First dates have a way of following the same script. Everyone shows up wanting the same thing: to figure out if this person is actually worth their time, but nobody wants to be the one who makes it feel like a job interview. So instead, people stick to the safe, standard first-date questions: their job, their last holiday, whether they prefer cats or dogs (a question that has never told anyone anything useful, ever). As long as the vibe is good and the conversation flows, everything is peachy.
And then three months later, you’re fully invested in someone, completely convinced that they’re your person, only to find out something so fundamental about them that breaks the whole thing apart. Not necessarily because of betrayal or because the feelings between you and the love of your life aren’t real, but because somewhere earlier, there was a conversation that could have changed the whole trajectory of the relationship, but no one thought to have it.
That’s the thing about the early stages of dating. The questions that actually matter rarely come up because they feel like too much, too soon. And fair enough, not everyone is built for directness. Some people will ask anything, straight up, without flinching, while others would genuinely rather chew glass than say something that might come across as too heavy.
So we put together a list of first date questions we think will save you a lot of time — almost as much time as Tova’s preference settings already saved you. And because we’re nothing if not thorough, we also took the liberty of adding softer alternatives for those who would rather not ask some of these directly.
1. What are you looking for right now?
This is the one question everyone knows they should ask, but almost nobody does. Instead, people spend weeks, sometimes months, in situationships, talking stages, and almost-relationships, carefully avoiding the one question that would tell them everything they need to know.
Contrary to popular opinion, asking this question this early isn’t desperate or intense; it’s simply a really efficient way to avoid getting your time wasted. It’s also the most important question on this list because the answer determines whether you’re going to spend the rest of the date asking the questions below, or just running out the clock until you can politely leave.
For those who’d love to ask this question, but are afraid of coming on too strong, try asking if they find dating fun or if it feels like more effort than it’s worth these days. It’s disarming enough that people actually answer honestly, and you can pick out the serial “daters” from the people looking for real connections.
2. Do you want kids?
With declining birth rates and the number of people actively choosing to remain child-free, making the linear “find a partner, get married, have kids” assumption might do you a lot more harm than good. Which is why this is a very important question because it’s one of those questions that, if left unasked, can do a lot of damage in the long run. At the same time, it’s a heavy enough question that leading with it on a first date might have your date mentally calculating how fast they can get to the exit, so we totally understand why a person might choose not to ask it outright, which is why we are sharing our little roundabout method.
First off, we advise that you weave it naturally into small talk and put that “cat or dog person” question to good use. Start there and then follow it up by asking whether they grew up with pets. And whatever their answer is, ask if they’d want their kids to grow up with pets. Most people will answer without realising what happened.
3. Where do you see yourself living long term?
Some might wonder why this made it to the list, and if you are, I’m genuinely happy for you because that means you haven’t had to delude yourself into thinking a long-distance relationship could work after waking up to the news that the person you’ve spent the last seven months falling in love with is moving from Austin, Texas to Alaska. So let’s keep it that way, shall we?
This question is an extremely important one when it comes to diaspora dating, because “home” is rarely a straightforward answer. Some people are here temporarily, some moved with no intention of going back, while for some, their current location is a stopover while they figure things out. All three of these are valid, but only one of them is compatible with your plans, so you should probably find out which it is before you start catching feelings.
For those who’d rather ease into it, put your small talk to good use. Ask questions like “If you could pick any city in the world to call home, which one would it be?” Let them dream a little. Then follow it with “more realistically, where do you see yourself putting down permanent roots?”
4. What role do your family and friends play in your life?
This question is less about how close they are to the people in their lives and more about how much those people influence the decisions they make. There is a meaningful difference between someone who values the counsel of the people they love and someone who cannot make a move without a group vote. While one suggests that a person is emotionally grounded, the other means you are signing up to date not just them but their mother, their three best friends, and whoever was able to get into their head first.
A good way to figure out where they fall is by asking something like “Are you someone who makes decisions pretty independently, or do you like to talk things through with the people close to you first?” It’s a simple and effective way to find out exactly how much outside noise you’re signing up for.
5. Relationship Patterns
This is a three-fold question, and the goal is to determine whether your soon-to-be beau is cut out for a serious relationship. The best way to do this is by figuring out what their track record looks like. i.e., have they ever been in a serious relationship, how long did it last, and how did their previous relationships end.
These three questions are best asked in sequence because each one builds on the last, and together, they tell you more about a person than almost anything else on this list. These questions give you insight into their ability to show up for someone long-term, how long they are capable of sustaining something real, and, perhaps most importantly, how much self-awareness they have about the role they played and how it resulted in the end of their previous relationships.
That answer to the last question is worth paying close attention to because someone who can reflect honestly on why a relationship ended without rewriting history or casting themselves as the victim in every story is a person who knows how to hold themself accountable.
To get your answers without making it feel like a sit-down interview, start with a simple “have you ever been in a serious relationship?”, let them talk, then follow up with “what’s the longest one you’ve been in?” By the time you get to the “why did it end?” question, the conversation has already done enough of the work that it feels like genuine curiosity — which it is.
6. Are you friends with your exes?
There isn’t a universally acceptable answer to this question. It all depends on what you’re comfortable with. Some people maintain cordial relationships/genuine friendships with exes, and there is nothing necessarily alarming about that. What you need to know is the reason that relationship still exists, whether decent boundaries are in place, and whether anyone is quietly holding out hope for a reunion.
To start things off, you can simply ask what their perspective on being friends with exes is. And then follow up by asking if they are friends with any of their exes.
7. What does your ideal relationship look like?
This question surfaces a lot at once — expectations, gender roles, how they think about partnership, whether they believe in 50/50 or have a more traditional idea of how things should be divided. People will tell you exactly who they are when you ask them to describe what they want, because a person’s wants in a relationship is almost always a reflection of how they see themselves in one.
Asking questions like “What’s something you feel really strongly about when it comes to how a relationship should work?” is a great start to understanding what a relationship with a person is going to look like.
8. Is faith something that plays a big role in your life?
This is an important question to ask because assuming you already know the answer based off a person’s perceived background is never a good idea.
In some cases, it isn’t particularly alien to find out that faith is less of an active personal choice and more of something that was culturally inherited, and this affects the way/the extent to which a person’s faith is expressed, practiced, or how much of it informs the decisions they make. This means the question that should be asked isn’t merely what religion they identify with but how that belief shapes them.
There isn’t really a roundabout way to ask this. It needs to come up directly. The easiest way to get there is by sharing where you stand first, and giving the other room to express themself. That way, you take the pressure off and it flows like a conversation rather than an interrogation.
First dates are a lot of things — nerve-wracking, exciting, and occasionally, a great story you’ll be telling for years. But more than anything, they are an opportunity to find out whether the person sitting across from you is worth pouring more of your time into.
So ask the questions. All of them, if you can. And if you can’t bring yourself to ask them directly, you now have the softer routes in. Either way, your future self will thank you.
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