68 Killer Conversation Starters So You Can Start A Conversation With Anyone, Anytime

How can you have dazzling conversations with everyone you meet? I have a few tips and tricks to using easy conversation starters that lead to amazing and memorable conversations. 

A good conversation starter topic can make a normal conversation great. I have broken down this post into different types of conversational situations you might find yourself in. These conversation starters can help spark interesting, deep, and memorable conversations with anyone.

And while you’re at it, take this free goodie on the go to level up your self-improvement skills:

Conversation Starters for Any Situation

Let’s start with some killer conversation openers. These are great for simply opening a conversation with someone new or someone you haven’t seen in a while. And they’re far more interesting than the standard “Where are you from?” and “what do you do?” those are so boring. Try these instead.

1. Working on anything exciting recently? 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 favorite hobby, they can. If they want to tell you about their job, they can. And it’s a great way to know what’s at the top of someone’s mind.
2. What was the highlight of your day so far? This is my alternative to “How are you?” Asking someone the best part of their day is a great way to bring up positive vibes, as opposed to just giving you a boring update.
3. What’s your story? This is an interesting conversation starter because it invites someone to tell you a story about them, and you never know what exciting thing they might tell you.
4. 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.
5. How do you know the host? This one can be modified to any kind of event. If you are at a party, hopefully you both have the host in common. If you are at a networking or work event, you can modify it to “How long have you been a part of this organization?”
6. What was the highlight of your day today? This is a nice alternative to asking “how are you?” and it gets more interesting answers.
7. What was the highlight of your week? This is a great one to ask instead of the standard question “How are you?” or “How’s it going?” It helps people share a positive story instead of just giving an autopilot answer of “Fine” or “Good.”
8. Have you been to an event like this before? This one can be modified for most types of events, from birthday parties (did you come last year?) to networking events (do you come every month?).
9. What was the high-point and low-point of your day so far? This one is great if you have a talker. If you are speaking with an extrovert, asking questions for them to ruminate and expand on will tickle their fancy. Extroverts love this question.
10. 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 busy-ness can hook them in.
11.  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 they are looking at. Ask them if the food is good. These are very easy openers.
12. Having fun? A really easy cold approach opener is to look for someone who is by themself, but looks like they are 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 nicer opener than just “How are you?”

Keep the Conversation Going

Okay, those are my twelve killer openers. How about getting more personal? My next set of conversation starters are to help you continue the conversation.

13. What are you doing this weekend? Ever had that awkward lull in a conversation? This conversation starter is always welcome. And, if it is a Monday or Tuesday, you can modify it to ask “Did you do anything fun this past weekend?” Sometimes, I also try “What’s your favorite thing to do on the weekends?”
14. 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 are new to a city, you can talk about where they came from. Win-win!
15. Keeping up with __sport / tv show / news__ recently? If you are 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!
16. Can you recommend any unique cocktails / appetizers / desserts here? 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.
17. All the food looks so good… I’m not sure what to get! What are you thinking? Or what have you tried? A variation of asking for a recommendation is asking simply for advice on what to order. Even at networking events, you can walk up to the bar to get recommendations.
18. 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 are in a house, a restaurant, or a ballroom, there is always something unique to comment on and ask about.
19. Did you see that viral ____ YouTube video? It was all over my social media today. If there is a great video you just watched, bring it up. If they have seen it you can laugh together. If they haven’t, you can show them!
20. I’m making a coffee / going to grab a drink, does anyone else want one? This one is fantastic because you can use this to address an entire group–maybe your new team on your first day at a new job, or a group of people you are sitting with for a presentation at a conference. This can be a good way to test the water and open up further conversation with the people who join you on your coffee run.

When in doubt, if you feel a little awkward asking personal questions right out of the gate, use your environment and surroundings to create conversation. Comment on the food and drinks. Ask about the venue or location. You also can ask general interest questions, such as their favorite sports team or YouTube video.

Take Your Conversation to a Deeper Level

Now let’s get to the deep conversation starters.

Let’s say you have been speaking to someone for a while, or it is a friend you have seen many times before and you need MORE to talk about. These are my deep conversation starters. In my book Captivate, I break down every interaction into 3 phases. The first 5 minutes — this is during your first impression when you are getting to know someone. The first 5 hours — this is when you start meeting for coffee, working together, or going on dates. And last, the first 5 days –that’s when you truly find friends, partners, and long time colleagues. These questions will help transition you from the first 5 hours to the first 5 days.

21. 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 great 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.
22. When you were growing up, what was your dream job? Is any part of that still true? I love asking this one anytime someone has just mentioned something about their childhood or growing up. It also helps you talk about whether their current job is similar to their original dream.
23. What’s your biggest fear? Whew, this one is deep, but soooo good! It always sparks great conversation.
24. What’s your biggest regret? Talking about regret can really help you get to know someone and their past. Only ask this if you really want to get to know someone!
25. Who is your role model? If you are talking about an inspiring person, a boss, an author, or even a celebrity, you might be able to ask the person about their role model. This is a great way to talk about who inspires you too!

Remember: Be bold. Ask the deep stuff. If you are not real, the majority of conversations can hover on the surface-level topics. It’s refreshing to talk about more meaningful areas of our lives. It’s true, some of those conversation starters may be a bit forward, but if the conversation is progressing well, I encourage you to try them. You never know what you will find out!

Conversation Starters for Work Appropriate Topics

The most successful professionals know how to both be productive at work and be likable. How can you do this? You have to use the right conversation starters to open genuine, authentic conversations in the office. I love all of the conversation starters I have already mentioned for trying with your office colleagues, but here are a few more.

26. Is there a charitable cause you support? Sometimes at work all you talk about is… well… work. This question is great to learn what someone is passionate about outside of work. Make sure you have your favorite charity picked out before you ask so you have a great answer too!
27. I’m a bit nervous about the _____. Have you ever done it before? Sharing personal information to others can increase how likable you are perceived to be, and can help form new social bonds. You can use this trick to start a conversation at work with a colleague, and get some good advice on whatever challenge you’re currently facing–whether it’s a new piece of software or a difficult client.
28. What has been the best thing about working here? This is especially helpful if you are starting a new job. You can also use this one if someone new has joined the team and you want to share your favorite thing with them.

Have you learned any insider tips about working here? You never know what you are going to hear with this conversation starter! It’s a good one! I love to ask for insider tips and insider knowledge.

Conversation Starters for a First Date

So you’ve ordered your drink and found a nice table. You know how to flirt, but do you know what to talk about on a first date? The best conversation starters for dating are ones that can give both of you an insight into the other’s personality and life.

30. What job did you want to do when you were a kid? Maybe they wanted to be an astronaut, or a vet. You can ask follow up questions too. Are they still interested in space studies? What changed when they grew up. Do they love the job they are in now? This type of conversation starter can open up topics such as future goals and professional development too.
31. If you had to pick one–skydiving, bungee jumping, or scuba diving–which would you do? This first date question is great to figure out if your date is an adventurer. It might turn out that they have done one or more of these things already. Or, they might be terrified of the idea of any of them. And if you are adventurous, good news: adventurous people are usually considered more attractive. Either way, you’re bound to get a great answer and an insight into the way they approach risk.
32. What’s the most important thing I should know about you? On a first date, you are trying to really get to know each other. Basically, you are trying to suss out if someone would be a great fit for you (and you for them). This question is a great way to get to the heart of the matter.
33. When you were a kid, what did you think your life would look like now? The ideal conversation starter for a first date is a Trojan Horse –something light and whimsical–and,actually, it’s a good excuse for you to share your aspirations with your date and open up potential conversations about your childhoods, education, or hobbies.
34. Which of your family members are you most like? Are they particularly close to their mom, their dad, their great aunt? This question gives you an idea of their family setting, and also gives them an easy opportunity to describe themselves simply. They might say they are most like their godfather because they love books, or like their brother because they have a crude sense of humor. Their relationships with key people in their lives is likely to give you some insight into how their relationship might look like with you.

There are so many great conversation starters that can be used on a date. We even have a dedicated post on first date questions if you need even more ammo!

Conversation Starters for Kids

“Sure, I don’t mind babysitting for the night.” The words kind of slip out before you can think it through, and you’re left with a kid you don’t know. Is Batman still cool? Are Dinosaurs? Is it even still cool to say cool?

Don’t worry, we’ve got you. With these great conversation starters with kids, you’ll never run out of discussion topics. If it feels awkward, remember that research suggests back and forth conversations with children helps boost their brain development.

35. Do you think there are aliens on other planets? This one is fun and there is no wrong answer; either way, the conversation will be great. If they say no, ask them why; if they say yes, ask them to think about what life on another planet might look like. Kids’ answers are usually surprisingly profound and creative.
36. If you were an animal, what animal would you be? Why? This is an easy way for a child to tell you about their personality. They might relate to a puppy because they’re playful and run around a lot, or a fish because they love swimming. Also consider, what would you be? They’ll probably ask you back, so make sure you have a good answer.
37. When you’re a grown up, what type of house will you live in? This is a more exciting take than the “what do you want to be when you grow up?” question. Loads of adults will ask that–b o r i n g. Instead, ask about what their house will look like. Do they want a swimming pool, a garden full of jungle plants, a slide from their bedroom into the living room? Encourage them to get creative. It might give you some fun home decor tips too.
38. Who would win in a fight, a robot or a dinosaur? You can take cues from things around you–do they have some toys in the room, or a superhero on their shirt? Use this to form a question, the sillier the better. You’ll make them laugh, and they’ll rate you as the coolest grown up.

Funny Conversation Starters

Funny conversation starters can be used in (almost) all of the situations above and they serve only one purpose: to make people laugh.

Laughter is important for bringing people together, so you’re sure to be the life of the party with one of these funny conversation starters.

39. What was your worst fashion disaster? Everyone has a few outfits from their past that seemed like a good idea at the time. This conversation starter will help you get to know what the people in your life were like before you met them. It will probably come with a few great stories about their days as an early 2000s emo or 1960s mod. What makes this funny conversation starter especially useful is it can cross the age divide, bringing older members of the party into center stage with fashion faux pas from the past.
40. What’s the most embarrassing thing you did at school / when you were a kid? This conversation starter works best in groups, when people will have time to think of their own story while laughing at the others sharing theirs. Reminiscing about the past can make people feel calmer (so it may be worth cracking open this conversation starter on a tough day at the office).
41. If you had a reality TV show about your life, what would your theme song be? It’s a good way of talking about music without asking people what bands they like (which can be a bit stilted and boring), and it short-circuits any indier-than-thou posturing in the name of fun. Bring it to life in the style of a ‘90s sitcom by probing people on the cheesy clips that might accompany their montage bonus points if you get your friends to suggest your theme tune).
42. What’s your plan if there was a zombie apocalypse? Honestly, you’ll be surprised by the amount of detail people can go into it while describing their remote getaway or elaborate escape routes. This funny conversation starter can turn raucous as you pick holes in each other’s doomsday survival plans.

It might sound counterintuitive, but despite learning some great conversation starters, keep it relaxed and natural. Keep these ideas somewhere in the back of your head for lulls in conversation and awkward silences; don’t try to crowbar them into a conversation that is naturally flowing in a difficult direction. Just be yourself, have a genuine interest in people and their lives, and try to learn about them.

Calendar Specific Conversation Starters

You can also use time to help you think of great conversation starters. These are really helpful to have in your back pocket. Whenever there is an upcoming holiday or special event, I use these as a basis for fun and light-hearted conversations. Here is a calendar-inspired conversation starter list for you. Remember you can be creative with these as well. If there is ANY holiday or event coming up, be sure to ask about it!

43. January: What’s your New Year’s Resolution?
44. February: Do you usually celebrate Valentine’s Day? Do you think it is a real or fake holiday?
45. March: “I went to the coolest Irish bar last St. Patrick’s Day. Doing anything fun this year for it?”
46. April: How long did you believe in the Easter Bunny?
47. July: What’s the best fireworks display you’ve seen on the 4th of July?
48. October: What’s the best Halloween costume you ever had? Or Do you like haunted houses or scary rides?
49. November: What’s your favorite Thanksgiving Dinner food?
50. December: How does your family celebrate the holidays?

Birthday Party Conversation Starters

If you have a birthday or are celebrating someone else’s birthday, I always ask these to get the conversation going:

51. To the birthday person: “What was the highlight of your last year?” Or, “What do you want to achieve for next year?”
52. To fellow celebrators: “How do you usually celebrate your birthday?” Or, “What was the best birthday you ever had?”
53. To everyone else: “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.

Tinder, Bumble and Other Dating Conversation Starters

Tinder can be a challenge to having deep conversations — but it can be done! The best conversation starters on Tinder or other dating apps isn’t always a cheesy pick-up line. Instead, you want an opener that works twofold. You want to communicate that you have taken the time to read their profile and learned something about them, and also to tell the other person something about yourself. It’s a win-win, and the conversation will flow naturally from there once you have found some common ground.

Choose one of these great conversation starters to open a conversation on Tinder, and modify it to show your own personality. You just have to fill in the blank:

54. You have a ___? Me too! Tell me more. Anything you have that is similar to the person you are interested in is a great conversation starter on Tinder. We like people like us. This is known as the similarity-attraction effect. Fill in the blank with your similarity, and then ask for more details.
55. Hey – you’re a _______? That sounds really interesting. What’s your favorite thing about your job? People love talking about themselves. Keep this in mind when you’re starting conversations online too. People are more likely to respond to you if you ask a question. It goes without saying, but modify this conversation starter depending on their profile.
56. Sorry if this is a bit forward, but I’m going to try out that new _____ that opens downtown next week–would you like to come?  Straight to the point, this conversation opener makes it clear that you’re interested in a genuine relationship and would like to meet in real life. Make sure to keep your language casual and friendly, and you’ll ace it.
57. Hey, how is your week / weekend going? This one is nice and simple, but can open a conversation to a lot of different directions–perhaps they’ve had a weekend stuck in the office working, or they’ve had an amazing week of sales. It’s important to give them some information to reply to, too.

Icebreaker Conversation Starters

Let’s dive into some fantastic icebreaker conversation starters that can turn mundane interactions into exciting and engaging conversations:

58. Tell me about you: This opener invites the other person to share something meaningful about themselves. Whether it’s their job, their hobbies, or their family, it’s a great way to discover what’s on their mind.
59. Working on anything exciting lately? Instead of the typical “What do you do?” question, ask if they’ve been working on something thrilling. It encourages them to share positive aspects of their life.
60. What’s your story? This intriguing question prompts the other person to narrate a unique story about themselves, opening the door to unexpected and captivating conversations.
61. What personal passion project are you working on right now? Delve into their personal interests and discover if they have any exciting side projects or hidden talents.
62. How do you know the host? This versatile question can be tailored to various events. It’s a great way to connect at parties or networking gatherings by exploring your mutual connection.
63. What was the highlight of your day today? Instead of the typical “How are you?” question, inquire about the best part of their day, leading to more interesting and positive answers.
64. What was the highlight of your week? Elevate your conversation by asking about their weekly highlights, encouraging them to share memorable experiences.
65. Have you been to an event like this before? Adapt this question to the specific event you’re attending, whether it’s a birthday party or a networking event. It’s an excellent way to initiate conversations and find common ground.
66. What was the high-point and low-point of your day so far? If you’re talking to an extrovert who enjoys elaborating on their thoughts, this question can lead to lively discussions and deeper insights.
67. Has this been a busy time for you? Use this conversation starter if you sense that someone is distracted or not fully engaged. Acknowledging their busy schedule can help re-engage them in the conversation.
68. How’s that drink/appetizer/artwork/game? Incorporate your surroundings into the conversation by asking about whatever the other person is currently enjoying, be it food, drinks, or the environment.

BONUS: How to Master Small Talk

Are you bored of the following questions:

• “How are you?”
• “How’s the weather?”
• “The traffic here was pretty bad, huh?”

I used to dread getting these questions. But fear not! I now LOVE getting asked these normal conversation starters, all because I found one AMAZING trick to change them from boring to magical! Watch my video below to find out how:

Any and all of these conversation starters 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 conversation anyway! 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.