15 Non-Awkward Ways To Break The Ice On A First Date

Because good conversation starters are like the secret sauce of getting to a second date.

by Natalia Lusinski and Kristine Fellizar
Originally Published: 
Break the ice on a first date by asking about their bucket list.
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In this day and age, when you tell a friend you’re going out on a first date, there's a good chance it's with someone you met online. Although you and this person have likely messaged back-and-forth — and maybe even had a FaceTime sesh or two — nothing is guaranteed. You’ll still need to see if that same chemistry you had online is there in person. Even if you feel like you already know someone, you’re technically meeting them for the first time. So how do you break the ice on a first date with someone you’ve never met in person before?

Dating and relationship coach, Varsha Mathur, tells Bustle to start with a light topic. “Be interested in them and ask questions about the light-hearted stuff, such as how they got into the city or where they found parking,” Mathur says. “Asking questions that require black and white answers are a great way to start deeper conversations.”

If it's an online date, make sure you take another look at their profile. “To ease the stress, it’s good to take a screenshot of your date’s profile and review it before you meet," Julie Spira, online dating expert and digital matchmaker, tells Bustle. "Believe it or not, some singles show up on dates, suffer a temporary loss in memory, and don’t remember their date’s name or what they look like.”

While this can be totally embarrassing, it can also signal to your date that you’re either a serial dater or one who doesn’t care much about the date you’re on. Reminding yourself about the specifics of the person you’re meeting — and what attracted you to them in the first place — will help naturally spark some conversation starters and ice breakers.

If you’re stumped on what to talk about on a first date — but don’t want the conversation to seem forced either — here are some icebreakers you can use.


Ask Them Something About Their Dating Profile

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If you met online, an easy go-to icebreaker is asking your date about something specific from their dating profile. “Being sincerely interested about something that caught your eye on their dating profile can show your date that you are intrigued and want to know more,” J.L. Kirkwood, certified relationship coach and author, tells Bustle. “If you are able to relate to something they’ve done, you get bonus points.”

He also suggests asking open-ended questions about their profile or something you discussed previously, like, “Tell me more about your love for hiking” or “What did you like most about your trip to Cancun that made you say you would love to live there?” “The secret sauce to ice breakers is creating a safe space for you both to open up, which will hopefully lead to a second date,” he says.

Spira agrees. “It’s great to have a fool-proof cheat-sheet of three specific questions to always ask on a date that relate to their profile,” she says. “Ask your date about a photo you liked, ask about their work if it’s listed, and ask about what it was like growing up in their hometown.”


Ask If They’re A Cat Person Or A Dog Person

It seems that many people are cat *or* dog people, not both. Well, now’s the time to find out which one your date is, David Bennett, counselor and relationship expert with Double Trust Dating, says. “I find that people love discussing pets, and it’s a great way to break the tension — because who doesn’t love discussing cuddly animals who purr, lick you, and walk on your face when you’re sleeping,” he tells Bustle. “It’s also a good way to get a conversation going, because it lends itself to a lot of follow-up questions about pet names, breeds, and even showing photos.”

He adds that it’s also a great way to see if any pet issues are potential deal-breakers for you, such as you being allergic to cats or that you can’t date someone who doesn’t like animals. “The cats-or-dogs question will get those out of the way,” Bennett says.


Ask About The Last Concert They Went To

Having similar taste in music can help you and a date bond, and if you ask them about the last concert they went to — or even the best concert they ever went to — it can help you learn more about them. “Remembering a fun time and sharing that with a new person is a great way to learn insight about a date,” says. “Then, allow their answer to lead into your story about your last concert — share what you liked about the music and whether you bought indoor or outdoor tickets, packed a cooler for a picnic, what you packed, etc.” She says to also make sure to ask follow-up questions, but don’t make it seem like an interview; instead, get to know about their experiences.


Ask Them What They’d Do If They Had The Day Off From Work Tomorrow

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Everyone spends their free time differently, and when you ask your date what they’d do with a spontaneous day off, you can learn a lot about them. “Now, depending on when it is in the week, their day might involve weekly errands and chores, catching up on a personal project (taxes, anyone?), or a weekend day-drinking with friends,” Thomas Edwards, dating expert and founder of The Professional Wingman, tells Bustle.

However, you can also ask them not to choose an answer like “errands.” “Overall, it’s a fun way to peek into your date’s day-to-day lifestyle,” Edwards says.


Ask Them Who Their Role Models Are, And Why

When you’re trying to break the ice with someone you’ve never met before, try asking about the important people in their life. For instance, many people have mentors and role models. According to Spira, asking your date about theirs can give you a glimpse into their character and being. “Whether it was a boss in a previous job, a mentor, or a relative, asking your date about their role model(s) lets you sit back and listen as someone talks about someone who’s meaningful in their life,” Spira says. “Plus, you’ll see how it carved out the foundation of who they are today.”


Ask Them What They Love So Much, They’d Do It For Free

A lot of people have passion projects that they do for free, whether it’s making music or volunteering for a cause. Asking your date what they do in their spare time or what they’d do for free, is a great way to learn about what really matters most to them. “This is so much fun because the answers are endless and likely silly, which allows vulnerability to come into play,” Edwards says. “For instance, you and your date can laugh about the ability to binge-watch a TV show in a day or work with Elon Musk on his next intergalactic mission. Whatever it is, it serves as a way to play fantasy a little bit, and you each get to reveal your fun sides.”


Ask Them About The Best Vacation They Ever Took

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Vacation stories are always a fun topic of conversation, especially if you’re looking for something to bond over. Many people have embarrassing stories, which you can exchange and laugh at together. Plus, everyone has a different vacation style — while some people are beach people, others prefer doing anything but lying in the sun all day. “Helping your date think about their fun vacations will put a smile on their face, and you’ll learn if they’re a sun worshipper, if they prefer to go museum-hopping in other cities, and so on,” Spira says. It’s a good way to check for lifestyle compatibility.


Ask Them About The Most Inspirational Thing They’ve Read Lately

With all the articles that fill our social media feeds and phones, asking your date what they’ve read lately — and what moved them — is a great icebreaker. “Find out what interests and inspires your date by asking about their last great read, whether it’s an article or a book,” Antonia Hall, psychologist and relationship expert, tells Bustle. When you’re meeting someone in person for the first time, it’s a good idea to keep the conversations positive. Talking about current events can be hit and miss. So, try sticking to conversation topics that are light.


Ask Them About Something They’re Wearing

What is your date wearing that stands out? A ring? A fun shirt? A cool hat? “All too often, people make the mistake of complimenting someone’s obvious physical good looks,” Carmelia Ray, online dating expert and dating coach, tells Bustle. “So stand out and compliment their style, their swagger, their shoes, earrings, jacket, or whatever really gave you a positive first impression."

Plus, then it will lead to other stories and questions, such as telling you about the flea market where they got the ring or how they went to every cool T-shirt shop in L.A. to track down this one vintage shirt — have you been to any of those shops?


Ask Them What’s On Their Bucket List

Everyone’s probably traveled at some point, whether it was road trips during their childhood or jetting to Europe after high school. But now, you can ask your date what *else* is on their travel list, too. “Whether someone has traveled, wants to, or doesn’t want to, it’s a simple way to find how cultured and worldly someone’s personality is,” Edwards says. “Their answer alone can trigger a whole new set of conversations to be had, now and in the future.”

Hall, too, believes asking your date where they’d like to travel makes for a great icebreaker. “Dream destinations can give you a great peek into someone’s lifestyle, goals, and is a good conversation-starter,” she says. “Plus, asking what’s on their bucket list will allow you to get to know the person better and to find out whether or not your interests align. Most people are happy to share their bucket lists, unless they don’t have one, which is another clue about them.”


Ask Them What They’d Do A Podcast About

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The whole point of a first date is getting to know someone better, and if you ask them, “If you hosted a podcast, what would it be about?” you’ll get a lot more insight into who they are, Bennett says. “I like this one because not only could some people say, ‘Well, I actually *have* a podcast’, which would score a lot of first-date ‘points,’ but it also can help you quickly discover what a person’s passions are without asking that question outright.”


Ask Them To Play “Two Truths And A Lie”

If you’ve never played Two Truths and a Lie, don’t worry — it’s easy; plus, you and your date will get to know a lot about each other. “Basically, you and your date have to say three things, but one of them has to be a lie,” Kirkwood says. “Leave it up to your date to figure out which one is the lie. Not only will this add some spice to your conversation, but it also allows you to get to know one another in a fun way.” He says that by doing something creative and fun, it’ll help loosen any tension while also bringing you two closer.


Ask Them To Do Something Interactive

There’s nothing wrong with getting dinner or drinks for a first date, especially if you barely know the person you’re with. However, dating expert and author, Kevin Darné, suggests going out for an activity like taking a cooking class, bowling, or going on a haunted house tour. “Almost everyone goes out to eat, have drinks, and sit across from one another for hours, but it's not too difficult to create a memorable first date these days,” Darné says. “The activity itself provides conversational engagement, especially if you are able to challenge each other in a fun way.” Bonus tip: If you’re the one choosing the place and activity, always choose something that makes you feel most comfortable, he says. That way, you can look good and may even teach your date a new thing or two.


Ask About The Craziest Thing They’ve Ever done

When in doubt, ask questions that can help bring out the fun side of your date. As Susan Trombetti, matchmaker and dating expert, tells Bustle, “Too often dates turn into jobs interviews, and job interviews you can make you nervous. Don’t get too serious. Just have light, fun conversations.” Asking a question like, “What’s the craziest thing you’ve ever done?” is a great one to get people talking.


Ask Them About Their Most Controversial Pop Culture Opinion

When you’re trying to connect with someone, opening with a pop culture question can be a good starter, especially if you know what they’re into from their dating profile. For example, “Were Ross and Rachel really on a break?” As Kate Maclean, resident dating expert for Plenty of Fish, tells Bustle, it’s one of the greatest debates of our time. “The answer to this question will tell a lot about a person,” Maclean says. “FYI:  According to 60 percent of singles, the answer is yes they were and no, Ross did not cheat!”

As you can see, you have several options when it comes to icebreakers to use on a first date with someone you’ve never met before. “Icebreakers are great to have in your back pocket to keep first-date conversation flowing, but they’re also a wonderful way to get to know the person better,” Hall says. “Just remember to match your questions with your own interests, and you’ll have nothing to worry about.”

Plus, the above will probably inspire you to think of even more first-date icebreakers, and the more, the merrier.


Varsha Mathur, dating and relationship coach

Julie Spira, online dating expert and digital matchmaker

David Bennett, counselor and relationship expert with Double Trust Dating

J.L. Kirkwood, certified relationship coach and author

Thomas Edwards, dating expert and founder of The Professional Wingman

Carmelia Ray, online dating expert and dating coach

Antonia Hall, psychologist and relationship expert

Kevin Darné, dating expert and author

Susan Trombetti, matchmaker and CEO of Exclusive Matchmaking

Kate Maclean, resident dating expert for Plenty of Fish

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