Questions To Ask When Getting to Know Someone

The best questions to ask when getting to know someone are open-ended, easy to answer, and lead naturally into follow-ups. Focus on their interests (“What are you into lately?”), values (“What matters most to you in friendships?”), and current experiences (“What’s been the highlight of your week?”). Follow up with genuine reactions and deeper questions that show you’re listening.

Key Takeaways:

• Good questions to ask when getting to know someone are open-ended and invite stories, not one-word answers
• The best conversation formula is: ask, react with genuine interest, then expand with a thoughtful follow-up
• Start with easy warm-ups about their week or interests before moving to personal values or deeper topics
• Avoid interviewing them by mixing questions with your own short stories and matching their energy
• Use platform tools to stay safe when chatting online and keep personal info private at first

Meeting someone new can feel awkward. You want to learn about them, but you don’t want to sound like you’re reading from a script. The truth is, the best questions to ask when getting to know someone aren’t fancy or complicated. They’re simple, genuine, and give the other person room to share what matters to them.

This guide covers different question categories for every stage of getting to know someone, when to use them, how to avoid sounding like a job interviewer, and specific examples that work great in online chats. Whether you’re meeting someone at a party, in a class, or through a chat platform, you’ll have questions ready that actually lead somewhere good.

What Makes a Question “Good” When You’re Getting to Know Someone

Not all questions are created equal. Some kill conversations. Others open doors.

Open-ended beats yes/no almost every time. “Do you like music?” gets you nowhere. “What kind of music are you into right now?” gives them something to work with. That said, yes/no questions aren’t evil. Sometimes a quick “Did you catch that game?” works perfectly if you both follow the same team.

Low-pressure questions win. You’re not trying to get their life story in five minutes. You want questions that invite stories, not resumes. “What do you do?” puts people on the spot. “What’s keeping you busy these days?” feels way lighter.

Give them permission to pass. Not everyone wants to share everything right away, and that’s fine. Phrases like “if you’re comfortable talking about it” or “we can keep it light” show you respect boundaries.

The real goal isn’t to collect facts about someone. It’s to find a shared thread you can both pull on. One good question with solid follow-ups beats ten random ones that go nowhere.

The Simple Formula for Never Running Out of Things to Say

Here’s the secret: conversations die when you treat questions like a checklist. They come alive when you actually care about the answers.

Ask, React, and Expand

This three-step pattern keeps things flowing naturally:

1. Ask a question that’s easy to answer
2. React with something genuine – what surprised you, what you liked, or what you relate to
3. Expand with a follow-up that digs one layer deeper

Example: You ask, “What are you into lately?” They say rock climbing. You react: “That’s cool, I’ve always been scared of heights.” Then expand: “What made you want to try it?”

See how that feels like a real conversation? You’re not just firing questions. You’re building on what they give you.

The 2 Follow-Up Rule

When you hit a good topic, stay there for at least two follow-ups before jumping to something new. Too many people ask about hobbies, then immediately switch to work, then movies, then travel. It’s exhausting.

If someone mentions they’re learning guitar, ask what made them pick it up. Then maybe what kind of music they want to play. Two follow-ups show you’re actually interested, not just checking boxes.

Best Questions for First Conversations

First conversations need questions that are easy to answer and impossible to mess up.

Easy Warm-Up Questions

These work anywhere, anytime:

• “What’s been the highlight of your week?”
• “What are you into lately?”
• “How did your day end up going?”
• “What’s something you’re looking forward to?”

Notice how none of these put pressure on anyone. They’re invitations to share whatever’s on their mind.

Context Questions (Work Almost Anywhere)

Use what’s around you:

• “How do you know the host?”
• “What brought you here today?”
• “What made you pick this class or hobby?”
• “What do you usually do for fun around here?”

Context questions are cheat codes. They give people an easy starting point that relates to the moment you’re both in.

Questions That Reveal Personality Without Getting Too Personal

Once you’re past the warm-up phase, these questions help you learn what makes someone tick.

Interests and Hobbies

• “What hobby do you keep coming back to?”
• “What’s a show, game, or book you’ve been into recently?”
• “If you had a free Saturday, how would you spend it?”

These questions reveal what someone does when nobody’s telling them what to do. That says a lot about a person.

Taste and Preferences

• “What kind of music do you always return to?”
• “What’s your comfort food?”
• “Are you more of a planner or spontaneous?”

Preferences are low-stakes but surprisingly revealing. Someone who plans everything thinks differently than someone who wings it.

Small Opinions That Lead to Deeper Chat

• “What’s something you changed your mind about recently?”
• “What’s a hill you’ll politely die on?”

Opinion questions are gold. They let people share their thinking without getting heavy. Plus, they usually lead to fun debates or unexpected common ground.

Questions That Build a Real Connection

Ready to go deeper? These questions help you move from surface-level chat to actual connection.

Values and What Matters to Them

• “What do you value most in friendships?”
• “What’s something you’re proud of that most people wouldn’t guess?”
• “What’s a lesson you learned this year?”

When someone shares what they value, you learn what kind of person they are. These answers stick with you way longer than knowing their favorite movie.

Goals and Growth

• “What are you working on improving right now?”
• “What’s a goal you’re excited about?”
• “What’s something you want to learn next?”

People light up when talking about what they’re building toward. These questions show you care about where they’re headed, not just where they’ve been. For more on building meaningful conversations, check out our guide on conversation starters that actually work.

Light Personal Stories (Without Oversharing)

• “What’s a small moment that made you happy recently?”
• “What’s your favorite memory from the past few years?”

Stories beat facts every time. A good memory reveals personality, values, and what makes someone smile. Just keep it light at first.

Fun Questions to Keep It Playful

Sometimes you need to break the seriousness and just have fun:

• “If you could instantly get good at one skill, what would it be?”
• “What’s the most random thing you know a lot about?”
• “What’s your unpopular food opinion?”
• “If you could teleport anywhere for dinner, where are we going?”
• “What’s the best trip you’ve ever taken, or want to take?”

Playful questions remind both of you that getting to know someone should be enjoyable, not stressful.

Flirty Questions That Are Still Respectful

If there’s mutual interest and the vibe feels right, these questions can add a little spark without crossing lines.

When it’s appropriate to flirt: Look for signals – they’re laughing at your jokes, asking questions back, their body language is open. Timing matters. Save flirty questions for after you’ve built some rapport.

Questions that feel natural:

• “What’s your idea of a perfect weekend?”
• “What’s a trait you find attractive in people?”
• “What kind of date do you actually enjoy?”

What to avoid early on: Anything sexual, invasive, or that puts pressure on them. Keep it light and respectful. If they seem uncomfortable, dial it back.

Deep Questions for When the Vibe Is Right

Some conversations naturally go deeper. When you’re both comfortable and the trust is there, try these:

• “What’s something you wish more people understood about you?”
• “What does a good life look like to you?”
• “What’s a challenge that shaped you?”
• “What do you want more of in your life right now?”

How to keep it safe: Share a little about yourself too. Give them permission to opt out (“We can talk about something else if you want”). Deep questions work best when both people feel safe being honest. According to Psychology Today, vulnerability in conversations builds stronger connections, but timing and mutual comfort are everything.

Questions to Ask Online, Especially in 1-on-1 Chats

Online conversations need different openers because you can’t read body language or use the space around you.

Openers That Beat “Hey”

• “What are you hoping to talk about today?”
• “Pick one: music, movies, travel, or goals?”
• “What’s an interest you could talk about for hours?”

These give people direction. “Hey” leaves them guessing what you want.

Using Interest-Based Prompts

Shared interests make conversations smoother from the start. If you’re meeting people through 1-on-1 chat platforms like Emerald Chat, starting with shared interests helps you skip the awkward small talk and jump into real conversation.

When platforms let you filter by interests, use them. Talking to someone who already likes the same stuff you do cuts out half the work.

How to Move from Chat to Real Connection Safely

Keep personal info private at first. Don’t share your full name, address, or other identifying details until you’ve built trust.

Suggest low-stakes next steps: sharing a link to something you both like, setting a time to chat again, or moving to a topic you’re both curious about. Take it slow.

How to Avoid Sounding Like You’re Interviewing Them

The fastest way to kill a conversation is turning it into an interrogation. Here’s how to avoid that:

Mix questions with short personal shares. After they answer, add a quick story of your own. “That’s cool, I tried yoga once and fell asleep during the relaxation part.”

Use statements that invite response. Instead of “Do you like travel?” try “I’ve been thinking about planning a trip somewhere new.” They’ll jump in if they’re interested.

Don’t stack three questions in a row. If you catch yourself asking question after question, stop. Say something instead. React to what they just told you.

Match their energy and pace. If they’re giving short answers, they might need time to warm up. If they’re writing paragraphs, match that energy. For more tips on reading conversation flow, check out our post on how to keep conversations interesting.

Red Flags and Boundary-Friendly Questions

Not every conversation goes well. Watch for warning signs.

Red flags: They avoid every question, make fun of your interests, or pressure you to share things you’re not ready to talk about. Trust your gut.

Boundary questions you can ask:

• “Are you comfortable talking about that?”
• “Want to keep it light or go deeper?”

These show you respect their comfort zone. If someone ignores your boundaries, that tells you everything you need to know about them.

Stay safe online: Use reporting and moderation tools on platforms like Emerald Chat if someone is disrespectful or pushy. You don’t owe anyone your time if they make you uncomfortable.

Quick List You Can Copy and Use

10 First-Chat Questions:

1. What’s been the highlight of your week?
2. What are you into lately?
3. How did your day go?
4. What brought you here today?
5. What do you do for fun?
6. What’s something you’re looking forward to?
7. How do you know [person/place]?
8. What made you pick this [hobby/class/event]?
9. What kind of music are you into?
10. What’s your go-to comfort food?

10 Connection-Building Questions:

1. What do you value most in friendships?
2. What’s something you’re proud of?
3. What’s a goal you’re working toward?
4. What’s something you want to learn?
5. What’s a lesson you learned recently?
6. What matters most to you right now?
7. What hobby do you keep coming back to?
8. What’s your ideal Saturday look like?
9. What’s a challenge that shaped you?
10. What’s something people wouldn’t guess about you?

10 Fun Questions:

1. If you could teleport anywhere for dinner, where?
2. What’s your unpopular food opinion?
3. What’s the most random thing you know a lot about?
4. If you could instantly master one skill, what?
5. What’s the best trip you’ve taken?
6. What’s a show you’ve been binging?
7. What would your dream weekend look like?
8. What’s something you’ve changed your mind about?
9. What’s a hill you’ll politely die on?
10. If you had a free day, how would you spend it?

10 Deeper Questions:

1. What’s something you wish people understood about you?
2. What does a good life look like to you?
3. What do you want more of right now?
4. What’s your favorite memory from the past few years?
5. What kind of person do you want to become?
6. What’s something you’re working on improving?
7. What makes you feel most alive?
8. What’s a value you won’t compromise on?
9. What’s been on your mind lately?
10. What’s a small moment that made you happy recently?

Final Thoughts

Getting to know someone doesn’t require a perfect script. It needs curiosity, follow-ups, and genuine interest in their answers. Good questions open doors, but your reactions and follow-ups are what turn small talk into real connection.

Here’s your challenge: next time you meet someone new, ask one open-ended question. Do two thoughtful follow-ups that show you listened. Then suggest a next step, whether that’s continuing the conversation another time or diving into a topic you’re both excited about.

Ready to practice these conversation skills? Try Emerald Chat for free 1-on-1 conversations where you can meet new people and test out these questions in a safe, moderated environment. Start with shared interests, ask better questions, and build real connections.

Frequently Asked Questions

What are good questions to ask someone you just met?

Start with easy, low-pressure questions like “What’s been the highlight of your week?” or “What are you into lately?” These give people room to share what they want without feeling interrogated.

How do I avoid awkward silence when getting to know someone?

Use the ask-react-expand formula. After they answer, react genuinely to what they said, then ask a follow-up that goes one layer deeper. Stay on good topics for at least two follow-ups before switching subjects.

What questions help you connect with someone quickly?

Questions about values, goals, and what matters to them build connection fast. Try “What do you value most in friendships?” or “What’s something you’re working on right now?” These reveal who someone really is.

How do I know if I’m asking too many personal questions?

Watch their responses. Short answers, changing the subject, or hesitation mean you’ve gone too deep too fast. Always give people an out with phrases like “We can keep it light if you want.”

What are the best questions for online chats?

Online, skip “hey” and start with direction: “What’s an interest you could talk about for hours?” or “Pick one: music, movies, or travel goals?” Interest-based questions work great because you’re both there to connect anyway.

How can I tell if someone wants to go deeper in conversation?

They’ll share details you didn’t ask for, ask questions back, and stay engaged. If they’re only giving one-word answers, stick to lighter topics. Match their energy and let them guide how deep it goes.