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20 Really Good And Funny Conversation Starters

You see an interesting person sitting at the table across from you or maybe you’re out on a first date.  What you need right now are really good conversation starters and some of the best ones use a little humor.  A funny conversation starter can break the ice and allow you both to get to know each other as well as enjoy your time together.  Here are 20 good and funny ways to get your conversation started.


What is the worst thing you can say on a first date? This is a really good way to break the ice because you can find out what the other person expects on a first date.  Plus you might get to hear about one of their worst first dates and avoid all of those pitfalls.

If you could be any animal, what would you be? This can let you get a little glimpse into how the other person sees themselves.  Often people will choose an animal that has a few traits that they see in themselves.  And who doesn’t like animals?

What is the most random thing you have ever said? We all have moments of weirdness and it can be funny to find out that other people are just as random as us.  You might even find out that the other person has more in common with you than you think.

What is the silliest thing you’ve ever bought at the store? Stores like Target and Walmart have everything for everyone and that can lead to some funny purchases like toilet paper and peanut butter.  You can see what they shop for and can giggle at the random combinations you have both come up with over the years.

What was the best meal you’ve ever had? Food is a great way to see what another person is like.  It can give clues to their heritage, traditions, and tastes.  If you know what a person likes to eat you know a little bit more about their personality.

What was the last movie you saw that made you laugh out loud? This question lets you learn two things.  What the other person finds funny and what movies they enjoy watching.  They might actually start laughing as they tell the story which is a good way for them to get comfortable around you.

What is the weirdest birthday present you’ve ever gotten? You can figure out when their birthday is and you can learn what present NOT to get them.  It also can introduce you to some of their family members and what environment the other person grew up in.

What’s your biggest kitchen fail? Maybe they forgot the cookies in the oven or had a casserole that ended up more like a brick than a meal.  Now you know if they like to cook, what they like to make, and maybe what you shouldn’t have them prepare for you!

Have you ever sent a text message to the wrong person? It can be funny to look back at those, “Love you too” texts sent to bosses instead of parents.  We’ve all had an embarrassing moment due to our phones and sharing them makes it less mortifying and more fun.

Who is your oddest celebrity crush? Celebrities like Leonardo DiCaprio and Megan Fox usually get all the attention due to their good looks, but most of us have another celebrity crush that might not be in the mainstream.  This question lets you see who the other person likes and what some of their other interests might be.

What is the most embarrassing thing that happened to you in school? We all have a moment in school that we look back at and cringe.  Maybe you tripped in front of the class or called your teacher mom.  They might have made you want to crawl into a hole all those years ago, but now it’s something you can laugh at and share.

Which sitcom apartment would you want to live in? You can find out what TV shows they like to watch and their living style as well.  Maybe they like Monica and Rachel’s apartment from Friends or they have their eyes set on living in the White House like the Underwoods on House of Cards.

What is your guilty pleasure? Maybe you both like to sit in your sweatpants and eat cookie dough while watching 90’s TV shows.  You never know how much you might have in common with the other person until you learn their guiltiest pleasure.

What’s your favorite candle scent? Smells are closely tied to our memories and emotions.  The smell of apple pie might bring back memories of their grandma making holiday pies or the scent of pine make them think of a hike they took with their dad.  You can learn a lot about their likes and their memories with this question.

Who would you hate to be stuck on an elevator with? You can find out what they find annoying or unattractive in other people.  No one wants to be stuck in an elevator and adding in the extra fun of an annoying pest can bring out a different side of someone.

What would be your theme song? Music is a great way to break the ice because we all have our favorite artists and genres.  It can be fun to think about having our own theme song and who would sing it.  Find out if they would have different songs for different parts of their day too!

Which cartoon character would you pick to be your best friend? We all need a sidekick and a cartoon one can be way more fun than another human.  You can see what cartoons they like to watch and get a look into their more child-like personality with this question.

What has been your weirdest dream? This isn’t about weird dreams or goals, but weird dreams you have while you’re sleeping.  We’ve all woken up after a head scratcher and wondered what it meant.  Now you can hash it out and see who has the weirder sub-conscious.

What is your signature dance move? Maybe they’re creative and have made up their own or they fall back on standards like the side-to-side a la Hitch.  You can see if they like to dance as well as dance to the beat of their own drum.  Plus you can find out if they know how to do the cha-cha slide.

What color would you be willing to wear every day for the rest of your life? Yeah, it’s a silly way to find out what color they like but it can also let you see what they would be willing to do forever.  Who knows?  Maybe they would be happy wearing neon pink for all eternity.

It’s always good to make someone laugh.  It helps them open up and get comfortable and it can lead to some really interesting conversation.  Try any of these questions the next time you need to break the ice and see if you can get a giggle or two out of the other person.

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