There are many different questions that you can ask someone you want to bond with, but some of them are better than others. Humor is always something that seems to bring people together, so it makes sense to ask funny questions. Once people start laughing together, something special happens between them. These 25 questions can help you get better acquainted with almost anyone that you want to form a deeper connection with. Some of them are a little personal, but that’s the whole point.

1. What Was Your First Job?
Ask the person what their first ever job was. Chances are it will be something interesting that they will be able to talk about a little bit. Maybe they will have a funny story to tell.

2. Have You Ever Met a Celebrity?
Not everyone has met someone famous, but it can definitely be funny and entertaining if they have. Who was the celebrity and what were the circumstances?

3. What is One of Your Most Embarrassing Moment?
When we embarrass ourselves in a really big way, it’s usually funny to some degree. This question is a good chance for the person to laugh at themselves while you learn something new about them.

4. What is the strangest food combination you enjoy?
A lot of people like some pretty weird food combinations, and you might just find something to bond over. Is it ice cream and pickles? If nothing else you will both probably get a good laugh from the answer.

5. Which Fashion Choice do You Regret Most?
Maybe it’s a really ugly sweater or a pair of neon cargo pants, but everyone has fashion regrets. Admitting such an embarrassing fact about themselves will more than likely bring the two of your closet together.

6. Have You Ever Bought Anything from an Infomercial?
There are all sorts of crazy and weird things that are sold on late night infomercials. Ask the person if they have ever actually called the number on the screen to buy one of these kinds of products.

7. What is one of Your Biggest Guilty Pleasures?
Whether it is a certain food, musical artist or something else, we all have our guilty pleasures. The answer to this question will teach you something new about them while establishing more of a personal connection.

8. If you could have one Useless Super Power, What Would it be?
There are all sorts of potential superpowers that are just absolutely useless. Pretty much anyone can come up with multiple funny answers to this question without thinking very hard.

9. If You Suddenly Woke up as the Opposite Gender, What would you do?
Ask the person what the first thing they would do is if they woke up as a man or woman. The answer to this question will probably surprise and make you laugh simultaneously.

10. What is Your Least Favorite Word?
When you ask someone what their least favorite word is, they usually have to think for a few seconds before coming up with a response. People usually have the strangest answers that are entertaining and hilarious.

11. Who is the strangest person you have ever worked with?
Most people have worked with some pretty odd people, and it can make for a gut-busting story. Maybe it’s a habit the person had or just the way they behaved while on the job.

12. What was Your Favorite Band 10 Years ago?
People’s musical tastes tend to change over time, and what the person likes now might not be what they liked a decade ago. They could give you a pretty funny answer.

13. What was the Worst Pet You Ever Had?
A lot of people have had pets that completely annoyed them to no end. The person you are talking to might have some good stories to tell you.

14. What is the Nerdiest Thing About You?
You could potentially discover that you have some things in common with the other person when asking this question. There is a little bit of nerd in all of us, and sometimes it takes asking someone to get to know that side of them.

15. What is the Worst Gift You Have Ever Received?
Ask the person to tell you about the worst or most inappropriate gift they have ever gotten from someone and just wait to start laughing with them.

16. What is the Funniest Mistake You Have Ever Made?
Sometimes the mistakes w make our just tragic, but other times they are absolutely hilarious. This question will be sure to bring you closer to the other person.

17. What is your Worst OCD Habit?
Assuming the person doesn’t actually have obsessive compulsive disorder, asking this question can inspire some real laughs and deep bonding.

18. Which bugs or animals are you most afraid of?
Nature can be scary and there is no shame in admitting your fears. This question will give you some insight into what creeps the other person out.

19. What Would You Name Your Child if You Hated them?
While this question might sound kind of mean, it can be a great chance to laugh with someone that you are trying to get to know.

20. What is the Worst Food You Have Ever Tasted?
We have all had experiences with eating gross foods, and maybe you dislike some of the same ones as them.

21. Do You Have Any Superstitions?
Whether it is holding your breath when you go by a cemetery or something else, a lot of people have weird superstitions that they follow.

22. What is something You Hate but Wished You loved?
For some people it is coffee while others try their best to like vegetables, but we all have things we hate that we wished we didn’t.

23. If you could make one mythical thing real, what would it be?
Is it a unicorn or maybe a dragon? This question can help you bond with the person in a very fun way.

24. What is Your Favorite Comedy Movie?
When you want to bond with someone in a funny way, there’s no better question that what their favorite comedy movie is!

25. What is Something You Can’t Seem to do Right?
Pretty much everyone has something that they cannot seem to do right no matter how many times they try, and learning what it is can be a good way to bond with someone new.


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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