Great Conversation Starter Questions

When Edwin and I moved to Charleston, we knew almost no one here. Now, 2.5 years later, we have so many incredible friends that I can’t imagine not knowing! How did we do it? We put ourselves out there A TON. I remember a time when I wondered if we’d ever get to a point where we broke through, formed lasting friendships, and would run into friends at parties and around town. Looking back, I think that phase is necessary to making new friends because it’s motivation to get out and about.

Needless to say, I’ve been wanting to write a post like this for awhile. This past holiday season gave me the motivation I needed because the holidays were so busy with parties and social gatherings. It can be difficult to walk into a party and strike up a conversation with someone you don’t know. So, I’m sharing great conversation starter questions to help make your conversations better. This applies to people you know and to people you’ve only just met! Knowing a mix of conversation starter questions is a great tool to have up your sleeve!

P.S. How cute is Allison’s baby bump in these photos?! I can’t wait to be the baby’s unofficial Aunt Jilly!

Great Conversation Starter Questions

Here is a breakdown of my ideas for great conversation starter questions! I’m sharing exactly what to ask and why these questions will bring you lively and successful conversations at your next social event.

Tell Me About You.

Haha yes I’m aware that my first suggestion is a sentence instead of a question but it’s an important one so I’m running with it. If you’re chatting with someone you’ve just met, asking the person to tell you about them is so much better than asking “How are you?” Trust me! “Tell me about you” Lets the person know that you are taking an interest in them and it gives them the opportunity to pick and choose what they want to share. Everyone feels comfortable as there won’t be any awkward sentences. I promise, conversation will flow easily from here!

How Do You Know The Host Or Hostess?

Bingo! If you’re at a party and you ask someone how he/she knows the host/hostess, then you’re immediately establishing common ground over a person you both know. It is an easy conversation topic if your mind goes blank and you want to get the ball rolling!

How Did You Get Connected To This Group/Event?

Think strategically about the event you are attending. Is it a work conference or networking event? Is it a book club or recipe swap? Or Is it a charity organization meeting or volunteer opportunity? When striking up a conversation at such an event or gathering, ask the person you’re talking to what their connection is to the group/event.

Catch Me Up On Your Life Since The Last Time I Saw You.

Our lives are so fast paced that it can be challenging enough to keep up with our own lives all the time, let alone the lives of everyone we know. Sometimes I find myself checking social media before I reconnect with someone just to make sure I didn’t miss a major life event (an example would be, did they get engaged over a trip and I somehow missed it? Or did they start a new job?). Saying to someone, “Catch me up on your life since the last time I saw you” allows the person to share any life changes or milestones without either person feeling out of the loop or not appreciated.

What Keeps You Busy Outside Of Work?

Have you ever worked a long day or week only to go out and get asked about work? It’s probably the last thing you want to talk about. Disconnecting is healthy! As such, I suggest asking someone what keeps them busy outside of work. If it is a new acquaintance, this allows the person to share if he/she has kids, is involved with any group or sport they love etc. If it is a friend you are establishing more of a relationship with, it will help you both discover common interests. Either way, you will learn a lot quickly!

What Is The Highlight Of Your Week So Far?

One of my friend’s husbands asked me this recently at a dinner party and it stopped me in my tracks because I thought, “what a great question!” It was one of the best opener questions I’ve ever received. Asking someone what the highlight of their week is sets the conversation in a positive direction and is so much more thought provoking than asking someone how they are. I wouldn’t necessarily classify “what is the highlight of your week” in a category of deep conversation starters but it is certainly interesting! You will get whoever you are talking to to reflect on something that brought them happiness, which I guarantee will make them associate your conversation with happiness.

What Is Something Not Many People Know About You?

This is a fun question to ask because it makes people realize you are taking an interest in striking up a conversation with them. You’ll learn a colorful, surprising, or off the beaten path fact about someone, which is always fun! An example of how I would answer this question would be revealing that I am scuba certified. Now the conversation is opened up to traveling, beach vacations, outdoor activities/sports etc. It gives people a chance to be lighthearted too, which is great when people are “on” at social gatherings. People can reveal silly things like their guilty pleasure tv show!

Do You Have Any Upcoming Trips This Year?

Who doesn’t love to travel? Usually, travel is a great source of excitement so conversation flows really easily when you ask about a happy topic like travel. It is a personal question (without being too personal) that will help bridge small talk into a conversation where you can hopefully find things in common like your bucket list travel destinations.

I Need To Step It Up In The Kitchen. Have You Tried Any New Recipes Lately?

This is an easy question to ask anyone. Chances are everyone has a go-to recipe they love or something they’ve been wanting to try that they can talk about. If you happen to ask this question to someone who reveals that they aren’t much of a chef, then you can transition the conversation to talking about restaurants…

Have You Been To A Restaurant Lately I Need To Know About?

The topic of restaurants is a super easy topic to dive into that can keep people talking forever. Everyone has a favorite restaurant or, thanks to social media, somewhere they are dying to try. If all else fails, talk about restaurants!

I’m Looking For A New TV Show To Watch. Have You Watched Any Great Shows Recently?

I honestly think I learn about a new TV show every single week! There is so much to watch and, as such, talk about. I like this conversation starter because everyone in the conversation is bound to walk away with new knowledge and new recommendations. It’s a win win for everyone!

I’m Looking For A New Book To Read. Have You Read Any Great Books Recently?

Similarly to the TV show question, this is an easy topic because there are always books coming out. So, if you find someone to chat with who loves books, then you can talk for hours! Be sure to not only give your book recommendations but to also ask for the recommendations of whoever you are talking with.

How To Make Conversations Better

Don’t Fret Over the Perfect Opening Line

There is no such thing as the perfect conversation opener. It’s also pretty impossible to always crack funny conversation starters. So, don’t fret about it! Chances are if you go for a perfect one liner, then it will fall flat or come out awkwardly. When meeting new people, reference my list above in this post for some helpful and good conversation starter ideas.

Take Cues From What You Already Know

I find this tip so helpful! This applies when talking to a brand new person or someone you’re actually getting to know well. If you’re talking to a new person at a work event or party, then chances are you work in the same industry or have at least one friend in common (the host). Use this information to keep a conversation flowing. If you’re getting to know someone better, then use what you know from past get-togethers to fuel the conversation this time around. Ask about something they mentioned last time you saw each other – a trip, a work project, a house project, a date, a child’s birthday… whatever!

Feel Free To Offer Your Opinion If Your Give The Other Person The Chance To Offer Their Opinion Too

When chatting with someone or starting a conversation about a new topic, either ask the person “What do you think about X?” or state your opinion and immediately follow it up with “What do you think about it?” As long as you’re asking the other person what their opinion is, then providing your opinion shouldn’t hurt or stunt the conversation. In fact, it will lead to interesting conversation of similar or differing opinions!

Practice Active Listening

What’s active listening? Active listening is showing someone that you are an engaged member of the conversation even when not in the lead of the conversation. Practice active listening by offering verbal and physical cues. A verbal cue is a question as simple as “what happened next?” or a statement as simple as “that must have been a surprise.” Positive physical cues are things like smiling, making eye contact, and avoiding crossing your arms. People love feeling like they are being heard so being an active listener is key for great conversations!

Avoid Interrupting

Absolutely no one likes being interrupted. I have such livid memories of growing up and my parents reminding us of this all the time! For many (including me!), not interrupting is a life skill that can be practiced for the rest of your life. When people feel like they are being listened to and aren’t being interrupted by you, they will respect you more.

On Jillian: Sweater (old – similar, similar, similar) / Jeans / Booties

On Allison: Sweater (old – similar) / Jeans / Purse / Booties (old – similar, similar)

Get our Great Conversation Starter Questions Look:

Photography by Edwin Eversole