Hey Kate, what’s the biggest mistake men make on dates with women?
Not asking anywhere near enough questions. Or, in many cases, not asking any questions at all.
Really? That’s the biggest mistake they could make? Worse than showing up without showering/brushing one’s teeth, yelling at a restaurant employee, or sexually coercing one’s date?
While these kinds of behaviors are obviously not ideal if you’re trying to impress someone (to say the least), they’re so egregious that it’s hard to think of them as “mistakes” so much as “behaviors you should’ve known would turn someone off, and it’s kind of weird if you didn’t know that.” If you struggle with any of the above behaviors, your issues are probably above my pay grade, although I wish you the best of luck addressing them ASAP.
Not asking questions on a date is often an actual mistake, though – in that a lot of people who do it seem to be unaware that they’re doing it, or unaware that it’s deeply rude and off-putting. This post is mostly for people like that. Hi; welcome!
Are you sure this is such a rampant problem? Surely some men ask questions on dates?!
Yes, obviously some men ask questions on dates. There are over 4 billion men on this planet; it would be pretty wild if they were all socially out-of-touch in this particular way.
However, it’s enough of a phenomenon that countless trend pieces have been written about it; here are some articles from MEL Magazine, Marie Claire, Bustle, and the Sydney Morning Herald on this issue. Anecdotally, my friend Girl on the Net has written many blog posts about abysmal dates with men who ask no questions – and it’s an issue I’ve observed myself on many dates with men.
But I’m a man and I do ask questions on dates!
Great! Keep it up. Hopefully one day a majority of men will do the same. (Perhaps you can help by sending this post to all your bros.)
This problem isn’t limited to men! Some people of other genders do it too!
Sure, that’s definitely true! However, there are specific sociocultural factors that lead men to do this far more often.
Studies overwhelmingly show that men talk more than women in mixed-gender conversations, and don’t listen as well when others talk. Some researchers in this field have attributed this to differences in rhetorical strategy: “men learn that it is important for them to assert status and to appear a leader,” while women communicate “to establish and maintain harmonious relationships with others.” (Some sociolinguists, like the late Princeton professor Deborah Tannen, think these imbalances have more to do with societal power structures than with anything inborn/biological.)
Okay, fine, let’s get into it. Why is it important to ask questions on dates?
I’m so glad you asked! There are a few key reasons to ask questions on dates…
- To communicate interest. Presumably, if you’re on a date with someone, it’s because you’re interested in them – but if you ask them zero questions, you’re going to seem entirely disinterested. Is that how you want to come across? If so, why are you on the date in the first place?
- To be more likeable & attractive. Studies show that “people who ask more questions, particularly follow-up questions, are better liked by their conversation partners.” And you want your date to like you, right?! People who ask questions are also “perceived as higher in responsiveness, an interpersonal construct that captures listening, understanding, validation, and care.” These are all great qualities that many people look for in potential partners.
- To demonstrate social sense & conversational skill. It’s just good manners to keep a conversation well-balanced, rather than expecting the other person to single-handedly carry the entire interaction. Not to mention, I’d never even consider continuing to date someone who hadn’t yet mastered the basics of conversation, as it’s an absolutely core skill in any relationship I’d want to be a part of, and I think many people feel the same.
- To assess compatibility, which is arguably the main point of going on a first or second date. As Girl on the Net points out in this fantastic blog post, asking questions on dates is a way of screening for things that matter to you in a relationship, so the two of you can decide if you’re a good fit and want to continue seeing each other. You can’t assess that without asking at least some questions.
- To establish intimacy & attraction. For many people, sexual attraction sparks at least partially from a sense of emotional intimacy – and it’s difficult to feel intimately connected with someone who knows nothing about you because they’ve asked you zero questions. It’s genuinely sexy to be asked interesting, astute questions about oneself, not only because it demonstrates social skill but also because intimacy is based on the mutual desire to know/understand each other more deeply.
What if I can’t think of anything to ask?
Well, first of all: Do you actually like the person you’re on a date with? Are you actually interested in them, curious about them, eager to get to know them better? If so, I’m sure there are some things you can think to ask them. What do you wonder about? Ask about that.
If you genuinely can’t think of anything that you want to ask the person sitting across from you on a date, either you’re just not that into them (which is fine, but you shouldn’t go on more dates with them if that’s the case!), or you need to develop your curiosity like a muscle. Practice this skill in all your connections, not just romantic or sexual ones. Ask people how their day went, what they’ve been up to lately, what’s on their mind, what they think of the latest kerfuffle in the news, or any other (appropriate) question that pops into your head. Open-ended questions are usually best, as opposed to “yes or no” or “do you prefer X or Y?”-type questions, although those are fine too. The more you practice, the easier it’ll get, until it starts to come more naturally.
One wildly easy way to ask someone a question on a date, though, is just to flip their own question around on them. For instance, if they ask “How was your day?” you can give your answer and then say, “How about you?” This sounds screamingly obvious, I know, but you would be amazed how many men don’t even do this. It’s extremely, extremely easy. There’s no excuse not to do it. As Girl on the Net wrote in a comment once: “Literally a man could write ‘how about you?’ on his palm in biro before a date as a reminder to throw it into the conversation once or twice, and he would be doing better than 80% of the men I have been on dates with throughout my life.”
Oh yeah, and here’s 50 questions you can ask people on dating apps and 30 questions you can ask on dates. There, now you really have no excuse!
What if I hate small talk, though?
Who said anything about small talk?! Certainly you can ask small-talk-y questions on a date, and usually it shows good social sense to at least start in shallow waters conversationally – but you can ask bigger, deeper questions, too! Some examples: “What are you passionate about?” “What’s your favorite memory in [this neighborhood/this city]?” “What’s the last thing that made you laugh really hard?” “What are you looking for in a relationship?” “Do you think we’re alone in the universe?”
When I ask questions, do I have to actually listen to the answers?
Yes!!! or else why bother asking them? Seriously, if you’re that disinterested in your date, you should stay home. I’m not even trying to be shady here; you would probably have a better time playing a dating sim than going on a date with an actual person. Dating people requires being interested in people. If you’re not interested in people, ask yourself why you want to date.
Listening to – and acknowledging – someone’s answers to your questions is a vital part of how conversations build intimacy. If I tell you a story and you don’t react to it, I might as well have told it to a brick wall. Listen to what your date says, utilize active listening techniques, and acknowledge what they said (e.g. “Wow, that sounds like it was really stressful!” or “Damn, that’s amazing!” etc.) before you consider jumping in with your own story in response. Remember, the objective is to build connection and rapport, not to outdo each other conversationally.
This is too hard and makes me want to give up on dating!
If the “human connection” part of human connection feels too hard for you right now, that’s okay. I get it. I have days like that too.
But the fact is, if you want to connect with human beings, you have to have at least a few skills in your back pocket that enable you to do that. And asking questions is one of the most basic building blocks of conversation, so it’s a skill you should develop, even if you’ve struggled with it until now. Trust me, there are few skills more worth learning than this one, at least if you value connection and intimacy of any kind. There are plenty of resources out there that can help you get better at conversational skills, like Dr. Nerdlove’s blog posts and Camille Virginia’s book The Offline Dating Method – and simply practicing will help a lot.
When you find yourself wanting to “give up,” perhaps put yourself in the shoes of women who’ve gone on countless dates with men who haven’t asked us anything. It’s not just boring and exhausting (although it absolutely is those things) – it’s also deeply disheartening and depressing to go home at the end of a date, having been asked nothing at all. I have spent so many nights crying after this kind of date. It always makes me feel like worthless garbage that even someone who claimed to be interested in me couldn’t muster enough actual interest to ask a question. It’s soul-destroying, and makes me want to give up on dating sometimes. So I understand that nihilistic impulse, but please ask yourself: Is it really that hard to think of things to ask the person you’re ostensibly interested in? And if so, why is that?
What should I do if I am [neurodivergent/socially anxious/etc.] and therefore can’t ask questions on dates?
I mean, if you literally can’t, then you can’t. You know your limitations best.
That being said, as I’ve already emphasized, asking questions is a very basic aspect of conversation, which is a very basic aspect of human relationships. So if you intend to have human relationships in your life (whether romantic, sexual, platonic, or any combination thereof), this is a skill worth developing, even if it’s difficult for you. Most skills worth learning are initially difficult to pick up. That’s part of what makes it so rewarding to learn those skills. As Alexandra Franzen says, “Are you willing to feel temporarily uncomfortable so that you can accomplish something that is permanently amazing?”
That being said, if you really, truly feel like you can’t have give-and-take conversations of this type and will never be able to, then it’s possible you’d be better off dating folks whose style of connection is similar to your own – in which case you might prefer to date within neurodivergent/socially anxious/etc. communities rather than seeking out dates on mainstream dating apps etc., where most people will be expecting a more conventional conversational style.
Some people just don’t ask questions. Don’t you think it’s unreasonable for you to expect your dates to ask you questions?
No, it’s not unreasonable for me to expect that anyone who wants to date me should be interested in me, and should be able to express that interest. Asking questions is the most basic way of expressing interest. If someone can’t (or won’t) do that, I won’t even be able to develop an attraction for them, let alone do all the other things I like doing with people I’m dating, so there’s no point in continuing to see them.
It’s certainly true that some people have a less question-based conversational style than others. I still think those people have a lot to gain from learning how to ask questions, just as us question-askers can sometimes get better at simply interjecting our own stories/thoughts when we’re talking to someone who never asks us anything. But it can be frustrating to try to bridge these gaps, so oftentimes it’s a lot easier to date someone whose conversational style already matches yours.
I think I fucked up, and didn’t ask enough questions on my most recent date. Is this salvageable?
Possibly! When I’ve arrived home from a first date feeling miserable and alone because the other person didn’t ask me anything, usually I’d already made the decision to stop seeing them – but I think it would’ve helped a lot if they’d sent me a message within the next couple days, saying something like:
Hey, that was so much fun! Realized I might’ve talked your ear off cuz I was kinda nervous – but I want to get to know you better! Can I take you out again and ask you more questions this time? Also, how’s your day going?
Notice that there’s an actual conversational question at the end of the message, to prove that you are already following through on your intention to ask more stuff. It’s such a bummer when someone promises they’ll change their ways and then just… doesn’t.
What should I do if I’m on a date with someone who isn’t asking me any questions?
Such a tricky and annoying situation to find yourself in!! Broadly speaking, I think you have 5 main options here…
- End the date. Honestly, I wish I’d done this more often. You don’t have to do it rudely if that feels too difficult; you can just be like, “I’m not feeling the chemistry I’m looking for, so I’m gonna head out,” and then pay your half of the check (if applicable) and hit the road. Sure, they might ask you annoying follow-up questions (“Seriously? But why?!”), although they also might not, considering that asking zero questions is their whole problem in the first place…
- Leave more silences. Sometimes I ask people so many questions so eagerly that they don’t have enough time/space to think of questions for me and actually ask them. I am a journalist and have been trained to fill all the “dead air,” after all! So I’ve had to learn that sometimes, when someone finishes answering one of my questions, I can just nod wisely and wait to see if they ask me something back. For some people, an awkward silence can be a reminder: “Oh yeah, I’m supposed to ask stuff, too!”
- Ask them, “Is there anything you want to ask me?” This is more direct and therefore more scary, but entirely valid. It’s possible they’ve forgotten to ask you stuff because they’re nervous or enthralled by your conversational skill (you charmer, you!), so they might appreciate the reminder to hold up their end of the convo. Some situations may warrant a slightly more confrontational “I’m noticing that you’re not asking me about myself – any particular reason for that?”
- Just jump in with your own stories/responses. For instance, maybe you ask your date about their favorite movie, listen to their answer, respond/react to their answer, and then say, “My favorite movie is…” Personally this isn’t my preferred option because a) it annoys me to do that extra labor when I shouldn’t have to and b) I am never convinced someone actually cares to hear my answers if they haven’t asked me a single question… but it’s still good to have this strategy as an option if you need it, because lord is it ever exhausting and irritating to just listen to someone monologue for an hour+!
- Suffer through it. This is usually what I do, and I’m not proud of it – but there are times when it just doesn’t seem worthwhile to try to teach someone how to have a conversation, especially if I’m not even that into them. Sometimes I’m just like, “Well, I’m already on this date. Might as well enjoy my cocktail, pretend I’m a world-famous interviewer who’s here to make an ordinary person feel fascinating, and leave as soon as we’ve paid the check.” 🤷🏻♀️
Can I reject someone/decline to go out with someone again because they didn’t ask me enough questions? How do I tell them that?
You are allowed to decline to go out with someone for any reason you want, and I would say that “shows no interest in you” is a damn good reason.
When offering a reason, I have tended to say that we don’t have the conversational chemistry I’m looking for. I want them to know that the issue was conversational, so that they can hopefully fix it for future dates’ sake – but I don’t always have the spoons to get more specific, and that’s fine. A friend of mine will straight-up say “You are not interested in me” when asked about this, which is often met with protestations (“Of course I’m interested in you!!”) – but as I mentioned above, when you reject someone for being incurious, sometimes they are just as incurious about the reason for the rejection (possibly because they indeed are not very interested in you!), so you may not even need to explain yourself.
Do you have any theories on why men generally ask so few questions on dates?
I do! (Please forgive me for the very hetero and generalized answer to follow; I’m speaking very broadly about wide-ranging social trends, which, by its nature, leads to analysis that is neither universalizeable nor precise.)
I think heterosexual culture, as a whole, tends to position women as the gatekeepers of sex and men as the pursuers of sex. This can result in a dynamic where early dates feel like a job interview for the position of boyfriend (or husband, or fuckbuddy, or whatever the case may be) – the man feels, on some level, that he needs to seem impressive and authoritative, standing up to the woman’s scrutiny as she assesses him through questions. However, while men are trying to be a “winner” and come out victorious over their imagined competitors, women are often looking for a lover, a partner, not a winner (to borrow language from Emily Nagoski’s Come Together). You can’t really develop a mutual, equitable connection from a place of competitiveness and trying to prove yourself.
I think some men feel such a sense of scarcity in their dating lives that they’re happy just to be on a date with a woman at all, and don’t want to risk rocking the boat by asking anything that might reveal an incompatibility, even though that filtering process is largely the point of going on dates. There are also men who see it as somehow unmasculine to take a heartfelt, proactive interest in women’s thoughts and feelings. And there are men who harbor such skewed views about women that they can’t conceptualize us as anything more than a pretty face and a pleasant presence – in which case, why bother inquiring about our inner lives? Those men barely think we have inner lives!
But of the men who ask zero-to-very-few questions on dates, I think the majority are probably decent dudes who want to connect with women… and it is for them that I have written this giant-ass blog post, in the hopes that they will take away this one all-important lesson from it: Ask your dates questions about themselves. Show an interest in the people you claim to be interested in. All your relationships will be better for it.
