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A Trusted Friend in a Complicated World

40 Conversation Starters That Make You Instantly Interesting

Never struggle to make small talk again.

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Conversation starter: Ask for a helping hand

“Helping questions are great conversation starters because when a person helps you it forms natural bonds. When you help another person to figure what an item is on the buffet or locate the restroom, it lowers your defenses. For example, if you’re at the grocery store, ask ‘Do you know how to tell if this fruit is ripe?’ It makes you look open to learning more and will help the conversation flow naturally.” Dawn Maslar, MS, author of Men Chase, Women Choose: The Neuroscience of Meeting, Dating, Losing Your Mind, and Finding True Love. These magic phrases can save any awkward conversation.

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Conversation starter: Compliment something other than someone’s looks

“Instead of complimenting something generic like their eyes, highlight something that shows their personality, like their purse or a book. This is simple, elegant, and great if you are interested in someone or anytime you want to boost their likability toward you for business or social reasons.” —Paul DePompo, PsyD, ABPP, psychologist. Check out these tips for giving sincere compliments.

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Conversation starter: Bring up a shared interest

“Many people think they have nothing in common with a stranger but if someone is at a grocery store, restaurant, or bar they are there for a reason—one which is likely similar to yours. You’re both there so you both share a common interest. Ask questions to find out what that interest is. For instance, ask about what their experience at that venue has been like or why they chose it.” —Shannon Battle, licensed professional counselor. Watch out for these rude conversation habits to stop ASAP.

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Conversation starter: Go simple…yet bold

“Give a genuine smile and say, ‘Hi.’ It sounds too simple but people are so used to other people staring at their phones that a simple smile and hello can be a very bold move. It shows the other person that you’ve noticed them and you’re interested in getting to know them better. And you’ll almost always get a hello back. (If you don’t, let it go. You don’t want to date a rude person anyway.)” —Suzanne Casamento, dating expert and the creator of Fantasy Dating.

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Conversation starter: Ask for their honest opinion

“Asking ‘I’ve been really thinking deeply about something and wondering if I can share it, and get your feedback?’ shows your interest in the other person and solicits new and interesting information that is fun to discuss. Pretty much anyone will want to share their opinions with an interested party and they will think you are nice and fun to be with, as well.” —Melissa Orlov, therapist and author of The Couple’s Guide to Thriving With ADHD. Here’s what expert minglers do naturally to make small talk.

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Conversation starter: Tell a bonding joke

“Jokes work well because they are disarming and work on a biological level. If a woman laughs at a man’s joke, he feels assured that she has a level of comfort with him. For her, laughing releases oxytocin, the ‘bonding hormone.’ These two things together create an opening for more conversation.” —Dawn Maslar. Here are 30 pick-up lines for guys that are sure to make him laugh.

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Two Friends Chatting While Shopping In Clothes Store TogetherTom Werner/Getty Images

Conversation starter: Give an out-of-the-blue compliment

“I always tell my clients to try out a compliment. It breaks the ice and these days it’s completely unexpected! You can test out doing this by just giving people walking down the street a compliment and see their reaction, most times people will give you a smile and possibly engage in more conversation. After all, who doesn’t like to be complimented?” —Stef Safran, a matchmaking and dating expert in Chicago and owner of Stef and the City. Give these funny, punny compliments a try.

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Conversation starter: Get (pop) cultured

“Make a comment or joke about something big in pop culture that most people would be familiar with—something light, NOT political. If you need ideas look at what’s trending or are hot topics on Twitter or Facebook.” —Stef Safran. This sounds like the perfect idea for finding conversation starters at a party—here are some more tips for joining the conversation without being awkward.

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Man in wine shop helping customer reach wine bottle on top shelfZero Creatives/Getty Images

Conversation starter: Ask a fake favor

“People love to help so asking for a small favor is a great conversation starter. If you don’t have a favor to ask for, just make one up. Ask the person you find attractive to help you reach something on a high shelf or hold something while you look through your wallet. At the very least you’ll end up with a fun story to tell your friends.” —Suzanne Casamento. Need to know how to be more articulate? Try these 8 must-follow tricks.

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People waiting in line at theater using cell phonesGranger Wootz/Getty Images

Conversation starter: Make them your accomplice

“This can be as simple as waiting in line at the post office and saying something like, ‘You ready to go rogue? Let’s start another line so we can get this thing going.'” —Shawn Schweier, relationship coach and founder of Alter Shift. Here are 6 polite ways to end a conversation.

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Mature Couple Speaking With Supermarket Clerk While ShoppingTommL/Getty Images

Conversation starter: Show your silly side

“Asking a question with a little humor is a great move. Say you’re in a grocery store, ask, ‘This is very important: What is the best apple ever? Granny Smith or Red Delicious?'” —Suzanne Casamento. This is why it’s good news if you and your partner laugh at the same jokes.

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Conversation starter: Invoke Ikea or the Queen of England

“My favorite conversation topics are something relevant yet funny. My favorite at an event is ‘I just came here for the free Swedish meatballs, why are you here?’ If I’m meeting someone new, I like ‘You look really familiar. Did you and I attend the same private dinner at the White House with the Queen of England?'” —Nicole DiCristofaro, dating and relationship coach at Here are some tips to try for meeting new people.

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Conversation starter: Use a self-deprecating line

“A self-depreciating line is a good opening when someone is engaging in a positive type task and you comment on it. For instance, ‘I’m jealous that you are so good at that!’. This can actually show confidence because you are not trying to appear like you’re awesome.” —Paul DePompo

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Conversation starter: Tell a really dumb joke

“My favorite conversation topic is to say, ‘OK, I’ve got a dumb joke, not a good joke, just a dumb joke for you.’ People are usually more receptive to dumb jokes because it doesn’t require much effort and they don’t have to worry about not getting it. Need an example? What does a fish say when it runs into a concrete wall? Dam!” —Hunt Etheridge, dating and relationship expert. Get some inspiration with these 175 bad jokes everyone will laugh at.

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Conversation starter: Blow their mind

“Most people enjoy trivia, facts, and riddles and they’re also a good way to keep the conversation going over an extended period of time. You can drop in and ask someone ‘What are the only three countries that start with J?’ [Jordan, Japan, Jamaica] or ‘How many state capitals are west of LA?’ [Six. I wouldn’t believe it either until I saw a map] or ‘What starts with “e” and ends with “e” and contains only 1 letter?’ [envelope]. Then circle back with them later to see if they have an answer. They’ll be thinking about it—and you—all evening.” —Hunt Etheridge. Try some of these 100 fun facts about practically everything.

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Two Students Talking To Each Other While Studying In LibraryTom Werner/Getty Images

Conversation starter: Get deep

“Try using a light philosophical twist to an opening such as when you see someone enjoying a coffee you can highlight the beauty in the moment. Say something like, ‘Isn’t this what’s it’s all about?’ This is good for getting to see if this person is open and up for talking without making it seem like you are trying too hard.” —Paul DePompo. 

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Conversation starter: Ask a question with no right or wrong answer

“Asking someone ‘Where are you from?’ is great because it’s a simple and natural way to begin to ask someone about themselves. Any question that is open-ended will work because everyone has a different answer and there is no right or wrong answer. It can become exciting if you both realize you are from the same place or like the same things.” —Simon Marcel Badinter, radio personality and relationship expert. Or if you’re feeling really gutsy, give one of these funny, cheesy pick-up lines a try.

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Mature Businessman In Discussion With Colleague During Commute To Work Thomas Barwick/Getty Images

Conversation starter: Take advantage of the situation

“One of the best ways to start a conversation is to ask a question, and questions germane to the situation are best. For example, if you’re at an event, ask ‘Have you heard this speaker, band, or author before?'” —Dawn Maslar

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Conversation starter: Use a movie quote

“No one knows more about starting conversations and conversation topics than screenwriters. That’s what we do: throw people together, usually strangers, and find a way to get them talking. So I can tell you the best conversation openers in movies are ones that ask a question, tease, and reveal some amazing (or weird) truth about yourself. My favorites are ‘I’m working on something that’ll change the world and human life as we know it!’ from The Fly and ‘Garbage. All I’ve been thinkin’ about all week is garbage’ from Sex, Lies and Videotape.” —Murray Suid, screenwriter and co-founder of Or school them on these 15 movie quotes everyone gets wrong.

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Conversation starter: Make a bet

“Walk up to someone and tell them you need them to settle a bet between you and your friend. For instance, say ‘Can I get your help with something? You see, my friends and I have this bet going on and we need an outside perspective. My friend says that the moon is its own planet. I say that the moon isn’t its own planet.’ Now, obviously, the moon isn’t a planet. Everyone should know that including this stranger you just asked. But it gives you a great in to start a conversation.” —Chris Seiter, author of Ex-Boyfriend Recovery

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Conversation starter: Offer to help them

“Being helpful is always a great way to get a person’s attention, especially when they are struggling to do something or seem overwhelmed. The one thing people always enjoy is relief but you don’t want to add to their stress or come across as creepy. So try something simple like offering to hold something for them.” —Alexis Nicole White, author and relationship expert. 

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Conversation starter: Disarm them with your vulnerability

“Sometimes the quickest way to make another person comfortable is to be vulnerable yourself. At a cocktail party? Tell the person next to you, ‘I don’t know a soul here. It’s so hard to talk to strangers.’ On a flight? Tell your seatmate, ‘Flying makes me a little nervous.’ Folks are more likely to connect with you if you are real, authentic, flawed like the rest of us.” —Jacqueline Lewis, founder of the World Gratitude Map, a crowd-sourcing project and online map that encourages users to document and celebrate the good things in life, and author of Life Begins at the End of Your Comfort Zone.

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Man in discussion with wife at dinner partyThomas Barwick/Getty Images

Conversation starter: Be brutally honest

“I find that being honest and cutting to the chase is best as it doesn’t waste anyone’s time. This may sound too bold but it’s worked great for me over the years. ‘Hi, my name is Alan and I have to let you know upfront that I have absolutely no interest in being added to your stable of purely platonic male friends in the near future. For me, it’s romance, sex, or nothing.'” —Alan Roger Currie, author of Mode One: Let the Women Know What You’re Really Thinking. Here are some simple ways to include communication in your romantic relationship.

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Mid adult business colleagues using mobile phone at creative officeMaskot/Getty Images

Conversation starter: Tell them their celebrity doppelganger

“I tell my clients to think about a celebrity that the person resembles then approach the person and say, ‘Did anyone ever tell you that you look just like Sophia Vergara?’ This approach is always effective because it seems genuine, and the person on the receiving end will blush, lighten-up and say thank you. Because you will now have shifted that person’s energy to one that illuminating and positive, it will act as a great lead-in to the rest of the conversation.” —Tom Kersting, co-host of A&E’s Surviving Marriage and author of Disconnected: How to Reconnect Our Digitally Distracted Kids

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Conversation starter: ‘Cheers’ them

“If you are in a bar and looking for an excuse to talk to someone, just go up and raise your glass and say ‘cheers!’ This is effective because it’s non-threatening, polite, and will most likely be reciprocated.” —Laura Bilotta, matchmaker and founder of Single in the City. Here are some simple ways to make new friends as an adult.

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Smiling shopkeeper helping client shop in clothing boutiqueThomas Barwick/Getty Images

Conversation starter: Size them up

“People love to be seen as useful and if you ask someone interesting for advice, you’ve got an instant conversation starter to boot. For instance, if you’re shopping ask them what they think of a color or a fit because the person you’re buying for is about their size or you want a man’s or woman’s opinion.” —April Masini, relationship and etiquette expert and author of the Ask April advice column

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Ride SharingLPETTET/Getty Images

Conversation starter: Ask to share their Uber

“With the advent of ride-sharing services, it’s become easier to get from one destination to another so if you spot someone interesting on their phone trying to hail an Uber or Lyft, offer to share a ride if you’re heading the same general direction. Sure, it might take a little longer to reach your destination but it’s a great way to have a conversation. At the very least, you’ll both save on the cost of getting to your destination.” —Brandon Wade, relationship expert and CEO of several dating sites

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Conversation starter: Plan a dream vacation

“Ask someone ‘If you got a free ticket to anywhere in the world tomorrow, where would it be?’ This line works for both in-person and online conversations. There isn’t anyone on this planet that wouldn’t take a free ticket and it’s a great way to learn about them. Are they adventurous? Would they rather stay in the country? Follow up with ‘What else is on your bucket list? and share travel stories.” —Marcie Rogo, co-founder of Or try out these best pick-up lines for women.

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Conversation starter: Scare them (just a little)

“One of my favorite conversation starters is asking ‘What was your high school mascot?’ It immediately takes the person back to their childhood and may lead to them sharing other information about the number of high schools they attended. Then I follow up by joking, ‘You know that you just gave me the answer to one of your online security questions, right?’ People usually laugh because it’s true, often launching into a conversation about other common security questions, online identity theft, mistaken identity or some other all-too-common modern woe.” —Jenny Korn, PhD, scholar of identity at the University of Illinois at Chicago

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Cheerful senior couple tourist standing by lake in nature on holiday, using smartphone.Halfpoint Images/Getty Images

Conversation starter: Ask them about their pets

If you’ve had any interaction with a dedicated pet parent, ever, you know that this conversation starter is an instant winner. Get ready for even complete strangers to regale you with stories of their furry friend or even show you photos and videos. And even if they don’t currently have a pet, talking about a pet they had growing up or a pet that they’re planning to have in the future will spark good conversation.

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Businessman Impressed With Colleagues IdeasHinterhaus Productions/Getty Images

Conversation starter: Repeat what they said

“If you are shy and don’t know what to say try being an empathetic listener. Reflect back what you hear the other person saying and offer compassion. This allows the other person to feel heard, validated, and accepted—and they’ll want to spend more time talking with you.” —Fran Walfish, PhD, Beverly Hills family and relationship psychotherapist, author of The Self-Aware Parent. These are the things good listeners do during every conversation.

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Smiling man talking with friends at dinner partyThomas Barwick/Getty Images

Conversation starter: Join the fun

“Introduce yourself by going up and saying ‘You look like you’re having a lot of fun so I wanted to come and say Hi!’ This is effective because it exudes confidence and charisma. Just make sure to pair it with a bright smile and make eye contact.” —Michael Banovac, founder of The Millionaire Date Doctor. 

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Businessman and woman using mobile phones while sitting on couch during conferenceMaskot/Getty Images

Conversation starter: Dig for little-known info

“Ask someone ‘What is something I would have never guess about you?’ This is a good starter because everyone likes to feel unique and their answer will reveal a little more than they might have initially been willing to give away. It’s a little intimate but not too much.” —Rochelle Peachey, dating and relationship expert and founder of I Love Your Accent

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Conversation starter: Use strategic sarcasm

“Solid gold opening lines get people to talk without being too serious while still getting the person to feel some emotion. A little sarcasm can help lighten the mood and make you feel relatable. My favorite examples: ‘Oh, I just love waiting in lines. Once I get to the front I just drink my drink as fast as I can so I can line up again.’ Or, in a bookstore, asking ‘Do you know how to read? I’m really struggling right now.’ Or if someone is on their phone say, ‘You must be smart, I only text with emoticons.'” —Harvey Hooke, author and human dynamics coach. Check out these underrated benefits of being sarcastic.

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Conversation starter: Ask about a mutual friend

“Mutual friends are good conversation starters when you are at a family gathering, party or any event where you were invited by the same person. Asking ‘So how do you know Mike?’ helps them share old stories and allows the two of you to jump right in and get to know each other. This one is especially effective if you let the mutual friend know you’re interested in talking to the person who’s caught your attention, so that they can slip in the conversation later on.” —Lori Bizzoco, relationship expert and founder of

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Conversation starter: Be pleasant

“It’s a simple social truth: Being happy makes others more interested in being around you. Try starting a conversation by expressing a pleasant emotion, like pointing out what a beautiful night it is. You should never try to shock someone into a conversation as it suggests you are scary, not interesting.” —Nikky Prause, a neuroscientist and licensed psychologist at the University of California, Los Angeles. Check out the daily habits of naturally polite people.

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Conversation starter: Comment on the venue

“Environmental small talk is appropriate for all events as it offers others the opportunity to engage or withdraw according to their comfort level. Try something like ‘I love the high ceilings in here’ or ‘What beautiful decorations, they’ve done an amazing job.’ Follow their lead and don’t be afraid to keep a conversation brief if you’re not receiving signals that they want to further engage.” —Jessica O’Reilly, PhD

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A woman speaking to another woman while smiling

Conversation starter: Say it with a smile

“It is viscerally impossible not to like someone who genuinely smiles at you. This means smiling with your entire face, including your eyes. Try this as you greet friends and colleagues and observe their reaction. A smile will disarm defenses, boost your likeability, and increase the chances of a positive conversation before you say a word.” —Wendy Patrick, JD, PhD, behavioral expert and attorney. Here are 52 little compliments that’ll make your friends and family smile.

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Two happy relaxed women sitting on couch at homeWestend61/Getty Images

Conversation starter: Find out what makes them laugh

Ask someone about the last funny video they watched, or just the last thing that made them laugh, like really laugh, in general. Whether it’s utterly silly or makes you burst out laughing as well, it’s sure to spark a conversation—and give you and your conversation-mate insight into one another’s sense of humor. Watch out for these 8 signs you’re a conversational narcissist.

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Senior Chinese lady having conversation with Malay friend outdoorsJimmyFam/Getty Images

Conversation starter: Ask them to describe themselves

Those cheesy icebreakers are cheesy icebreakers for a reason. Ask the old “describe yourself in three words” question and see what they have to say! Getting asked a question like that in a non–work orientation environment will surely pleasantly surprise them, and might even incite a more genuine answer. Familiarize yourself with the daily habits of naturally charming people.


Charlotte Hilton Andersen
Charlotte Hilton Andersen, BS, MS, has been covering health, fitness, parenting, and culture for many major outlets, both in print and online, for 15 years. She's the author of two books, co-host of the Self Help Obsession podcast, and also does freelance editing and ghostwriting. She has appeared in television news segments for CBS, FOX, and NBC.