300+ Best Conversation Starters for Any Situation

By Katee Fletcher Updated January 21, 2021

Trying to meet someone new in any capacity can be nerve-wracking and difficult. If it’s in a professional setting, then you’re questioning how to make yourself stand out as a candidate. If it’s a date, then you’re hoping the conversation flows easily, and the other person likes you. If it’s looking for a new friend, then you’re wondering how to connect with someone in a non-awkward way. Small talk is not easy sometimes, especially if you’re struggling to kick-off a genuine conversation. If you’re looking to meet someone new, be sure to read over this article to find conversation starters that work for you and tips to help you facilitate them!

Conversation Tips

Listen: If you want to be a good conversation partner, you need to make sure you’re also listening to what the other person is saying. Engage them in the conversation by asking follow-up questions or stemming a point off of what they mentioned. Listening will make the person you’re talking to feel heard and valued, boosting your chances of connecting!
Body Language: Another valuable part of conversation is the cues you send through your body language. Do the following things to show the person you’re talking to that you’re interested and actively listening:
- Keep good eye contact and turn your body towards them.
- Open your body to them by keeping your arms and legs uncrossed.
- Nod, say small reassurances like “yes,” or use other facial expressions to ensure the other person that you’re following what they’re saying and you’re engaged.
Compliment: Starting a conversation by commenting on someone’s shoes or nice shirt always helps to make someone instantly connect with you. No matter who it is, it gives the other person a quick boost of self-esteem and shows them that you’re observant and interested in interacting with them!
Find Common Interests: Starting a conversation by asking someone about themselves and what they enjoy is always valuable. Hearing about their hobbies or passions allows you to possibly connect over something in common! However, even if you find nothing in common, allowing the other person to talk about what they love is a great way to get them excited about the conversation and be more vulnerable.

Conversation Starters for a Professional Environment

Networking:

Connecting with people that work within your desired or determined career path is a great way to find new opportunities and learn something new about the industry. Look through the options below to find a good conversation starter that works for you and helps you connect with someone easily at any networking event!

What inspired you to start a career in this industry?
What motivates you throughout your workday?
Is there anything you would change about the industry if you could?
What kind of legacy do you want to leave behind during your career?
What do you believe the pinnacle of your career is?
Are there other aspirations outside of your job that you would like to achieve?
What do you think are the most valuable traits an employee can have?
What’s the most valuable piece of advice you’ve received while working in this industry?
What advice would you give to an employee who is just beginning their career?
What’s the most rewarding part of your job?
What has challenged you in this industry?
Is there anything you would change about your career path thus far?
How has this company impacted you and your life?
In what ways has this industry positively or negatively surprised you?
What’s the most beneficial thing you’ve learned while working at this company or in this industry?
What goals did you set for yourself along the way to reach the point you’re at now?
What are you most passionate about in life, and how does this align with your work?
Who is a role model you have in the industry?
What does success look like to you?
How much do you value work/life balance?

Asking for Feedback:

Having a conversation with your boss or supervisor about the work they’re assigning and how you’re executing it is very valuable. This shows your supervisor that you are willing to put in the effort to do your job correctly and that you’re willing to improve if needed. Look through the list below to find a good question to spark this necessary conversation topic!

How can I advance as an employee?
In what ways can I better facilitate the work I’m doing?
Is there anything I can do to improve the work I’m doing?
Is there anything you would like me to change about the work I’m submitting?
Could you provide me with some feedback on my work?
How can I improve my productivity?
Where do you see me with this company in 5 years?
What skills do you think could help me improve?
What have I been doing well thus far?
Which project has displayed my best work thus far?

Work Happy Hour:

Participating in the happy hours your work offers is a great way to get to know your colleagues in a different way. Take a happy hour as an opportunity to make a new friend, understand the company on a deeper level, and connect professionally but personally as well! Read through the list below to find a conversation starter to help you connect easily with a coworker!

What department do you work in?
What sparked your interest in working for this company?
What inspired you to do the work you do?
What about this job has impacted you the most?
How did your past jobs lead you here?
What kinds of projects have you been working on this year?
What’s the most influential project you’ve worked on while at the company?
What are your aspirations in life?
What makes you the most passionate, inside or outside of work?
Tell me about what your department does.
How long have you been working here?
Do you see yourself staying here for a long time?
What are your favorite aspects of this job?
What would you change about your work if you could?
What’s the coolest thing you’ve experienced while working here?
What’s your dream role in this company?
What was your first job?
What’s your favorite place around here to get lunch?
Are you from this area?
Do you see yourself living here forever?

Funny Conversation Starters for the Work Place:

How many emails have you put off this week?
What’s the weirdest company call you’ve made this week?
Hear any office gossip lately?
What lie have you told to get out of work?
Tell me about the craziest experience you’ve had while working here.

LinkedIn Messaging:

Finding opportunities and networking through LinkedIn has become increasingly popular in recent years. If you’re struggling with where to begin when messaging a connection, look over the conversation tips below!

Messaging Tips

Be Concise: Try not to write with too much flowery language. Instead, try to make your writing concise by stating who you are, why you’re writing, and thanking them for their time. This gets your point across more clearly and conveys a nice but professional attitude.
Use a Specific Title: If you’re messaging a connection, then you have the option of adding a title to your message. Make your title something eye-catching and specific, as this will be the first thing the other person sees when they see the message.
Personalize Your Message: Similar to in a cover letter, if you’re reaching out to a connection in search of a new opportunity, it’s great to connect with them over something in common or giving them insight as to why you’re truly interested.

Conversation Starters to Connect With Potential Friends or Love Interests

Conversation Starters About Favorites:

Asking questions about someone’s favorite things is a great way to brighten the mood and get them excited about the conversation. Try to ask some questions or branch off their answers to keep the conversation going after and avoid awkward silence. If you’re looking for a great ice breaker, be sure to read the list below to find your favorite conversation starter about favorites!

What color have you always loved?
What book could you not put down once you picked it up?
What movie always wins you over?
Who is your favorite actor?
Who is your favorite actress?
What TV show can you watch over and over again?
What candy do you always crave?
What’s your favorite food to eat when you’re sad?
What type of food could you not live without?
What meal would you have to eat before you die?
What board game always gets you excited?
What video game have you mastered?
Which family member do you like spending the most time with?
Which friend is like family to you?
What app do you love the most?
What drink do you always crave?
What flavor of ice cream is your go-to?
What dessert do you enjoy the most?
What band or artist did you plaster on your bedroom walls as a kid?
What band or artist do you most adore?
What song could you listen to on repeat?
What album could you not live without?
What instrument do you love to play?
What is your favorite part of the year; winter, spring, summer, or fall?
Which month is your favorite?
Do you have a favorite or lucky number? What is it?
Which day of the week makes you the happiest?
What time of day do you prefer?
What mealtime do you most enjoy?
What room in your house makes you the most comfortable?
Do you have a favorite cocktail? What is it?
What’s your favorite activity to do outside?
Where would you prefer to be, the beach or the mountains?
Where would you prefer to be, a city, a suburb, or the countryside?
Where is your favorite place to vacation?
What is your favorite place to travel to?
Where is your favorite place you’ve ever lived?
What subject did you love in school when you were a kid?
What quote do you live by and love?
What chore did you dislike the most as a kid?
What podcast do you love to listen to?
What is your favorite store to shop at?
What is your favorite aspect of where you grew up?
What is your favorite fast-food restaurant to eat at?
What is your favorite restaurant in this area?
What is your favorite pastime?
What is your favorite way to have your coffee?
What holiday do you love to celebrate?
What scent do you love?
What’s your favorite guilty pleasure snack?
What kind of pet do you prefer?
Do you prefer working on a Mac or PC device?
What kind of flower do you love to see?
What animal do you love?
Which genre of music could you listen to for the rest of your life?
What word do you love?
What kind of cereal could you not live without?
Do you prefer waffles or pancakes?
What genre of movie do you prefer to watch?
What celebrity do you adore?
Are you a night owl or an early bird?
What concert was the best you’ve ever been to?

Conversation Starters About Childhood:

Asking someone about their childhood and reflecting with them on their memories is a great way to connect with a potential friend or love interest intimately. This is a great topic for creating a meaningful conversation but be patient as this can also be a vulnerable area for some.

Who were you closest to as a child?
When you were little, what did you want to be when you grew up?
Would the younger version of yourself be proud of who you are today?
What is your favorite childhood memory?
Did you and your family have any traditions when you were a child?
Who was your role model as a child?
Who was your best friend in school growing up?
Were you a picky eater when you were little? What wouldn’t you eat?
Where did you live growing up?
A funny conversation starter could be: How old were you when you discovered Santa Claus wasn’t real?
What was your favorite toy growing up?
What did/do you call your grandparents? If it’s a unique name, why?
What did you fear when you were a child?
Which school year was your favorite when you were a child? Why?
Where was your favorite place to go when you were younger?
What candy were you addicted to when you were a kid?
What TV show did you love as a kid?
Did you have your own room growing up, or did you have to share?
What aspect of your childhood do you wish you still had?
What’s your earliest memory?

Conversation Starters for Texting and Social Media:

An easy and fun way to get to know someone today is through social media and text messaging. If you’re looking to date, there are plenty of dating apps like Tinder, Hinge, Bumble, Grindr, etc. If you’re looking to make friends, texting is an excellent way to develop social skills while still getting to know someone! The great thing about technology is that it gives you ample time to think about what you want to say or how you want to say it before you send it. Not to mention, social media apps like Instagram, Facebook, Twitter, etc., allows you to stay up to date with old friends and connect with them in new ways.

Casual Texts

We haven’t spoken in a while, what’s been going on in your life lately?
What was the best and worst thing that happened to you today?
Describe your mood in an emoji.
What’s your favorite emoji to use and why?
A fun way to get to know someone and kick-off a conversation is by saying: Let’s play 20 questions!
Have you been to any fun bars or restaurants lately? We should go together sometime!
Do you have any plans this weekend? We should hangout!
What’s your favorite cafe? We should go together sometime and get a cup of coffee.
Would you want to grab a drink after work sometime?
What shows have you been watching lately? I would love to check them out!

Flirty Texts to Spark Intimacy

You look like my next girlfriend/boyfriend.
You look like a fun time *eyes emoji*.
If you could pick anyone in the world to go on a date with, who is it, and why is it me?
You’re cute, but you would be cuter with me by your side.
Why hello there *heart eyes emoji*.
What’s your dream date, and when can I take you on it?
Describe your perfect weekend, but don’t forget to include me *winky face*.
I was hoping we would match.
Cute smile, what makes it come out the most?
A great conversation starter that’s also flirty is complimenting them on something in their profile like their outfit, nice muscles, cute dog, etc.

Conversation Starters to Reconnect With a Loved One

Deep Conversation Starters:

Asking questions on heavy topics is a great way to get to know someone’s deeper side and how they see the world. Using these deep conversation starters is a great way to start an interesting conversation with someone you care for but want to learn more about. Read on below to find a great question to ask your loved one!

What’s one thing you would change about our society if you could?
If you won a million dollars, what’s the first thing you would spend it on?
What’s been your favorite year of life so far, and why?
If you could have dinner with any three people in history or the present day, who would they be and why would you pick them?
Do you consider Pluto a planet?
What are the top five things on your bucket list?
What aspirations do you have for the rest of your life?
Do you feel you’ve achieved your goals in life?
Looking back on your life so far, what would you go back and change if you could?
Glass half full or glass half empty?
What came first, the chicken or the egg?
Do you believe in an afterlife?
Do you believe in a higher power? Tell me about that.
Which qualities make a good friend?
Which qualities make a good partner or spouse?
Which qualities make a good parent?
What’s your biggest fear in life, and why?
What’s your biggest regret?
How old were you when you had your first heartbreak?
Who was your first love?
What was your biggest failure?
Where do you see yourself in the next 10 years?
What obstacles are holding you back from working your dream job?
What in life is holding you back from reaching your full potential?
If you found out you are going to die tomorrow, what would you spend today doing?
Can money buy happiness?
How would your closest friends and family members describe you?
What’s your favorite thing about yourself?
What’s your least favorite thing about yourself?
What age do you feel inside?
If there was a fire burning your house down, what would you grab before running out?
If you could live one day of your life over again, which day would you choose?
What’s your next step in life?
What’s the most valuable piece of advice you ever received from your parents?
What cause do you feel strongly tied to and why?
Would you ever take a bullet for someone? If so, who is it, and why?
What would you change about this country if you could?
What travel destination is on your bucket list?
If you could live anywhere in the world, where would it be and why?
What goal do you think humanity is not focused enough on achieving?
Do you believe in Karma?
Do you believe in fate?
Do you believe in love at first sight?
Do you believe in free will?
What is the craziest thing you’ve ever done, and would you do it again?
When have you felt the proudest of yourself, and why?
What do you think makes a happy life?
If you could give back to someone in your life right now, who would it be, and what would you do?
Do you live spontaneously or have to plan things out?
What or who are you most afraid of losing?
If you could change one thing about how you were raised, what would it be?
If you could change one thing about your daily life, what would it be?
When do you think lying is okay to do?
Are you more like your mother or your father? How?
Is there a difference between loving someone and being in love with someone? Why or why not?
If you could create one law that everyone had to obey, what would it be?
What excites you most about the future?
If there was nothing to hold you back, what would you want to do every day?
If you could give a piece of advice to your younger self, what would it be?
How do you find peace and relieve your stress?
What’s the meaning of life?
Do you believe in monogamy?
What’s the greatest invention of the 20th century?
Do you think the legal drinking age should be lowered?
Should marijuana be legalized?
What would you rather have, more power or more money?
Are we molded by nature or nurture?
Is reality subjective?
What is a miracle that happens daily?
What does living life to the fullest look like to you?
Are emotions necessary for human survival?
What is the most beneficial emotion?
What’s the most destructive emotion?
What will most likely destroy the human race, and can we avoid it?
Are people obligated to help others or only themselves?
Are you named after anyone? If so, who?
If you could know the absolute and total truth to one question, what question would you ask?
If you could open up a business, what would you open, and what would you call it?
You can be beautiful, or you can be rich; which would you pick?
Has a wish you made ever came true?
If you could start a charity, what would it be for and why?
What’s your best trait?
Do you wish on stars, dandelions, candles, etc.? Why or why not?
What book has had the greatest impact on your life?
When was the last time you cried, and what was it over?

Funny Conversation Starters:

Whether it’s with someone new or someone you know, if you’re looking to lighten the mood, asking these funny conversation starters is a great idea! These are great to ask over the dinner table at home or at a dinner party event with friends to hear some funny stories and thoughts.

Tell me about the worst piece of advice you’ve ever acted on.
What’s the worst pickup line you’ve ever been told?
What’s the awkwardest pickup line you’ve ever used and failed with?
Tell me about the weirdest date you’ve ever been on.
Do you believe in any strange conspiracy theories? Tell me about them!
Do you believe in aliens? Why or why not?
If you could have one superpower, what would it be and why?
What’s your spirit animal, and why?
If your life was made into a movie, what would be the title?
Tell me about your worst job interview.
Did you ever have an imaginary friend? Describe them to me.
If you became the opposite gender for one day, what’s the first thing you would do?
If you could spend a week in another person’s shoes, whose life would you want to live?
If you were a condiment, which one would you be?
What TV show or movie can you quote an embarrassing amount of?
What’s the worst gift you’ve ever received but pretended to love when you opened it?
What’s the oddest thing you believed as a young person?
If you were deserted on an island, who would you want to be deserted with and why?
Which superhero would you love to be if you could?
Do you have any tattoos? If so, explain what they are; if not, what tattoo would you get if you had to?
Which Disney princess is your favorite?
If a genie gave you three wishes, what would they be for?
Tell me what your biggest pet peeve is.
If you had to be a fictional character, which one would you pick?
Do you have any secret talents? Give me a sneak peek!
What’s the funniest prank you’ve ever pulled on someone?
What’s the funniest prank someone has ever pulled on you?
Try to impress me with a good knock-knock joke.
What’s your signature dance move? Show me!
Would you travel to another planet if you could?
Which reality TV show would you apply to be on?
What’s the oddest nickname you’ve ever been given?
What food do you find absolutely inedible?
What’s the craziest lie you’ve ever told, and why did you tell it?
Do you prefer your toilet paper over or under?
Have you ever peed in a swimming pool?
If you could have an extra body part, what would it be?
If a tree falls and no one hears it… does it make a sound?
Tell me about the strangest dream you’ve ever had.
What is an irrational fear you have?
Why do you drive on a parkway and park in a driveway?
Why are they called apartments if they’re so close together?
If you could live in a storybook, which book would you pick?
Why does your nose run and your feet smell?
What was the best thing before sliced bread?
What’s the last thing that made you laugh so hard your stomach hurt?
Have you ever laughed so hard that you peed your pants? If so, what made you laugh?
Where is the strangest place you’ve ever traveled to, and what made it strange?
What’s something that’s popular right now but annoys you a ton?
What would you name your boat if you had one?
If you had to pick a body part to be without, which would it be and why?
If you had to rename yourself, which name would you pick?
What’s your middle name?
What is the least attractive quality a person can have?
What insect would you banish from Earth if you could?
What’s the weirdest thing you’ve seen someone do while operating a car?
What’s your favorite curse word to use?
What’s the cringiest trend you participated in as a kid?
Who’s the funniest person you’ve ever met?
How would you describe your humor?