If you want to be able to spark a conversation with absolutely anyone you meet, there is nothing better than humor. People love to laugh and tend to open up when they are presented with a funny question of some kind. Whether it is someone you are interested in dating or a new friend, these questions can help you get things going. They will also teach you some new things you never knew about the person, which can be a good thing for a number of reasons.

1. If you Could Build a House out of something Weird, what would it be?
This question leaves a lot of room for creativity and can definitely provoke a lot of hysterical laughing. Chances are the person has never even thought about this before, which makes it that much better. As strange as it sounds, their answer will probably give you some insight into them as a person.

2. What is the Strangest Habit of Yours?
We all have our weird little habits that are often times just as funny as they are strange. This question will give you the opportunity to learn about the other person’s habits, which should tell you something about them overall. Maybe it’s a habit they aren’t even fully aware of. It could be an eye-opening experience for both of you.

3. What is the Most Bizarre Dream You Have Ever Had?
Ask the person you are getting to know to describe the weirdest dream they have ever had. We usually don’t remember most of our dreams for very long, but some stand out more than others. It is very likely that they will be able to give you an answer to this question without much trouble. It is definitely something that can get both of you laughing pretty quickly.

4. What is Your Most Embarrassing Moment?
While this question is a bit personal, it also has the potential to really break the ice with someone you don’t know very well. A vast majority of people have a vivid recollection of their more embarrassing moments, so they should be able to recall the memory right away. It should give you both a good laugh. This is a particularly good question because it affords you the opportunity to learn something personal about them, which can help you form a stronger bond.

5. What Was Your “First Time” Like?
This is another fairly personal question, but it’s something that a lot of people are actually willing to talk about with people they don’t even know that well. Most people’s first time being intimate with another person is loaded with awkward humor.

6. What is the Worst Haircut You Have Ever Had?
Most people have a bad haircut story that they can share at a moment’s notice, and it’s usually pretty entertaining. Depending on just how bad the haircut was, you might be in for some gust-busting humor. Ask them to describe the haircut in detail and the circumstances surrounding it. It might have been a hair style they regret or a mistake on the part of the stylist, but there’s always a story to tell.

7. What is the Ugliest Thing You Have Ever Worn?
We all have regrets when it comes to the things we have worn in the past. The 90s was filled with all sorts of ugly outfits and weird trends, but every generation makes fashion mistakes. This is another great question because there are bound to be some funny stories.

8. What is the Strangest Tradition Your Family has?
Not everyone is going to have a super funny or entertaining story to tell for this question, but it’s still worth asking. Some people have pretty bizarre traditions in their family, and it could provoke an interesting conversation both ways.

9. What was your biggest Childhood Fail Moment?
Every person has a bunch of childhood fail stories that are usually pretty embarrassing but funny. It is very likely that the person you are talking to will have at least one good one to give you off the top of their head. You can reciprocate with your own story from your childhood, which should create a nice bonding moment between the two of you.

10. What Celebrity do you look like?
We have all been told by someone else which celebrities we look like at some point, and sometimes the answers can be pretty hilarious.

11. If You Had a Boat, What Would You Name it?
Boats are famous for having strange and usually funny names, so ask the person you are talking with what name they would come up with for theirs. This is another good question that promotes creativity and humor.

12. If You Could Switch Places With Anyone, Who Would it be?
Anyone who says they haven’t thought about switching places with another person would just be lying. The answer to this question is usually pretty interesting and gives you some insight into what they are like as a person (or what they want to be like).

13. What is Your Favorite Guilty Pleasure Song?
Ask the person what their favorite guilty pleasure song or band is. Most people have certain songs and artists they love but won’t freely admit to with most people. It might take some cajoling, but the answer will most likely be worth it.

14. What Disney Character Do You Most Identify With?
This is a pretty interesting question because it can be really funny while also showing you how the other person sees themselves. There are lots of these characters to choose from, so they should be able to think of at least one.

15. What is Your Funniest Talent?
You never know if the person you are speaking with has some hidden talent that just so happens to be funny. Maybe they can touch their nose with their tongue or lick their own elbow. There are so many possible answers to this question.


Anna Perkins is a relationship writer who offers her own forthright opinion over the worlds of dating, romance, relationships , marriage and friendships. She loves cats, traveling, spending time with her son and husband.

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