#1 What is your most embarrassing moment? This is a go-to and a classic for a reason. No one’s answer will ever be the same. Plus, this lets you know how seriously this person takes themselves and if they can laugh at their formerly embarrassing moments.
#2 Do you have any weird talents or skills? This is always an interesting one. For example, I can lick my elbow and it is supposed to be impossible. That is something people always find super intriguing. But expect for them to ask the same question back, so if you aren’t prepared to walk on your hands or pop your shoulder out of its socket in the middle of a restaurant you can skip this one.
#3 What was your favorite childhood TV show? This always starts a fun and nostalgic conversation. You can reminisce on childhood and discuss how your sense of humor has changed, or if you would still watch that show today.
#4 What was your favorite Halloween costume as a kid? If you have a photo of yours on your phone that is a plus. Everyone loves to hear the answer to this question. Not everyone stuck with a witch or a ghost, so seeing what this person loved so much that they wanted to dress up as it is pretty darn interesting. Mine was a pumpkin princess… don’t ask.
#5 What was your worst fashion or style faux pas? Again you get to make fun of yourselves and each other. Talking about that mohawk you had, those frosted tips, or feathered hair is always enjoyable. Plus, it gets you the perfect segue for a compliment… “Well, you sure did grow up nicely.”
#6 What is the most cringe-inducing pick up line you have ever heard? Personally I love these. I mean not to actually be picked up with, but hearing such unbelievably bad or corny pick up lines is hilarious. Plus, knowing that someone actually thought it would work makes it impossible not to laugh.
#7 What products have you purchased from an infomercial? Infomercials are infamous for some really insane products. Some are meant for people who can’t make eggs, others for people who don’t own a blanket or robe, and some are just totally useless. Finding out what this person was intrigued enough to order will let you know a lot about them. And if the product was a bust as they usually are, this funny question can lead to a good story.
#8 If you could merge animals together which two would you choose and why? This can be a little weird to ask, but if you are both animal lovers it would be so interesting to hear their answer and their explanation behind it.
#9 What is the best dad joke you know? This is a funny and lighthearted, even corny topic. Everyone loves a good dad joke. I mean, how could you not?
#10 Which animal do you think would be the funniest if it could talk? This is great. Yes, we would all love our dogs or cats to be able to talk back to us, but hearing what a whale, ostrich, or giraffe has to say would be quite interesting.
#11 What is your guilty pleasure? This can be a great way to get to know another side to someone. This person may be all business or super professional, but finding out they love to watch The Bachelor or The Real Housewives would be shocking and hilarious.
#12 What is the most useless super power you can think of? Everyone always asks what super power you would want to have. Yes, that is a good question, but to make it funnier, ask this. There are some super heroes and sidekicks that just don’t make sense. Talking about the hypothetical situations where these powers would come into play can lead to a unique and creative chat.
#13 If you could be the opposite gender for a day what is the first thing you would do? Again this says a lot about someone. If you ask a guy and he says stare at himself naked, you know he may be a little superficial. So, this one, although funny, can also be pretty darn eye opening.
#14 What song is currently downloaded on your phone that you would be embarrassed if it started playing out of the blue? This is one of those funny get to know you questions that not only gets you a peek inside this person’s music taste, but also their actual music taste. Everyone is all about sharing their love for Drake, but when you admit to loving Nickelback or One Direction it opens up a whole new door.
#15 What is your least favorite word? Moist *sorry* is a popular one, but this is always pretty funny to learn about. Just keep this conversation in a location away from food.
#16 What is the worst/funniest thing you have ever seen while people watching? People watching is probably one of the most fun and interesting activities you can do. Whether you were eating lunch on a park bench or getting a tan at the beach, it is very likely you’ve seen some hilarious human behavior.
#17 What word can you never remember how to spell? You might not think about this very often, but we all have those one or two words that we can never spell right. For instance, mine are nauseous and guarantee. But yours might be restaurant, separate, or even vacuum. *I literally spelled vacuum wrong as I just typed it*.
#18 How do you think your last boss would describe you? This can be funny, embarrassing, or boastful. It can also tell you a lot about this person. If they think their boss would have nothing but wonderful things to say, they may be a little disillusioned. But everyone has something they did at work to pass the time *other than work*, if they share this they are pretty genuine.
#19 Have you ever had a weird interaction with a celebrity? Nearly everyone has met at least one celebrity. Whether it was at a book signing, on a plane, or just on the street, they are almost never normal. Whether the celebrity was rude, you were fangirling hard, or you mistook someone for someone else this is always a fun story.
#20 Would you rather be really hairy or completely bald? I had to throw at least one would you rather in here. But maybe skip this funny get to know you question if your date is in fact bald. Otherwise it is pretty funny to see what someone says.