300 Amazing Conversation Starters (Rejection Proof) post image

300 Amazing Conversation Starters (Rejection Proof)

The art of conversation seems to be mostly lost these days, but that doesn’t mean it has lost any importance! Knowing how to start and carry a conversation is something that will help you in all areas of your life.

When you are able to have conversations and start off strong, you capture a person’s interest. Whether it’s a potential lover, friend, potential employer, or random stranger off the street, your first impression will always matter,

MORE: Amazing Questions to Ask a Guy 

Having a great conversation these days is becoming increasingly rare. Blame Tinder, blame social media, blame whatever you want to blame—this is our reality. But it gives you an opportunity to stand out from the crowd when you can be truly “present” in a conversation. That’s the only way to win people over and really capture their interest and intrigue.

So let’s talk about the best ways to start a conversation.

Being confident is key to a conversation starter.

I actually have two keys you have to know if you want to be fully comfortable breaking the ice, striking up a random conversation with anyone in any situation, and always know exactly how to make an amazing first impression no matter what.

We’ll get to that at the end of the article, but first I want to arm you with my ultimate list of conversation starters. I’ve divided them into categories to make your life easier, but there is a lot of overlap and these questions can work across multiple settings. Pop culture questions are safe for almost anyone. Icebreakers are designed for strangers or people you don’t really speak to ever but want to strike up a conversation with. Then, you have questions to initiate conversations with your boyfriend and much more.

Bonus: I’m giving you “golden phrases” for each category to give you a mental formula of exactly what to say and apply in any situation, so you will not only have specific questions but a specific way to think about each category.

MORE: 230 Effective Questions to Get to Know Someone 

Here Are The Categories of Conversation Starters You Will Receive:

  • Entertainment/Pop Culture Conversation Starters: (what is your favorite/do you like…)
  • Icebreaker Conversation Starters: (do you enjoy…)
  • Conversation Starters About Apparel (Clothes, Shoes, Accessories, etc.)
  • Conversation Starters About Preferences: (vegan, food, iPhone or Android, creative or linear)
  • Conversation Starters About Traditions: (holiday celebrations, family traditions)
  • Conversation Starters for Your Boyfriend (how to have “talk,” get to know him better, how to start conversation)
  • Really Random Conversation Starters (preface with, “I know this is random, but…”)
  • Conversation Starters for Someone You’re Attracted To
  • Strange Conversation Starters: (would you rather…)
  • Conversation Starters About the Future: (where do you see yourself in X # of years…)

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Entertainment/Pop Culture Conversation Starters:

  • Who is your favorite politician?
  • Do you think the Internet is ruining our society?
  • Who is your favorite artist?
  • What is your favorite “creative” activity?
  • Do you get offended easily?
  • What offends you the most?
  • Are you creative?
  • Do you enjoy politics or not really?
  • What is the weirdest movie you have ever seen?
  • What is the one movie you can watch over and over again?
  • What is your all-time favorite song?
  • What is the last movie that made you cry?
  • Has a song ever made you cry?
  • Do songs change your mood?
  • What is your all-time favorite TV series?
  • Who is your favorite TV character?
  • What is the most random show you watch?
  • Do you like reality TV shows?
  • Who is your favorite reality TV star?
  • What was the most bizarre movie you’ve ever seen?
  • Do you enjoy going to movies, or do you prefer watching them at home?
  • How often do you exercise?
  • Do you enjoy going out?
  • Do you enjoy spending time with family?
  • How often do you watch sports?
  • Which do you prefer: Netflix or Hulu?
  • Is cable dead?
  • What was your 
favorite movie as a kid?
  • What was/is your all-time favorite Disney movie?
  • What was your favorite album ever?
  • Favorite musician?
  • Do you like dance music?
  • Worst music trend?
  • Is the music industry dead?
  • Do you think movies are better now or 20 years ago?
  • Is Titanic a good movie?
  • Be honest.
Have you ever watched a show but been too embarrassed to tell anyone about it?
  • Do you think people ever watch shows or pretend to watch them to fit in?
  • Have you seen the Notebook? If so, do you think it has helped or hurt the world? Just kidding—I think romantic comedies are… insert your opinion on them.
  • What is your favorite romantic movie if you have any?
  • Do you like any specific actors?
  • Is Leonardo Dicaprio over-rated?
  • Do you think Robert Pattinson was a good vampire?
  • Do you think the Oscars are rigged?
  • Is Hollywood a corrupt world?
  • Do you think Hollywood is full of rapists and deviants?
  • Do you think it is fair for Hollywood to pay actors so much?
  • If you could trade lives with one movie character, who would it be?
  • Who is your ultimate movie dream girl?
  • Who is the greatest actor of all time?
  • What is the funniest show on TV?
  • Do you like to binge watch shows, or ration out the episodes?
  • Which canceled show would you bring back?
  • Do you watch the news?
  • What is the most underrated TV show?
  • What was the first concert you ever went to?
  • What is the most annoying song of all time?
  • What is your favorite movie soundtrack?
  • What is your favorite music genre?
  • What is the best concert you’ve ever been to?
  • What was the last book you read that you couldn’t put down?
  • What was a book you had to stop reading because it was so terrible?
  • What cultural phenomenon have you completely not been interested in?
  • Have you ever walked out of a movie because it was so bad?

MORE: 20 Questions to Ask a Guy To Get Closer

Icebreaker (Just Met) Conversation Starters:

Golden phrase:“Do you enjoy…”

Don’t ask or assume anything; politics and religion don’t exactly make good conversation starters when you know nothing about someone. If you have context and have done some nice social media stalking, you might know more about them than you would ever like to admit, and can therefore just pretend you know nothing but ask questions that do align with who they are. I am not saying be fake, but simply don’t offend and let the conversation flow!

  • Do you enjoy meeting new people?
  • Do you enjoy your job?
  • What do you do for a living?
  • How long have you worked at this job?
  • Do you enjoy yourself even if you are around people you don’t like?
  • What is your family like?
  • Do you have a big family?
  • How often do you talk to your family?
  • Do you have any crazy siblings or family members?
  • Do you have any interesting relatives?
  • Did you go to college? If so, which one?
  • Where are you from? (Follow up: Did you enjoy growing up there?)
  • Do you enjoy relaxing or do you always need to be doing something?
  • What do you do when you need to relax?
  • Do you enjoy being spontaneous?
  • Do you enjoy being drunk?
  • Do you smoke?
  • Do you like discovering new bands?
  • Do you care about song lyrics?
  • Do you enjoy watching movies on your laptop?
  • Do you enjoy having free time or do you enjoy being busy?
  • Do you enjoy adrenaline rushes? So things like skydiving?
  • Do you enjoy cooking?
  • Do you enjoy baking?
  • Do you enjoy being asked about your life?
  • Do you believe in astrology?
  • Do you enjoy talking to random people you don’t know?
  • Do you enjoy flirting or are you shy?
  • Do you enjoy being constantly social or do you need time alone?
  • Do you enjoy being asked questions?
  • Do you enjoy being alone?
  • Do you enjoy having lots of friends?
  • Do you enjoy major blockbusters?
  • Do you enjoy big cities?
  • Do you enjoy biking or rollerblading more?
  • Do you enjoy movies or songs more?
  • Do you enjoy romantic or funny movies?
  • Do you enjoy movies without any famous actors?
  • Do you enjoy Indie movies?
  • Do you like experimental films?
  • How often do you watch a new movie?
  • Do you like classic films?
  • Do you enjoy going on vacation?
  • What is the best place you have visited on vacation?
  • Do you like comedians?
  • Who is your comedian?
  • Weirdest thing you have ever done?
  • What is the one place you’re dying to see?
  • What would you be doing if money wasn’t an issue?
  • What determines success? Hard work or luck?
  • What is something that makes you nervous even though it’s no big deal?
  • What is your favorite season?

MORE: How to Never Run Out of Things to Say On a Date

Conversation Starters About Apparel (Clothes, Shoes, Accessories, etc.):

  • Your golden phrases: What’s your favorite…
  • Do you like X or Y better?
  • What is your favorite kind of shoes?
  • Do you think uggs are ugly?
  • What is your go-to outfit?
  • For a guy: What is your favorite outfit on a woman?
  • What is your favorite kind of jewelry?
  • Favorite kind of accessories?
  • Do you like any kind of particular outfit on the opposite sex?
  • How often do you think about what you wear?
  • Does it take you a long time to get dressed?
  • Do you do your hair in the morning?
  • Do you spend a lot of money on clothes?
  • Do you go thrift store shopping ever?
  • Do you follow fashion trends?
  • Do you think buying clothes is fun?
  • Do you like spending time choosing outfits?
  • How long does it take you to decide what to buy?
  • Do you like online shopping?
  • What’s your favorite online shopping?
  • What do you think about men and beards? Yay or nay?
  • What is one item that’s been in your closet forever that you just can’t get rid of?
  • Do you enjoy cleaning out your closet, or are you a hoarder?
  • What are your go-to pajamas?
  • Do you think girls dress up to impress guys, or to impress other women?
  • What would you wear to work if you could wear whatever you wanted with no judgments?

MORE: The Best Would You Rather Questions

Preference Conversation Starters:

Your golden phrases: I am curious… do you like … Do you ever … How often do you …

  • Do you like cooking at home or going out?
  • What is your kind of environment to do work in?
  • How do you like to relieve stress?
  • Do you like relaxing alone or with others?
  • Do you want to be loved by many, but superficially, or loved by few for who you truly are?
  • Do you like being in relationships or are you more comfortable being alone?
  • Do you like being creative or do you like linear thinking?
  • Do you enjoy grocery shopping or is it boring?
  • Do you like eating healthy?
  • Do you ever diet/count calories?
  • Do you thrive in chaos or do you need complete order to feel safe?
  • What’s your weirdest habit?
  • Do you have any odd OCD traits that would be surprising?
  • Do you use an iPhone or Android?
  • Do you think you are good with technology?
  • Do you think technology is ruining us or saving us?
  • Have you ever been vegan? If so, do you think it’s weird to have only vegan food forever or would you enjoy it?
  • Do you think it’s wrong to eat meat?
  • Do you think organic meat matters or is it a hoax?
  • Do you shower in the morning or at night?
  • Are you a morning or night person?
  • Do you enjoy long walks or runs?
  • Are you an animal person? If so, what is your favorite animal?
  • Do you prefer apples or oranges?
  • Do you prefer meat or poultry?
  • Do you prefer steak medium rare or well done?
  • Do you prefer turkey burgers or hamburgers?
  • Do you like to plan or go with the flow?
  • Would you rather have an amazing house or awesome car?
  • What is your biggest guilty pleasure?
  • Describe your perfect day.

MORE: 425 Never Have I Ever Questions 

Conversation Starters About Traditions:

  • Asking about family traditions and holidays is an obvious way to connect with someone and learn more about them.
  • Does your family celebrate religious holidays?
  • What was your favorite family tradition as a kid?
  • Do you have any random family traditions that would be surprising to most people?
  • How often do you see your family?
  • Does your family act overprotective or did they let you go without needing to harass you a lot?
  • Do you celebrate Halloween?
  • Do you dress up for Halloween?
  • Do you see your family a lot?
  • Do you live near your family?
  • How often do you talk to your parents?
  • Do you have a good relationship with your parents?
  • Do you enjoy the holiday season or find it stressful?
  • Did you believe in Santa as a child?
  • Do you ever pray at a religious institution? (Church, synagogue, etc.)
  • Are you a spiritual person?
  • Which season has the best holidays and why?
  • What is your favorite holiday food?
  • What was your all-time favorite Halloween costume?
  • What was your most regrettable Halloween costume?
  • Is Valentine’s Day romantic, or just a gimmick?
  • If you could invent your own holiday, what would it be?
  • If you could get rid of one holiday, which would it be?
  • Do you know how to make any classic holiday food?
  • What is the best holiday dessert?
  • What is the worst holiday gift you’ve ever received?
  • Have you ever re-gifted something you got for the holidays?
  • What is your favorite holiday memory?
  • Which holiday is the most important to your family?

MORE: Crazy Truth or Dare Questions to Ask Your Friends

Conversation Starters for Your Boyfriend:

  • How have things been going at work lately?
  • Hey! How come you look so cute today?
  • What is your favorite part about our relationship?
  • In what ways do you think we could make our relationship stronger?
  • What is the best thing that happened to you today?
  • What is the best thing that happened to you this year?
  • What always makes you happy?
  • Why do you think people cheat?
  • What is your prized possession?
  • What is your dream vacation?

Outrageous Conversation Starters:

Your golden phrases: I realize this is crazy, but… I realize how insane this sounds, but…

  • Do you think aliens exist?
  • Are we all going to die one day and not know we existed?
  • Have you ever been in a food fight?
  • Do you enjoy food porn?
  • What is your favorite food porn?
  • If you could throw yourself in any situation, what situation would you pick?
  • Would you ever go to war?
  • Do you think war is government sanctioned murder?
  • Does money rule the world?
  • Does evil exist?
  • Do you believe in love?
  • Do you think fairies are cute?
  • Tell me something deranged about you. I don’t judge.
  • What is your biggest fear?
  • Do you have any truly weird phobias?
  • Come on, tell me a weird story about yourself. I really enjoy crazy stories! Trust me, you cannot shock me. I actually love being shocked if you can.
  • Don’t you think life is hilarious?
  • How often do you think about death?
  • Have you ever been to jail?
  • If you could go back and re-do one year of your life, would you?
  • What superpower do you wish you had?
  • What is your own personal version of hell?

MORE: Amazing Conversation Starters

Random Conversation Starters:

Your golden phrase: I know this is random, but…

Saying something is random opens the door for me to say off the wall things that would otherwise make someone slightly uncomfortable or confused. The word “Random” stops any weirdness and lets the conversation flow.

  • What is a weird or random talent that you have?
  • What keeps you up at night?
  • What is the weirdest dream you’ve ever had?
  • What is your biggest pet peeve?
  • What is something that drives you crazy even though most people don’t seem to mind?
  • Do you believe in any conspiracies?
  • What is your go-to midnight snack?
  • What technological discovery changed the world the most?
  • Do you actually like your job?
  • Do you really like that person? (insert person you suspect they do not like)
  • Do you believe in one night stands?
  • Do you think aliens exist?
  • Do you think it’s disturbing how people are always looking at their phones?
  • Do you think it’s interesting how obsessed society is with social media?
  • Do you think plastic surgery is cheating?
  • Have you ever cheated?
  • Have you ever thrown yourself at someone and been rejected?
  • Do you find our society today to be better or worse than the pre-technologically saturated world?

MORE: 50 Great Questions To Ask A Guy

Conversation Starters for Someone You Are Attracted To:

Your golden phrases:

So you might think this is strange… but

So you might think this is kind of forward… but

  • So you might think this is strange… but you are really turning me on right now
  • So you might think this is strange… but you look so hot right now I can’t focus
  • So you might think this is strange… but I can’t stop thinking about what it would be like if we… you know…
  • So you might think this is strange… but your smile makes me nuts
  • So you might think this is strange… but omg just stop looking at me like that, you’re making it hard for me to think (hide face, look down and giggle)
  • So you might think this is kind of forward… but I really really really feel … I don’t know… nevermind. (the word nevermind will be game-changing, tease him but also save you from having to be too crass and feel uncomfortable).
  • Do you think not having sex for a while is a good idea?
  • Have you ever been in a food fight?
  • Do you feel comfortable naked?
  • Is cursing attractive or unattractive?
  • What is the best place to go on a date?
  • What is the sexiest thing a woman can have on?

MORE: Conversation Starters That Make You More Interesting

Strange Conversation Starters:

Golden phrase: Would you rather… (this sets up the stage for you to say something truly off the wall and odd!)

  • If you could be on a different planet tomorrow, which planet would you choose?
  • Do you think when you die your soul dies too?
  • If you were going to die tomorrow, what would you do today?
  • If you could be a superhero which one would you be?
  • If you had to get stuck in a video game, which one would you choose?
  • Would you rather be a famous actor or politician?
  • Would you rather throw up or have a severe stomach ache?
  • Would you rather be fully heartbroken and ruined for life or never love?
  • Would you rather die young and happy or old and depressed?
  • Would you rather be a drug addict or a murderer?
  • Would you rather be able to fast forward or rewind time?
  • Would you rather be able to fly or breathe underwater?
  • Would you rather have the ability to teleport or read minds?

MORE: Best Tinder Conversation Starters to Get a Response 

Conversation Starters About the Future:

Golden phrase: What is your goal/dream/where would you want to be/where do you see yourself… in X amount of time?

Just present the question as… what do you want to accomplish or do or be in 5 years… 2 years.. 2 months…the point is to ask a hypothetical about some future time, who the person wants to be, what they want out of life—you will see what their true goals are and see how yours align.

  • What are your top priorities in life?
  • What is your life passion?
  • Where do you see yourself in 5 years?
  • Where do you see yourself in 10 years?
  • Where do you see yourself in 1 year?
  • Do you enjoy your current job?
  • What is your dream profession?
  • Do you think you can change the world?
  • If you could leave behind 1 thing on this planet what would that legacy be?
  • How often do you plan your future?
  • Would you like to be able to predict the future, or do you like not knowing what’s going to happen next?
  • What will the iPhone look like in a decade?
  • Do you want to retire eventually?

Important Things to Keep In Mind

You now have more than enough questions to suit any situation but I can’t just end here without explaining the two keys I promised at the beginning. Don’t worry—I did not forget.

Key #1: Be Prepared for Their Response to Be Unfulfilling

If you go into a conversation with any expectation of what you want the other person to say to you, this kills the vibe of your conversation from the beginning.

My biggest “trick,” if you want to call it a trick, is to truly not care about the outcome. I go into conversations expecting nothing and find that my genuine curiosity about others gives off a vibe that lets them feel comfortable. I’m not there to extract a response. I am simply ok with the fact that they might not reply, they might reply with a cold, half-response and brush me off as if I am irrelevant (note: people do this out of either their own insecurities, trying to “be perceived as indifferent” and as if they do not care which is in their minds cool), or they might just not be interested in what I have to say—does this bug me? no!!!

If you care about how someone replies to you, you miss the heart of what having a conversation means: mutual benefit.

Focus on seeing whether your conversation is rewarding mutually—not for just you and not for just the other person. If you align, great—if not, that is fine too! No one is bad, boring or uninteresting. You simply did not find a conversational match and that is fine.

Just make small talk, ask “typical” questions, and move on. Don’t try to “force things” to happen.

As I said, it all ties back to not caring about how the person responds. Having no set idea of how you want them to reply but simply letting the conversation happen and accepting that they could be vicious, rude, and ignore you and it would not impact your self-worth in any way.

MORE: 32 Conversation Starters That Don’t Involve The Weather 

Don’t Try To Impress Ever

It boils down to not trying to impress and not being ashamed of your words—be clear and comfortable and never try to impress. The vibe you give off when trying to impress comes off as insecure and people read this on an instinctual level. It makes them not want to have a conversation with you because trying to impress is a desperate mindset.

But what if you want to impress someone? Sometimes you do want to make a good impression and that’s fine. I’m not saying don’t ever care what someone thinks, I’m saying don’t get lost in the idea of impressing because it just sabotages you.

And if you have to be professional, prepare! Have an idea of the person before you meet them. Be well informed. Research. Know facts. This is actually another way to automatically come off as comfortable—when you are comfortable you make people feel good around you and you can let go and relax and show your best self.

Key #2: Be Patient And Listen

Listening means you are able to be present because you don’t have the mindset of trying to impress (described above). You are comfortable and OK.

So listening is your superpower that will take your conversations to the next level.

Listening means observing the other person, truly hearing them and responding based on what they say. This is key—being present and being able to connect with their words and their facial expressions.

To sum up:

    • Listen and don’t interrupt
    • Don’t overshare: share approximately what the other person does
    • Always begin small and work your way up if you get to know someone better
    • Put “feelers” out there and never be ashamed of how someone replies to you
    • Be prepared and do research if you are in a professional situation
    • Never strike up a random conversation using a random line you do not feel comfortable with (this will backfire)
    • Be present and engage with the human in front of you
    • Never try to impress, just exist and don’t be too hard on yourself!


Looking for more questions? Well, you’re in luck, because we’ve got plenty!

Would you rather questions: these apply in “strange” conversations in particular because it sets up a strange, hilarious note for the conversation!

Truth or dare questions: these work because it again sets up the stage to ask inane questions.

Never have I ever: this game is both hilarious and highly revealing, and always a blast!

250+ Questions to ask a guy– This is the ultimate list of questions to ask a guy to get closer and really form a deep connection.

1 comment… add one

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Love these! Great ideas, I’m gonna print this out.

Reply March 4, 2018, 4:54 pm

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