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
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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.
Anshu Pathak is a passionate writer and avid reader whose love for stories shapes her world. With a heart full of imagination, she weaves tales that resonate with emotion and depth. When she’s not crafting her next piece, you can find her lost in the pages of a novel, exploring new worlds and perspectives. At Moodframe Space, Anshu shares her creative journey, offering insights, stories, and reflections that inspire and connect with readers everywhere.