If you think about the last first date that we went on, you probably agree that you didn’t have the best, most fascinating conversation ever. First date chatter is often very superficial and when there are awkward silences, sometimes people can end up talking about something as dull as the weather. We often joke that a first date can seem like an interview, and yet asking questions is a regular part of dating. It’s the way to get to know someone. Here are 10 questions that you should always ask on a first date because they’ll help you really get to know someone’s personality.  

10. What Was The Worst Job You Ever Had?

We know that you’re going to ask someone what they do. It’s a pretty normal first date question. But that doesn’t really help you get to know their personality… and if they simply respond, “I’m a lawyer” or “I work at a pub”they might not say anything else, and the conversation could grow silent once again. Instead, try asking, “What was the worst job that you ever had?” This will allow your date to open up and share a (hopefully) hilarious bad job story. You’ll definitely find something out about them (even if it’s just that you don’t share the same sense of humor… but, hey, you have to find that out at some point).  

9. Is Your Current Job Your Favorite Yet?

You want to know our date’s job, but you also want to know if they absolutely love what they do. This is particularly important if you love your job, and if a great work ethic is a quality that you find to be totally attractive. If you ask someone if their current job is the best one that they’ve had and their favorite job yet, you’ll learn a lot about them. You’ll find out about some of their work history, along with what gets them excited to wake up in the morning and head to the office. And that’ll be a fun conversation to have.  

8. What’s Your Favorite Thing To Do On The Weekend?

How does your date spend their weekends? It’s good for you to find out because if you get along and start dating each other, you’re going to be spending precious Saturday and Sundays as a couple. And if they love hiking and you’re more interested in curling up on the couch with some coffee, then that might not be the best match. You should ask, “What’s your favorite thing to do on the weekends?” so you can learn about our date’s personality. Are they bookworms who want to go for brunch and then stay in all day to read? Do they like to go out with friends? Host parties? You have to know.  

7. Do You Like To Cook?

Everyone approaches feeding themselves differently. Some of us cook every night and meal prep on weekends. Nothing thrills us more than a pot of pasta sauce on the stove that we know will feed us for days or finding a new recipe that promises that dinner will be on the table in fifteen minutes. Asking our date if they like to cook is a great idea since you’ll know if they’re a take-out pro or if they really do love getting into the kitchen. It’ll also set up your expectations for future dates. If they always want to go out, then you’ll know why, but maybe they love to cook and will make you dinner (how romantic).  

6. What Food Do You Wish You Could Eat Every Day?

Sure, your date might not be a foodie who thinks that the kitchen is their domain, but they definitely love food (or at least they eat it… hopefully they love it, though, since food is the best). Everyone has a favorite food that they wish they could eat all the time, whether it’s cheeseburgers or fries or potato chips, or something more meal-like such as chili or curry. You can ask your date, “What food do you wish you could eat every day?” and you’ll learn yet another thing about them. If the first date goes well, you can even take this information and cook for them… or go to a restaurant that serves that kind of food. That works, too.  

5. What’s One Place You Would Live If You Could?

Sure, learning if someone is into travel is definitely a good idea, and it’s one of the most classic first date questions. But asking someone where they would live if they could is an even better question since it goes one step further. Thinking about where you would consider moving is like a window into your soul. Are you a beach bum who dreams of waking up to sunny skies and blue water every day? Do you want to live in a thrilling city like New York or London? Or do you wish that you lived in the country? If you ask your date where they would live if he could, you’ll find out what kind of person they are.  

4. Are You Into Podcasts?

It seems like everyone is super obsessed with podcasts these days. From health to fitness to mindest, from TV to movies to news and interviews with famous and/or interesting people, there are so many to choose from, Asking your date if they like listening to podcasts will not only tell you if you have this fun thing in common, it’ll also show you more about who they are. If they’re into living a healthy lifestyle, for example, then maybe those are the kinds of podcasts that they subscribe to. At the very least, this part of the date should make for pretty good conversation.  

3. What Was The Last Movie You Saw?

Whether someone is a pop culture addict and sees all the movies that come out in a month or just goes occasionally, chances are, your date has seen a movie pretty recently. Even if they just watched something at home, that totally counts, so it’s a good idea to ask them about the last movie that they watched. This will give you some intel in terms of what kinds of films they enjoy. Are they a horror buff? Into thrillers? Actually into romantic dramas… or do they only stick to comedy? It’s good for you to know for sure, and we can tell them what we like to watch as well.  

2. Do You Enjoy Going For Walks?

Sure, we’ve all heard the cliche “I like long walks on the beach” dating line but many of us love going for walks around our neighborhood and our city or town. It’s a great way to forget about whatever’s going on in our lives and get some nice fresh air. If you ask your date, “Do you enjoy going for walks?” you’ll learn about their personality and find out if they’re a quiet, contemplative kind of person who loves to walk, or if they don’t ever really slow down and have a different kind of personality. If you both love going on walks, then you’ve found another thing that we have in common, and it can be a future date activity.  

1. Are You A Hopeless Romantic?

Yup, we’re going there: the final question that you can ask your date is if they’re a hopeless romantic. Sure, this might seem bold (and, okay, it is) but that’s exactly why it’s a good idea. This really gets to the heart of the matter and will allow you to see if this is the right person for you. If you’re super big on romance, then you want a partner who is, too, and it’s nice to hear that they’re on the same page. And if you’re not, then you want someone who doesn’t go for all that cheesy stuff. It might be tough to ask this, but what do you have to lose?


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