conversation starters

33 Killer Conversation Starters to Spark Dazzling Conversations with Anyone

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conversation starters, social skills, networking tips, deep conversation questions, small talk alternatives

Want to master the art of conversation? Here are 33 killer conversation starters to help you connect with anyone, from strangers to friends, in any setting. These engaging questions ditch boring small talk like “Where are you from?” or “What do you do?” and create memorable, meaningful interactions.

Killer Openers: Break the Ice with Ease

These conversation starters are perfect for meeting someone new or reconnecting with an acquaintance, offering fresh alternatives to standard questions.

  • Tell me about you.
    this is a great one because it invites the other person to tell you something that they want to share if they want to tell you about their job they can if they want to tell you about their kids they can and it’s a great way to know what’s at the top of someone’s mind
  • Working on anything exciting recently?
    this is my alternative to what do you do asking if someone is working on anything exciting helps the other person talk about something good in their life as opposed to just giving you a boring update
  • What’s your story?
    this is an interesting conversation starter because it invites someone to tell you a story about themselves and you never know what exciting thing they might tell you
  • What personal passion project are you working on right now?
    this is one of my favorites you never know what secret side hustle someone has I love asking this one to people I already know in one context like work but would love to know more about them personally
  • How do you know the host?
    this one can be modified to any kind of event if you’re at a party hopefully you both have the host in common if you’re at a networking event or work party you can modify it – how long have you been a part of this organization
  • What was the highlight of your day today? / What was the highlight of your week?
    these are both great ones to ask instead of the standard how are you or how’s it going it also helps people share a positive story instead of just an autopilot answer of fine good
  • Have you been to an event like this before?
    this one can be modified for most types of vents from birthday parties did you come last year to networking events do you come every month
  • What was the High Point and low point of your day so far?
    this one is great if you have a talker if you’re speaking with an extrovert asking questions for them to ruminate and expand will tickle their fancy extroverts love this question
  • Has this been a busy time for you?
    I don’t always like to ask people about being busy but I use this conversation starter if someone seems distracted or not engaged sometimes acknowledging their busyness can hook them in
  • How’s that drink appetizer artwork game?
    one of my favorite context cues is asking about whatever someone is holding or doing ask them about their wine ask them if they like the artwork ask them if the food is good these are very easy openers
  • Having fun?
    a really easy cold approach opener is to look for someone who is by themselves but looks like they’re having an okay time it’s easy to sit next to someone at a table or stand next to someone at the bar and simply ask having a good time or enjoying yourself it’s a nice opener and better than just how are you

Getting Personal: Deepen the Conversation

These questions help sustain a conversation, moving from small talk to more personal topics.

  • What are you doing this weekend?
    ever had that awkward lull in a conversation this conversation starter is always welcome and if it’s a monday or tuesday you can modify to ask did you do anything fun this past weekend sometimes I also try what’s your favorite thing to do on the weekends
  • What are your favorite restaurants around here?
    I almost always ask for personal recommendations they make great conversation starters why I always get great tips and if someone doesn’t have an answer because they’re new to a city you can always talk about where they came from
  • When win keeping up with sport TV show news?
    if you’re up-to-date on news or sports you could also ask your partner if they keep up as well if so great you have a lot in common if not you can tell them about it
  • Can you recommend any unique cocktails appetizers desserts?
    another great way to get recommendations is asking what to order or grab from the buffet if they haven’t eaten yet you can go grab some food together
  • All the foods looks so good I’m not sure what to get what are you thinking or what have you tried?
    a variation of asking for recommendation is asking simply for advice on what to order even at networking events you could walk up to the bar to get recommendations
  • What a beautiful cool ugly bizarre venue have you been here before?
    one thing you will always have wherever you are is context whether you’re in a house a restaurant or a ballroom there’s always something unique to comment on and ask about
  • Did you see that viral YouTube video it was all over my social media today?
    if there is a great video or meme you just watched bring it up show them my video if they have seen it you can laugh together if they haven’t you can show them

Deep Conversation Starters: Build Stronger Connections

For longer interactions or with familiar people, these questions foster deeper, more meaningful conversations, as outlined in Captivate’s three interaction phases: first five minutes, first five hours, and first five days.

  • If you had to pick any character in a book movie or TV show who is most similar to you who would you choose why?
    this is a great one if someone has just talked about an actor or book or movie it tells you a lot about a person to hear which character they feel most like
  • When you were growing up what was your dream job is any part of that still true?
    I love asking this one any time someone has just mentioned something about their own childhood or growing up it also helps you to talk about their current job and if it’s similar to their original dream
  • What’s your biggest fear?
    ooh this one’s deep but so good it always sparks great conversation
  • What’s your biggest regret?
    talking about regret can really help you get to know someone and there past only ask this if you really want to get to know them
  • Who is your role model?
    if you’re talking about an inspiring person or boss or author you might be able to ask the person about their role model this is a great way to talk about who inspires you

Event-Specific Conversation Starters: Make It Timely

These holiday- or event-based questions add a fun, relevant spin to conversations.

  • January: what’s your new year’s resolution
  • February: do you usually celebrate Valentine’s Day do you think it’s a real or fake holiday
  • March: I went to the coolest Irish bar last st. Patrick’s Day doing anything fun this year
  • April: how long did you believe in the Easter Bunny
  • July: what’s the best fireworks display you’ve seen on the fourth of July
  • October: what’s the best Halloween costume you ever had or do you like haunted houses or scary movies
  • November: what’s your favorite Thanksgiving dinner food
  • December: how does your family celebrate for the holidays
  • Birthday-specific:
    • so the birthday person what was the highlight of your last year or what do you want to achieve for next year
    • to follow celebrators how do you usually celebrate your birthday or what was the best birthday you ever had
    • to everyone what was the best or worst birthday gift you ever received this is a great one to do around a dinner table the answers are always hilarious

Tips for Mastering Conversation Starters

  • any and all of these conversations orders will work for you if you are courageous enough to drop the boring ones and get to the good ones most people are so relieved to have you start and continue the personally
  • remember you also want to have your answers to these questions ready to go if someone doesn’t know their answer you can jump in with yours to make them feel more comfortable good luck can’t wait for you to have your next convo

Take Your Conversation Skills Further

hey I want to tell you one more thing you are amazing the question is do you know how to share it I’d love to help I saved my very best tips for my insider subscribers subscribe for free at science at people.com I know your inbox is sacred so I promise to send you only emails want more conversation tips sign up at science of people.com slash conversationalist to get our free mini course three steps to amazing conversation I want to make you an excellent conversationalist

FAQ: Common Questions About Conversation Starters

1. What are the best conversation starters for meeting new people?
Use openers like “Tell me about you” or “Working on anything exciting recently?” to invite engaging, personal responses that avoid generic small talk.

2. How can I keep a conversation going without awkward pauses?
Ask follow-up questions like “What are you doing this weekend?” or use context cues, such as “How’s that drink?” to maintain a natural flow.

3. What are deep conversation starters for building stronger connections?
Try questions like “What’s your biggest fear?” or “Who is your role model?” to transition to meaningful topics with friends or acquaintances.

4. How do I start conversations at networking events or parties?
Leverage context with questions like “How do you know the host?” or “What a cool venue, have you been here before?” to break the ice.

5. What are good conversation starters for holiday or birthday events?
Use timely questions like “What’s your New Year’s resolution?” (January) or “What was the best birthday gift you ever received?” for festive, relevant chats.

6. How do I make conversations feel natural and authentic?
Be courageous, use context (e.g., venue, food), and have your own answers ready to share, making others feel comfortable and engaged.

20 Deep Conversation Starter Questions for a Great First Date

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20 Deep Conversation Starter Questions for a Great First Date

Namaskar, First dates can feel like a tightrope walk—exciting but a little nerve-wracking, especially when it comes to keeping the conversation going. You want to get to know your date without turning it into an interrogation room. These questions are all about digging deeper, finding common ground, and keeping things authentic, so you can see if there’s a real connection worth pursuing. Plus, I’ve added an FAQ at the end to tackle common first-date conversation worries.

Why These Questions Make a Difference

A first date isn’t just about filling the silence—it’s about learning who someone is, what they value, and if you vibe together. Courtney says asking the right questions can show you if you’re compatible in values, goals, and personality without making it feel like a job interview with cocktails. These 20 questions, taken directly from her videos, help you avoid awkward, one-word answers and get to stories, passions, and real talk that make a date memorable.

20 Deep Conversation Starter Questions

1. What Made You Interested in Going Out with Me?

This one’s a flirty way to start, asking what caught their eye—maybe something on your dating app profile or a moment you shared. Courtney says to ask it in a joking way, like “What made you swipe right?” It’s a fun, light question that shows what they’re into and can kick off a good conversation.

2. What Are You Looking for?

This gets straight to the point: are they after a casual fling or a serious relationship? Courtney’s big on believing their answer. If they say they just want a hookup and you’re looking for something long-term, don’t try to change their mind—it’s a time-saver to know early.

3. What Matters to You?

Instead of asking something narrow like “What are your hobbies?” this broad question lets them share what’s important—family, work, or maybe a passion project. Courtney says it’s a great way to learn their values without boxing them into a specific answer.

4. What Are You Most Passionate About at the Moment?

This is all about finding their “golden nugget”—that thing they light up talking about. Courtney loves this because it could be a new workout class, a TV show, or a side hustle, and it makes the conversation flow easily while showing you who they are.

5. When You Think of a Recent Big Political Event, Is There Something That Stands Out to You?

This question tests if they’re tuned into the world without going full-on political debate. Courtney says it can show if your views align and how much they care about what’s happening, which might matter to you.

6. What Does Your Work-Life Balance Look Like?

This digs into how they juggle work and personal life, which Courtney says hints at whether they can make time for a relationship. A softer way to ask might be, “What do you do when you get off work?” to see if they’re always working or prioritize downtime.

7. What Does Your Life Look Like 5 Years from Now?

This one’s about their big-picture goals—family, career, or travel. Courtney points out that if their vision (like no kids for 10 years) doesn’t match yours (wanting a family soon), you might not be compatible, and that’s okay.

8. What Would You Do If You Had a Week Off?

A fun way to learn what they love doing, this question shows if they’d travel, chill with their dog, or dive into a hobby. Courtney says it reveals their vibe and opens the door to more questions, keeping the chat lively.

9. When You Spend Time with People, How Often Are You the One Making Plans?

This shows if they take the lead or sit back in relationships. Courtney likes it because it reveals their communication style—planners might be reliable, while someone who never plans could leave you carrying the load.

10. How Well Do You Feel Like You Compromise with Others?

This can feel a bit like a job interview, but it’s about seeing if they’re flexible. Courtney suggests watching how they act—like if they insist on their choice of appetizer—or asking, “What’s a time you met someone halfway?” for a less formal vibe.

11. What Do You Think Is Important for a Healthy Relationship?

This gets them talking about values like communication or trust. Courtney warns that if they only mention something like sex, it might be a red flag if you’re after deeper connection. Watch their actions, too, not just their words.

12. How Do You Handle Conflict?

This tests if they’re self-aware about resolving disagreements. Courtney says it can feel buttoned-up, so you might try, “What do you do when you disagree with someone close?” If they say “I don’t know,” that’s a clue they might struggle with conflict.

13. What Is Something in Past Relationships You Needed to Work On?

This checks if they reflect on themselves. Courtney says if they blame their ex for everything, it’s a red flag. She suggests asking this on a second or third date so it doesn’t feel too heavy right away.

14. Who Is the Person You Talk to the Most?

A cute, light question that shows who they value—maybe their mom, best friend, or sibling. Courtney loves how it brings out stories and keeps things relaxed between deeper questions.

15. What Is the Best Gift You’ve Ever Received?

This fun one reveals what they cherish, like a thoughtful handmade gift or a fancy gadget. Courtney says it can lead to stories about their interests, like training for a race, and keeps the vibe easygoing.

16. What Was Your First Impression of Me?

Ask this when the date’s going well to see if they’ve been paying attention. Courtney suggests waiting for a second date to avoid awkwardness, but it’s flirty and shows how they see you.

17. What Made You Most Excited About Going on a Date with Me?

This is like the first question but focuses on what they were looking forward to. Courtney says it can lead to fun follow-ups like “What’s something totally random you’d like to know about me?” to keep things flowing.

18. What’s Something Totally Random You’d Like to Know About Me?

This playful question, straight from Courtney’s advice, brings out quirky facts or hidden talents. It’s a great way to add humor and balance out the deeper stuff.

19. What’s a Project You’re Working On That You’re Excited About?

Inspired by Courtney’s tip to dig into passions, this question gets them talking about something they’re into right now, like a creative project or a fitness goal, to spark an enthusiastic chat.

20. What’s Something You Do for Fun on the Weekends?

Courtney suggests asking about free time to see their lifestyle and interests. This question reveals what they enjoy outside work, like hiking or binge-watching a show, and helps you see if your vibes match.

How to Make These Questions Work

Courtney’s tips from her videos help you use these questions to keep things natural and engaging:

  • Prepare a Little Bit: Have a few questions in your head as a backup, but don’t script the whole date. Courtney says it’s like having a plan for an interview—just enough to feel at ease.
  • Ask the Right Questions: Go for open-ended ones that lead to stories, not one-word answers. Courtney says this makes the conversation snowball naturally into deeper topics.
  • Find Their Golden Nugget: Look for that thing they light up about and dive in. Courtney learned this from sorority recruitment—it makes them feel heard and keeps the chat effortless.
  • Tell Her About Yourself Too: Share your own experiences to make it a two-way conversation. Courtney says finding commonalities makes things more comfortable and natural.
  • Silence Is Normal: Don’t panic over brief pauses. Courtney says they’re okay and can even make the date feel more like you already know each other.
  • Be Authentic: Be yourself, not someone you think they want. Courtney says this helps you attract someone who likes the real you, making the connection genuine.

Why These Questions Are Great

These 20 questions come straight from Courtney’s videos, blending fun and depth to help you learn about your date’s values, passions, and lifestyle. They’re designed to avoid the interrogation feel, encourage storytelling, and show you if you’re a good match. Whether you’re digging into their dreams or laughing over a random fact, these questions set the stage for a date that feels real and leaves you both wanting more.

Wrapping It Up

First dates don’t have to be stressful. With these 20 conversation starters from Courtney Ryan’s videos, you’ve got a toolbox to spark meaningful, natural chats. From finding out what matters to them to sharing a laugh over a quirky question, these prompts help you see if there’s a connection worth chasing. Pick a few, stay yourself, and let the conversation roll. Let me know in the comments what questions you love for first dates or if you’ve tried any of these!

FAQs About First-Date Conversation Starters

Q: How many questions should I ask on a first date?
A: Don’t rapid-fire a bunch of questions. Courtney says to pick a few good ones—maybe three to five—and let them flow naturally so it doesn’t feel like an interrogation.

Q: What if they give short answers?
A: Try a follow-up like “What made you want to do that?” Courtney says if they’re still not engaging, it might mean you’re not clicking or they’re not into the conversation.

Q: Should I steer clear of politics or past relationships?
A: Courtney says a question about a recent event can show their values without getting too heavy, but save past relationship talk for a second or third date to keep the focus on you two.

Q: How do I keep it from feeling like a job interview?
A: Share your own stories and build on their answers. Courtney says finding their golden nugget—the thing they love talking about—makes it feel more like a real conversation.

Q: What if we run out of things to say?
A: Have a couple backup questions ready, and don’t sweat small silences. Courtney says pauses are normal and can actually make things feel more comfortable.

Q: Can I use these questions when texting?
A: Totally. Courtney says these tips work for texting too. Ask open-ended questions like “What are you passionate about right now?” to keep things interesting online.

Top 7 Best Conversation Starters –  Tricks to Start Any Conversation

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Starting a conversation with a woman you find attractive can feel daunting, but it doesn’t have to be. With the right approach, you can break the ice confidently and naturally. In this guide, we’ll explore seven tried-and-true conversation starters that work in any situation, helping you connect with ease and charm. Whether you’re at a coffee shop, a party, or just walking down the street, these techniques will ensure you never miss an opportunity to talk to someone you like.

Why Conversation Starters Matter

Approaching a woman without a plan can lead to overthinking, nervousness, or missed opportunities. Having a few go-to conversation openers in your pocket can boost your confidence and make the interaction feel effortless. These seven methods are designed to be simple, natural, and effective, allowing you to start a conversation without feeling awkward or forced.

1. Disarming Questions

A disarming question is a simple, easy-to-answer question that breaks the ice without putting pressure on the other person. Examples include asking for directions or inquiring about a nearby coffee shop. For instance, you might say, “Excuse me, do you know where the nearest Starbucks is?” The key is to follow up with a relaxed segue, like, “Thanks! By the way, where are you from?” This transitions the chat into a natural conversation, allowing you to get to know her better.

2. Prop-Based Opener

Comment on something she’s holding, wearing, or something in your shared environment. At an art gallery, you might say, “Wow, that painting is amazing,” or at a bar, “What are you drinking? Is it good?” This approach is easy because it’s based on observation. Once she responds, introduce yourself to keep the conversation flowing. It’s a low-pressure way to start talking without needing to be overly clever.

3. Situational Opener

Similar to the prop-based opener, this method involves commenting on what’s happening around you. If you’re at a bar with a loud band, you could say, “Have you heard these guys play before?” or “It’s a bit loud in here, isn’t it?” In a boring college lecture, you might whisper, “This is so dull—what would you rather be doing right now?” These observations are relatable and open the door to further conversation.

4. Opinion Opener

Asking for her opinion or advice is a classic and engaging way to start a conversation. At a coffee shop, try, “I’m new here—what’s your recommendation for a drink?” Or at a clothing store, hold up a shirt and ask, “Would this look weird on me?” Opinion openers spark engagement because they invite her to share her thoughts, making it easy to transition into a deeper conversation.

5. Cold Read

A cold read involves making a general guess about her personality, background, or emotional state. For example, at the gym, you might say, “You don’t look like you’re from this neighborhood.” Or at a social event, “You seem like a creative person with an artistic vibe.” Keep it general to avoid being creepy. This approach works because it’s unique, personal, and sparks curiosity, encouraging her to respond and engage.

6. Social Opener

In social settings like parties or networking events, simply walk up and say, “I don’t think I’ve met you yet—my name’s [Your Name].” This line implies you’re a social, well-connected person, boosting your perceived confidence. It also sets the stage for a conversation by removing awkwardness and signaling that you’re ready to chat. It’s simple but highly effective.

7. Direct Opener

The direct opener is bold and powerful: “Hey, I know this is random, but I think you’re really cute, and I wanted to meet you.” This approach exudes confidence and clearly states your interest, reducing the chance of being friend-zoned. Delivery is key—project your voice, maintain open body language, and smile. Even if she’s unavailable, she’ll likely respect your courage, and if she’s single, this can spark instant attraction.

Take Your Conversations Further

These seven openers give you the tools to start a conversation with any woman, anywhere. To keep the chat engaging, focus on being observant, relaxed, and confident. If you want to master the art of continuing conversations, making women smile, and building attraction, consider exploring additional resources like the Banter Guide, which offers tips and techniques for playful, engaging interactions. Check it out at [insert link] for more insights on dating with confidence.

Start practicing these openers today, and you’ll never miss a chance to connect with someone special. Keep it natural, be yourself, and watch your confidence soar!

33 Easy Conversation Starters to Make Any Chat Fun

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Ever walk into a room and feel stuck on what to say? We’ve all been there, fumbling with “So, where you from?” and getting nowhere. These 33 conversation starters are like your secret weapon for turning awkward moments into fun, real chats—whether you’re at a party, catching up with a friend, or meeting someone new at a coffee shop. They’re fresh, easy to use, and way more interesting than the usual small talk. Let’s get you chatting like a pro!

Friendly Icebreakers to Kick Things Off

These are perfect for starting a conversation with someone new or reconnecting with someone you haven’t seen in a while. They feel natural and get people opening up.

  • “Tell me about you!”
    It’s like handing them a blank canvas—they can share whatever’s on their mind, from their favorite hobby to their latest adventure.
  • “Doing anything fun lately?”
    A chill way to skip the boring “What’s your job?” and get them talking about something they’re excited about.
  • “What’s your story?”
    This one’s a gem—it invites them to share a piece of their life, and you might hear something totally unexpected.
  • “Got any cool side projects going on?”
    I love asking this to learn about someone’s passions, especially if you only know them from work or school.
  • “How do you know the host?”
    Works at any event—swap it out for “How’d you end up in this group?” at a meetup or club.
  • “What’s been the best part of your day?”
    So much better than “How’s it going?”—it nudges them to share a happy moment.
  • “You come to events like this a lot?”
    Easy to tweak for any setting, like “Were you at last year’s party?” or “Do you hit up these meetups often?”
  • “What’s been the high and low of your day?”
    If they love to talk, this one’s perfect—it gives them room to share a story.
  • “Things been crazy for you lately?”
    Great for someone who seems a bit distracted—it shows you’re paying attention and invites them to open up.
  • “How’s that drink/snack/vibe here?”
    Look around and use what’s there—comment on their coffee, the decor, or the food to ease into a chat.
  • “Having a good time?”
    Spot someone chilling by themselves? This is a simple, friendly way to start without being awkward.

Questions to Keep the Vibe Going

Once you’re past the hello, these keep the conversation flowing without any weird pauses.

  • “Got any fun weekend plans?”
    If it’s Monday, try “What’d you get up to last weekend?” It’s a safe bet that always sparks something.
  • “What’s your favorite spot to eat around here?”
    People love sharing their go-to places, and you might find a new favorite restaurant.
  • “You keeping up with [that new show/game/trend]?”
    If you’re into sports or pop culture, ask if they are too. If not, share a quick story to keep it rolling.
  • “Any food or drink here you’d recommend?”
    Awesome at events—ask about the menu, and maybe you’ll end up grabbing something together.
  • “This place is so [cool/quirky/nice]—you been here before?”
    The setting’s always a great conversation starter. Just comment on the vibe or surroundings.
  • “Caught that viral video everyone’s talking about?”
    Bring up a funny clip or meme—if they haven’t seen it, you can show them for a quick laugh.

Deeper Questions for Real Connections

When you’re ready to go beyond small talk—maybe with a friend or after a good chat—these questions help you get closer.

  • “If you were a character in a movie or book, who’d you be?”
    So fun—it shows how they see themselves and can lead to a great chat about movies or stories.
  • “What did you want to be as a kid? Still chasing any of that?”
    Connects their childhood dreams to today, giving you a glimpse into their life.
  • “What’s something that scares you deep down?”
    A big one, but it can spark real, honest moments if the vibe feels right.
  • “Any regrets that stick with you?”
    Use this carefully—it’s a deep dive into their past, but it builds trust.
  • “Who’s someone you really admire?”
    Great after mentioning someone inspiring—it shows what matters to them.

Fun Starters for Holidays & Events

These tie into special occasions or events, making your chats feel fresh and timely.

  • January: “Got a New Year’s goal you’re excited about?”
  • February: “You into Valentine’s Day, or is it just a big gimmick?”
  • March: “Any fun St. Patrick’s Day plans?”
  • April: “When did you stop believing in the Easter Bunny?”
  • July: “Best fireworks show you’ve ever seen?”
  • October: “What’s your favorite Halloween costume ever?”
  • November: “What’s the one Thanksgiving food you need on the table?”
  • December: “How do you and your family do the holidays?”

For birthdays:

  • To the birthday person: “What’s the best thing from this past year?” or “What’s your big hope for the year ahead?”
  • To everyone else: “What’s the best or worst birthday gift you’ve ever gotten?”

Tips to Make These Work

  • Be Real: Don’t be shy about trying deeper questions if the moment feels right—it makes the chat memorable.
  • Share Your Answer: If they’re stuck, toss in your own response to make them feel at ease.
  • Use What’s Around You: The food, the music, the event—lean into the setting for natural starters.
  • Listen Well: Follow up on what they say to keep things flowing and show you care.

Try these out next time you’re at a party, a work thing, or just chatting with someone new. You’ll be amazed at how quickly the conversation lights up! Want more ideas? Check out Science of People for some cool tips, or poke around X to see what others are saying about connecting with people.

FAQ: Your Questions About Great Chats, Answered

What’s a super easy way to start talking to someone new?
Just say something like “Having a good time?” or comment on the setting, like “This place is so cool—you been here before?” It’s low-pressure and gets things going.

How do I avoid those awkward silences?
Ask something open-ended, like “What’s been the best part of your day?” or “Got any weekend plans?” It gives them plenty to talk about.

What if I’m nervous about asking deeper questions?
Start with easy stuff to warm up, then slide into something like “What did you want to be as a kid?” when you’re both comfy.

Can I use these in texts or video calls?
For sure! Questions like “What’s been the highlight of your week?” work great in a text or Zoom chat.

Where can I get more tips on talking to people?
Swing by Science of People’s free course for awesome ideas, or check X for what people are sharing about great conversations.