Questions to Get to Know Someone

Want to get to know someone better? Then ask them some thoughtful questions.

Forging strong relationships with others makes for a richer, more fulfilling life. And as human beings, we crave connections with other human beings. Even science says that having strong friendships is good for our health. 

It’s also worth it to deepen the relationships you already have. Think of your parents, family members, and close friends. Just because you’ve known them for ages doesn’t necessarily mean that you know everything there is to know about them. 

But in today’s modern world, where a lot of our daily interactions take place in front of a device, and interesting conversations have been replaced by texts and DMs, it feels nearly impossible to get to know someone in a more meaningful way. 

And if you’re more of the introverted type, then trying to strike a conversation with someone comes with its own pressures and anxieties. How do you know what to say? And how do you break the ice and ask questions without sounding like you’re cross examining a witness? 

Fortunately, you don’t have to be a social butterfly or extroverted type to engage in a meaningful conversation. You just have to be yourself. And with the right questions, you can get to know anyone better–even the people you’ve known forever.

Below are some questions you can ask to get to know someone better. Whether you’re trying to deepen your relationships with friends or loved ones, or strike up a conversation with people at work, asking questions will help you break the ice and get to know them better. 

Questions to get to know your mom better

How well do you know your mom? Maybe you have a close relationship with your mom or maybe you’re hoping to get to know her better. Asking her questions about herself will help you learn new things about her and even see her in a new light. 

These questions would make for a fun and interesting conversation around Mother’s Day or her birthday, or whenever you’re spending time with her. 

• What did you want to be growing up?

• What was your first job?

• Who was your favorite teacher?

• Did you ever get up to any mischief as a kid?

• What’s your dream vacation?

• Who was your first love?

• What was your proudest achievement?

Questions to get know your dad better

We all know the stereotypes about dads. That they like to barbecue, drink beer, work on their cars, etc. But what does your dad really like to do? Whether your dad is an open book or more of the introverted type, asking him thoughtful questions can get him to open up more. 

Here are some fun and interesting questions that you can ask your dad and get to know him better. 

• What was your childhood home like? 

• Who was your best friend going up?

• What was your relationship like with your parents?

• Did you have any childhood pets?

• What are you most proud of?

• Tell me about your travel adventures. 

Questions to deepen your friendships

Your close friends always know how to make you laugh till you cry.  And they’re always there for you when you need them most. 

But as we get older, and move to different cities or different stages in our lives, it can feel challenging to maintain our close friendships. So the next time you’re hanging out or writing them a note, ask them some playful and introspective questions so that you can catch up and get to know them even better. 

• What’s your favorite childhood memory?

• What do you miss most about college?

• What was your worst job?

• What was your favorite job?

• What’s a quirk or idiosyncrasy that you have that no one else knows about?

• If you could live anywhere in the world, where would it be?

• What book can you read over and over again?

Questions to get know your boss or coworkers 

Having office friendships is key to liking your job and feeling happy at work. Afterall, you can’t work in a vacuum. You need other people to help brainstorm creative ideas with or to problem solve or to just vent to after a tough day in the office. 

But building a strong relationship with your boss or coworkers can also be a bit of a challenge. You want to get to know them better, but you also want to make sure you’re being professional about it. So here are some questions you can ask to get to know the people in your office better, while also being respectful and considerate.

• What was your first job like?

• What was your proudest achievement outside of work?

• What was your biggest work challenge?

• What do you do to decompress after work?

• What’s your secret superpower?

• Where’s your favorite place to travel?

• If you could have any job in the world what would it be?

Questions to ask someone at a party or social setting 

Making new friends as an adult can be hard. Everyone already seems to be part of an established friend group and it can be tough getting to know a stranger at a party or social event.

But it’s important to remember that everyone else probably feels the same way you do. And they also feel awkward at parties! One way to make the conversation feel more natural and fun is to frame it around recommendations. People love recommending their favorite movies or restaurants and it’s an easy way to quickly establish that you have something in common. 

So here are some conversation starters to help you engage in a conversation with someone new at a party or social situation. These questions can organically get a conversation going without feeling like you’re interrogating the other person. 

• How do you know the hosts? (It’s less intimidating to talk o a stranger when you have a mutual friend in common.)

• What’s your go-to restaurant or bar? (This is especially helpful if you’re new in town!)

• Do you have any fun vacation plans coming up? Follow up question: Where are your favorite places to travel?

• Are you watching any fun shows or binging anything at the moment? 

• Do you have any recommendations for things to check out on the weekends?

Written by JiJi Lee