10 Questions To Ask On A First Date

You’re finally getting the chance to meet IRL with the person you’ve been eyeing on WhatsYourPrice. You can’t wait to see if you’re as compatible as you hoped. But you almost dread asking or getting asked the inevitable list of first-date questions:

“So, do you have any brothers or sisters?”

“Are you from here?”

“Where did you go to school?” 

Excuse us while we wipe the drool off our pillow. While there is nothing technically wrong with these questions, have you ever stopped to think about what you’re really learning about the person sitting across from you? Have those questions ever gotten you any closer to discovering your true compatibility before? Sure, they open up other topics that may snag you more of the deets you’re really looking for, but why sit through a barrage of boring Q&A? You’re certainly not boring, right?

WhatsYourPrice may be the shortcut to your dating goals, but we don’t stop after the introduction. We want to get you on first dates sooner and make them exciting. No, you don’t have to walk across hot coals or get matching tattoos to feel a rush on a first date. Good ol’ fashioned conversation can be the key to first-date success. 

We believe it’s time to redefine the usual litany of questions you’ve answered a billion times while trying to get to know your date. Go beyond What do you do for fun? and Where did you grow up? Instead, take a chance with questions that rarely get mentioned in first-date conversations. After all, a date isn’t an interrogation or an interview. It’s an opportunity to get to know someone you could potentially share more time and experiences with, and it should be FUN! 

Check out our top 10 unexpected questions to ask on your next first date: 

1. What did you do last weekend?

Not only does this question show interest in your potential partner, but it also gives insight into who they are beyond their WhatsYourPrice dating profile. Did they spend the weekend barbecuing with friends and family? Catching up on Netflix? Working? Playing video games until 3 a.m.? The key to this question is figuring out where you may be able to fit into their routine, and more importantly if they really even have one. For example, if you’re getting workaholic vibes or a sense that they are always busy, it may be a sign they aren’t ready for a committed relationship.

2. Where was your last vacation?

Although it might not sound too in-depth, this question actually provides even deeper intel than the first. Has your date not been on a vacation in years because they are too busy with work? Are they someone who prefers to stay home instead of traveling? Or do they make it a point to have an adventure in at least one new city, state, or country a year? 

We know you shouldn’t judge a book by its cover, but no one ever said anything about the inside of a passport. Listen carefully to your date’s answer as it lets you know if you’d be on the same page when it comes to your lifestyle. If they love to spend their vacations camping and you’d rather eat a rock than sleep on one, you may think twice about moving forward. 

3. What is one thing you hope to achieve in the next year?

This question goes beyond weekend or vacation plans and into hopes, dreams, and even passions. Maybe they’re an art buff who wants to see the Sistine Chapel in Italy or the Louvre Museum in Paris. Maybe they never knew their grandparents and want to travel to Scotland to visit the town their grandma grew up in. Maybe they’re an adrenaline seeker jonesing to spend a month trekking through New Zealand and conquering everything from bungee jumping off the Kawarau bridge to hiking Franz Josef Glacier. Or perhaps they are an aspiring author determined to write a novel to rival Stephen King. With this question, you may find shared interests, swap stories of boxes you’ve already checked off, or just learn something new. 

4. How do you feel about surprises?

We’re not just talking about people jumping out of cakes and yelling happy birthday, although that’s fun too. How your date deals with the unexpected can speak volumes about their personality, and whether you vibe with it. Can they go with the flow when their flight plans change, or do they collapse into crisis mode? How would they feel if their parents popped in for an unannounced visit or their project deadline got moved up by a week? 

Hint: This first date question also lets you know if that whole cake scenario may be a good idea down the road.

5. What’s on your Spotify Playlist?

We all know how powerful music can be. One simple note can lift our mood or take us back to a special moment in time. It can also have an impact on how you connect with someone. Believe it or not, sharing one’s taste in music can be quite personal. Scrolling through playlists is a dive into where you were in life when it was created. Whether it’s the all-90s alt-rock playlist you put together during your Scott Weiland obsession or the country jams you low-key love, music tells a story you can’t put into your own words. 

Asking this question on a first date also creates a great catalyst for stories you can tell. Like your first concert, the one band you’d miss the birth of your own child to see, or a song that always reminds you of your grandfather. Music can be a great equalizer and a fun way to get to know your date.

6. How would your best friend describe you? What about your boss?

On one hand, you get an idea of how their closest pal sees them, and if they even have a best bud (or maybe they consider their mom or dad their bestie, awww). This question can give insight into how they view and treat the people closest to them. On the other hand, you glean how they are on the clock when you ask about their boss. Are they motivated? Loyal? Underrated? Overworked? You get two distinct viewpoints into who they are, professionally and personally. Plus, who doesn’t like to humble brag a bit?

7. Where do you feel most out of place?

Instead of trying to figure out if they’re the life of a party or would rather listen to My Heart Will Go On on repeat than be the center of attention, this question dives into how they may respond in multiple scenarios, from giving a speech to scaling the side of a mountain. It’s a great way to share more personal fears, insecurities, and even goals. In an IG-perfect world, it may seem daunting to un-filter yourself emotionally around someone you just met, but being vulnerable gives you a better shot at building a solid connection. 

8. What’s your take on <insert hot-button issue>?

We know. Bringing up things like religion, politics, and other issues on first dates is more taboo than eating sushi with a fork, but that’s exactly why it’s on this list. At WhatsYourPrice we not only want to get you on great first dates sooner, but we also want you to find out if you may have a true connection. Why wait until the second, third, or fourth date to figure out you differ on an issue that could be a deal breaker? You may also find that you agree and spend hours sharing your solutions for saving the whales. 

9. What would your last meal be if you were on Death Row?

One swipe through any social media feed tells us how obsessed people are with their food. This question is a way to get people talking about something they love in a way that may seem irreverent (if not a little morbid), but can also be very telling. Admitting they’d want a giant ribeye and their mom’s famous mashed potatoes washed down with a nice bottle of Barolo can get you talking about great places to find a steak, other childhood memories, or even if they know whether orange really is the new black.

10. How do you feel about a second date?

At WhatsYourPrice we are all about empowering our members to go after what they want, minus the games. You shouldn’t have to wait three days after your first date to show your interest or to realize you’ve been ghosted. So go ahead and ask the question. You’ll either get to that amazing steak dinner faster or have the chance to connect with someone else.

The Final Answer

Now that you’re armed with 10 new ways to up your first-date game, login to WhatsYourPrice and connect with someone, ASAP! And if you’re still questioning whether you should take a chance on our revolutionary dating platform, the answer is YES. Sign up for WhatsYourPrice, today! Find more dating tips and tricks on the WhatsYourPrice Blog.