual conversation you start is an awkward silence. That may seem like the end of the world, but it’s not. After a few awkward pauses, you learn to appreciate them as it means you’re getting more comfortable with the person you’re talking to.

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Author

Sky Ariella

Sky Ariella is a professional freelance writer, originally from New York. She has been featured on websites and online magazines covering topics in career, travel, and lifestyle. She received her BA in psychology from Hunter College.

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