20 First-Date Questions That Are Way More Interesting Than “So…What Do You Do for Work?”
Few things are more nerve-racking than going on a first date. Not only do you have to figure out what to wear and where to go (after sussing out whether or not your date might be a total dud or creep, ofc), but you also have to figure out what TF to say. Honestly, knowing what to talk about on a first date might be the most intimidating part of the whole “finding a partner for life” thing.
That’s why if staring at each other over breadsticks to the sound of cricket chirps feels like a very real circle of hell for you, professional matchmaker and dating coach Thalia Ouimet says it’s a good idea to have some first date questions and conversation topics at the ready. “Having a few questions prepared for a first date will allow you to have a backup conversation in case you and your crush lose momentum,” she explains. “On a first date, your job is to have fun, see if there’s chemistry, and see if it’s a good fit for you.”
Beyond just random “getting to know you” questions, Ouimet suggests setting an intention going into the date to better demystify your suitor. Do you want to learn more about their work? Their hobbies? Their long-term goals? Since you’ve likely already chatted a little leading up to the date, knowing what else you’d like to figure out can help steer your conversations and questions. FWIW, a first date can be super telling, so don’t waste the opportunity by only making basic small talk. “I recommend having three to five questions ready so you can vet your crush and see if it’s a good match,” Ouimet says. “The biggest mistake people make on a first date is they don’t set an intention to gather information. Instead, they just go in trying to see if there’s chemistry.”
Now ideally, you don’t want to schedule a first date that’ll drag on forever. In fact, first dates should last under an hour and simply be a way to gauge whether or not there’s potential. That said, even if you’re just grabbing coffee, there’s a solid chance you’ll feel a little nervous going out with someone new for the first time, so don’t be too hard on yourself if the conversation lulls occasionally. It's normal! “Awkward silences with a complete stranger on a first date are inevitable,” Ouimet says. “However, if you’re a good conversationalist and you have a couple of questions ready, you’ll be able to better navigate the situation.”
If you’re still unsure about what to talk about on a first date, these 20 questions can help guide your convos and potentially uncover whether or not you’ve found your soul mate…or at least a solid candidate for a second date.
Basic Getting-To-Know-You Questions
Are there any hobbies or interests you’re just starting to explore and are excited about? Any you’ve done forever and still love?
What did you do this weekend?
Are you an introvert or an extrovert?
What’s your go-to karaoke song (and why)?
What’s one question you wish more people asked you? What’s one question you want to ask me, but are nervous about?
First date tip: You want to keep things super simple to start out, so don’t think you have to ask ultra-intense questions to make an impression. If you haven’t already covered the basics of where they grew up, if they have siblings, and what they do for work, this is your chance to do so. Beyond the standard Qs, Ouimet suggests hitting topics that interest you to see if you have similar hobbies and lifestyles. Even general questions about what they did over the weekend or what they like to do after work can reveal a lot about your compatibility.
Questions About Work
What made you decide to become a _______? How do you like it?
What’s your favorite part of the work day?
If you could do anything for work—and money wasn’t a concern—what would you do?
Do you think you want to stay at your current job/company long-term? Why or why not?
What’s your favorite way to spend a day off?
I know, I know—talking about work isn’t exactly The Most Fun Thing Ever. But! It’s a pretty big part of most folks’ lives. Deciphering whether or not your date is career-driven or places value elsewhere is pretty major. While you don’t want this to feel like an interview, a few light questions about work—such as why they do what they do, if they like their job, and how they spend their time off—can cue you into whether they’ll be climbing the corporate ladder or taking a more laid-back approach to work-life balance.
Questions About Childhood
What was your favorite holiday when you were a kid? Why?
Did you ever have a pet?
What was one of your best birthdays ever?
Did you have a childhood best friend growing up?
What was growing up like for you? (Did you move around a lot? Have an awkward middle school phase? Wear braces?)
Talking about your childhoods can be hit or miss, so you want to tread carefully and read the situation well. If your date is giving one-word answers or seems uncomfy, switch direction to something more neutral, like favorite foods or TV shows. If you’ve gotten the “do you have siblings/what do your parents do” questions out of the way, though, and it’s going well, diving into favorite holidays and special moments from childhood can show what sort of mems made an impression and how they might feel about family down the line.
Questions About Life Goals
Where do you see yourself in five years?
Do you like living here? Do you see yourself moving somewhere else in the future?
How often do you visit home? Do you feel like you should go more or less than you do?
Do you have any current goals or aspirations you’re working toward?
What makes you feel proud and/or fulfilled?
Again, you’re not hosting an interview here, so try to avoid making it seem like you’re running down their resume. Instead, ask some lower-stakes questions about goals, plans, and aspirations to a) see how motivated they are and b) get an idea if they’re trying to settle down or are still in their ~finding themselves~ era.
No matter what sort of topics you gravitate toward, Ouimet says it’s *super* important to steer clear of questions and convos surrounding exes. “A first date is not meant for you to talk about your past loves because there is no way to see if two people can form chemistry by discussing former relationships,” she explains. Don’t worry—you’ll have plenty of time to get into the nitty gritty exes convo if this interaction goes well. Lucky you! But for a first date, keep it light, casually inquisitive, and don’t make it obvious just how deeply you’ve stalked their socials.
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