What First Date Questions Should You Ask To Break The Ice?

Keep these first date questions in your back pocket for your next night out.

So you've met (or swiped right), expressed mutual interest to go on a first date, agreed on a time and place, and got yourself there. Now what? 

A good first date relies on good conversation, but if you get nervous meeting someone new — and who doesn't? — saying anything after "Hi" can seem more like an uphill climb than scaling Mount Everest. Even your best first date ideas can't help you if you're suddenly tongue-tied and don't know what to say.  

While most people always know what to say around family, in the office, and out with friends, they often don't know what to talk about on a first date. That's when keeping a few first date questions in your back pocket saves the day, er, date. 

Not only will they help you break the ice, but with a little luck, they may even help you meet the love of your life. 


So in the spirit of the classic game "20 Questions," here are 20 first date questions to ask anyone, (almost) anywhere. 

1. What’s your go-to drink?

This question can easily jumpstart any first date conversation as you'll most likely be choosing a drink — whether it's a cocktail, coffee, or simply water — as soon as you settle in. Their answer will not only tell you their taste preferences, but can lead them into sharing some clues into their overall lifestyle. For example, someone who says "a craft beer" may also mention how they spend their weekends checking out independent breweries. If you're into that, a second date could be in order. 

2. Did you always want to do what you do now?

This question goes beyond the run-of-the-mill "What do you do?" (Though if you don't already know, you should probably get that out of the way first.) Instead of asking them about their day-to-day work duties, which isn't that much fun to talk about, especially if you just finished doing them, this question stirs the conversation toward your date's passion that led them to their current position. Even if they answer "no," you can still learn about their career path and their ambition for the future. 

3. What do you usually do on the weekend?

This is one of the most straightforward ways to figure out if your personalities and lifestyles will match enough to consider a long-term relationship. After all, if your date spends every weekend waking up early to go rock climbing, and you prefer lazy mornings with a good book, you might not be a perfect fit. On the other hand, this could be great news if you enjoy your alone time and want to remain independent while with a partner. 

4. If you could live in any television show, which would it be?

Not only does this question lead into a conversation comparing pop culture tastes, but it also can give you a preview into what you can expect on a "Netflix and chill" night. While this topic seems light and fun, people's tastes in television shows are often a reflection of the stories they believe are worth telling and, consequently, their values. Seriously, what you decide to binge-watch during cuffing season is no joke. 

5. What’s your favorite thing about your best friend?

This question is a casually sneaky way of finding out what qualities your date values most in the people closest to them. Their answer will help you figure out if you're compatible based on your possession of that quality and/or how you value that quality in friends, as well. It's also important to ask because many couples eventually consider each other best friends, along with the ones they had before getting together. If you like their answer, you can even follow it up with, "Your friend sounds awesome. How did you meet him/her/them?" 

6. If there was an Olympics for everyday activities, what activity would you have a good chance at winning a medal in?

Voilà — another light and fun question that sneakily shows the inner workings of your date's personality. Not only will you learn what they're good at, but you'll also learn what they take pride in. That's a great, but ridiculously easy, way to find out the way your date expresses their core values on a daily basis. And if you're lucky, they'll say "cooking," so you know a great meal could be in your future, served with even better company. 

7. What's the last book you read?

Notable author and filmmaker John Waters is known for saying, "If you go home with somebody, and they don't have books, don't fuck 'em!" While you might not fully subscribe to that life motto, asking your date about their taste in literature is important if you're looking for an intellectual equal. Even if you're not, it's another way to learn about their story preferences and values. Of course, if they can't remember their last book, we'd let it slide if they're an online article aficionado instead. 

8. Where did you go on your last vacation, and would you go back?

This question will tell you whether your date is a beach or mountains, active or leisurely, and even domestic or international traveler. Better yet — if you've also been to the place they mention, that'll spark an instant conversation where you can share and compare experiences. You can also use this question to jumpstart a conversation about future travel destinations, just don't start planning that epic couples' vacation just yet ...

9. What are people often surprised to learn about you?

People often love talking about themselves, and even if your date doesn't, this can be a fun way to get them out of their shell. After all, many people don't feel 100 percent themselves on first dates, so this can be a way to break the ice. This question gives your date the opportunity to share a special skill or their best-kept secret, forging an instant bond with you. But fair warning: If you ask this question, you should prepare yourself with an answer to trade.

10. What’s your favorite app on your phone?

So long as they don't say a dating app, this should be a fun question that also tells you how your date spends a fair amount of their free time. If they're obsessed with Candy Crush, you know they've got a competitive spirit. If it's Snapchat, then you can probably expect to see your fair share of selfies if the date goes well. 

11. Are you into social media?

Just like the first date question about app usage, asking about your date's social media habits will clue you in on their priorities, and, more importantly, if they're compatible with yours. Whether they post to Instagram once a day or once every six months, their answer will tell you what kind of person they are and what you can expect from an Instagram-official relationship with them.

12. What's your guilty pleasure?

Everyone has one, but not everyone just comes out and admits it. Asking your date about their guilty pleasure will (gently) force them to share a potentially embarrassing side of themselves, revealing the real person underneath the first-date version. And who knows? If you're really lucky, you might share the same guilty pleasure, which you can now enjoy together. 

13. Do you have a favorite childhood toy? If so, where is it now?

This question isn't so much about the toy itself, but about the story behind it. Who gave it to them? When did they get it? Why did they love it? This can even give you some insight into how they were raised, which is important as people's relationships (or lack thereof) with their parents can influence their romantic relationships. 

14. Do you have any siblings?

On the topic of family, one way to learn about your date's relationships with the people they're biologically closest to is to ask about their siblings. If they have a few siblings, they might talk about the fun of being raised in a big family. If they're an only child, they might mention a close cousin or an unbreakable bond with a parent. Regardless of their answer, you'll probably also learn about their general perspective on families and can see how it compares to yours.  

15. What’s the worst movie you’ve ever seen?

As important as it is to learn what a potential partner loves in pop culture, it's just as necessary to learn what they can't stand. Again, this can help you figure out if your interests are compatible ... and just make sure they don't happen to hate your favorite movie. (Cuffing season is serious business, people!) Not only does this keep the conversation fun, but you might even get a so-bad-it's-good recommendation out of it. 

16. If you had to choose between a job you loved that didn't pay very much and a job you hated but paid extremely well, which would you choose?

OK so full disclosure, I was once asked this on a first date, and it took me about two seconds into the ensuing discussion with my date to realize we weren't compatible. How? This question gets to the core of each person's idea of what creates the most happiness: emotional fulfillment vs. financial security. While opposites can — and certainly do — attract, it's good to know that sooner rather than later. 

17. Is there a special place you visit regularly?

Whether it's a hidden spot in their hometown or a favorite restaurant, this question will tell you a lot about who your date is when nobody else is looking. That's important because that's the person you actually want to meet. Encourage them to share what exactly makes that place so special and why they return to it. If your first date goes well, you might end up seeing it yourself someday.  

18. When you were a kid, what seemed like the best thing about being a grown up?

This question is great because it allows you and your date to laugh about all the things you misunderstood as children, as well as remember the good ole days of mandatory naps and designated snack times. You can even take this question further by flipping it on its head and asking your date about the one thing they did as a child that they wish they could still do now. 

19. What made you ask me out (or accept my invitation)?

Only ask this question if things are going well and you're 99 percent sure a second date is in sight. This question is a bit meta, but that's also why it's important to ask. Your date's answer will not only tell you what they value in a romantic partner, but the potential they see in you to become that partner. Even if your romance fizzles out after a while, their positive perception of you can serve as a helpful reminder of your awesomeness whenever you need a little confidence boost — perhaps before your next first date? 

20. If you could give everyone just one piece of advice, what would it be?

Mine? "Dating sucks up until the very last millisecond that it doesn't." So the next time you're on another first date (now equipped with these questions, of course), keep that in mind. There's a light at the end of the tunnel; you just don't know how long that tunnel is. The only way out is through, and these first date questions will hopefully make your time on the dating scene a great one.

Cover image via  Dragon Images / Shutterstock


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