8 Questions to Get to Know Someone

Getting to know someone isn’t always easy. Sometimes it happens naturally, and the conversation flows; sometimes, you have to put in a little work to get them to open up, or you have to get out of your comfort zone yourself. Sometimes it’s something in between. Either way, you can’t get to know someone without being curious and asking questions.

But what are the right questions? If you’re still trying to figure that out, you’re not alone. We’re all individuals with unique personalities, so it’s hard to say there are any right or wrong questions to get to know someone. But there are certainly some that seem to get the conversation flowing better than others. So whether you’re preparing for a date, going to lunch with a colleague, or looking for things to talk about on FaceTime, here are a few prompts that might jumpstart the conversation for you.

Easing in: Conversation Starters

No matter how curious you are, you can’t go too fast too soon. If you really want to get to know someone, it’s best to start with some more surface-level questions to make each of you comfortable in the beginning. These questions work in person, but they’re also great things to talk about on FaceTime if you’re getting to know someone virtually.

Ask About Their Work

Work is typically a safe topic, to begin with. It’s not too personal, it’s not risque, but most people will have at least something to say about it, whether they love their job, hate their job, or are indifferent. Plus, people spend much of their days working; it’s genuinely interesting to get an idea of what those days look like.

What Do You Do for Fun on Your Days Off?

If you start with a conversation about work, this is a simple transition to make that will turn the conversation in a slightly more personal direction. What people do in their free time says a lot about them, whether they go explore a city, find a park and read a book, or even just hang out at home and take advantage of the time to relax. This question can also keep the conversation rolling on its own, as depending on the answer, you may have a lot more follow-up questions to ask.

Tell Me About What You’re Watching or Reading Right Now

If there’s one thing I’ve learned about talking to new people, it’s that talking about shows, movies, and books is almost always a bonding experience. People love to talk about whatever media they’re consuming at the time. It’s social and relatable, and if you have a shared interest in a show or other form of media, it gives you an automatic connection.

It also may seem simple or surface-level, but what kind of media people are consuming says a lot about their taste. Not everybody reads books for fun so that in itself is revealing, as is someone’s genre of choice for any kind of media. Do they enjoy horror, or do they opt for lighter options, like rom-coms? Talking about entertainment is nearly always a sure way to measure up your interests and what you have in common.

What’s Your Favorite Place to Eat?

If there’s one thing people love talking about as much as entertainment, it’s food. Food can be a casual topic of conversation, just about the best spots in town for different occasions, or it could go deeper and turn into something more revealing, more cultural. Either way, you spin it, it’s a great conversation starter that could even eventually lead to a meal at one of those places together.

Take Things Up a Notch

Once you’ve gotten past the lighter topics, you can judge whether or not it’s time to dig a little deeper. If things are going well, you can start asking each other questions that are a little less surface-level and require more thought and personal information. This is the next step in getting to know someone. If you’re looking for things to talk about over FaceTime, you shouldn’t necessarily start with these at risk of coming off a little gauche. But that doesn’t mean you can’t ease into them after you get past some small talk!

What’s Your Dream Job?

This question is actually more than just a surface-level icebreaker because it’s a chance at a little vulnerability. When someone answers this question honestly, it not only reveals some of their deeper passions but also shows whether they’re pursuing their dreams, has plans to pursue their dreams, or have deemed them unattainable. It can begin a much deeper conversation about careers, futures, and passions that can really allow you to get to know someone.

Tell Me About Your Best Friend.

This question allows someone to open up, but without it feeling like it’s about themselves. The company people keep saying a lot about them, but so does how they talk about them. This topic can reveal a lot about how this person is emotional; do they gush about a friend, or do they keep it short and sweet? Do their friends sound like people you’d get along with? This topic will not only get them talking but can get you thinking as well.

What’s Your Guilty Pleasure?

Asking someone’s guilty pleasure is fun, lighthearted, and quite literally forces them to admit something to you that they don’t generally freely admit to others. At least, that’s the case if they’re telling you their guilty pleasure. It can be funny and even a little embarrassing, but it’s also a great chance to bond and get to know someone. Plus, you might find you have some of the same ones, like dipping french fries in a milkshake. Who knows!

Are You Close with Your Family?

This is one you’ll want to save until you really feel things are going well. It can be an easy question for some, but for others, it may be more difficult to answer. Either way, it’s a fairly personal question that will either open this person up a lot or close them off. So before you fire off questions about family, try to get a read on how the situation is going. And this isn’t necessarily a topic to talk about over FaceTime unless there are no other options; it’s usually better in person.

Getting to Know Someone on Facetime?

No problem. As we’ve mentioned, most of these topics are great for FaceTime. It’s nice to have some things to talk about on FaceTime planned out ahead of time to avoid awkward silences and to keep the conversation flowing since you have to put in a little more work when it’s virtual. But if you’re looking for other ideas, there are a lot of virtual activities you can do on FaceTime that is great for all ages.

If you’re getting to know a younger family member but have to do so from afar, there are apps and programs that can connect you both to various games and activities, giving you plenty of things to do on FaceTime. If it’s an adult, you can have a happy hour together or even host a game night with others.

At the end of the day, getting to know someone, whether you’re on FaceTime or in real life, is all about opening up and getting that person to do the same. If you’re open, it encourages them to follow suit. So ask questions that seem appropriate for the tone of your conversation and be patient. You could have a new friend (or more!) before you know it.