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. Check out this video on the art (and science) of sparkling conversation and learn my 33 favorite killer conversation starters:
How about good conversation starter topics? I have some awesome conversation starters that can help spark interesting, deep and memorable conversation with anyone you speak with:
Let’s start with some killer 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. 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.
2. Working on anything exciting lately? 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.
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?
7. What was the highlight of your week? Are great ones to ask instead of the standard questions such as “How are you?” or “How’s it going?” It also helps people share a positive story instead of just 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 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 themselves, 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?”
Continue the Conversation:
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 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!
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.
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 coffees, working together or going on dates. And lastly, 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.
20. 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.
21. 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 if their current job is similar to their original dream.
22. What’s your biggest fear? Whew this one is deep, but soooo good! It always sparks great conversation.
23. 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!
24. 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 our conversations can hover on the surface-level topics. It’s refreshing to talk about more meaningful areas of our lives. Its 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!
Event Specific Conversation Starters:
My last set of conversation starters are all timing specific. These are actually really helpful to have in your back pocket. Whenever there is an upcoming holiday or special event, I use these as a base 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!
January: What’s your New Year’s Resolution?
February: Do you usually celebrate Valentine’s Day? Do you think it is a real or fake holiday?
March: “I went to the coolest Irish bar last St. Patrick’s Day. Doing anything fun this year for it?”
April: How long did you believe in the Easter Bunny?
July: What’s the best fireworks display you’ve seen on the 4th of July?
October: What’s the best Halloween costume you ever had? Or Do you like haunted houses or scary rides?
November: What’s your favorite Thanksgiving dinner food?
December: How does your family celebrate for the holidays?
And lastly, if you have a birthday or are celebrating someone else’s birthday, I always ask these to get the conversation going:
To the birthday person: What was the highlight of your last year? Or What do you want to achieve for next year?
To fellow 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.
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.