Estimated reading time: 20 minutes
Hello Doc,
My current letter is inspired by a letter you answered recently, the subject of it, Jerry, and lead to my needing to ask about asking people out and taking things slow.
One sentiment/advice I’ve seen a lot online, and especially here, is about being direct when asking someone out. For me, this usually translates to using words such as “date” in a sentence like, “I would like to get to know you better. Do you want to go on a date with me?” And this is after getting to know a person through multiple interactions and trying to flirt with them. But I always get rejected. My friends, both men and women, and my therapists told me this makes me come across as unnatural and robotic, like a Dalek from Doctor Who. The advice I got is to be covert about it, not use the word “date,” and, if asked what my intentions are, to be coy about it. But first, I feel that this approach goes against who I am as a person, second, if that person was interested, then the way I ask them out should not be an issue, barring being an asshole about it, and third, I feel that I need explicit approval to be more intimate.
I once “got together” a couple of times with a woman I met at a hobby class. We did activities and got lunch, but the moment I used the word “date” to describe what we were doing, she changed her tone, told me that she did not think these were dates, and that was it. The only time I was successful, I invited someone to do an activity we were both interested in, and at the end I asked her if she thought that was a date, and the answer was positive. But during that time, I did not try to explicitly flirt through touching or sexual innuendos, I was just being myself and was genuinely interested in getting to know more about her. From our second date onward, I was more intimate.
I know that everyone is different and, to an extent, my question can be viewed as asking for a formula. But I am genuinely baffled by it. Is being direct actually not about using words, but about testing the waters before asking someone out? How? Is my wanting an explicit OK a way of trying to protect myself against rejection? What trips me up is that eventually someone needs to ask the other person out, and in our society, it is usually the guy. I feel this pressure to lead, and if I just wait around, nothing happens. So how do you take things slow, be less robotic, but still progress toward something?
Mr Robot
The disconnect you’re running into here isn’t the word “date”, it’s about dates. The concept, not the word describing it. Focusing on the word is missing the forest for the trees; there’s a lot of context and application issues that’re in play.
The experience that Not Always Right had with Jerry is one that many, many women have experienced, in one form or another: guys who have hidden their interest in plausibly deniable ways, only to spring it onto their companion without warning or invitation. It feels like a betrayal, something that not only changes the context of whatever outing they were on but also the nature of the relationship they thought they had with this person. More often than not, they thought they were having some sort of platonic social event with a person they know. They thought that whatever they had agreed to was something specific – it may have been work-related, it may have been friendship, it may have been connected to school, networking, or any number of other possibilities that did not include any sort of romantic or sexual engagement. Finding out, either in the middle or at the end, that the other person saw this as a date comes as a shock.
This, understandably, leads to a whole lot of second-guessing and recontextualizing every interaction they’ve had. Some find themselves wondering if maybe this was somehow their fault for not noticing the signs. They may wonder if they were leading the other person on by accident or encouraging them in some way they weren’t aware of. Others find themselves having to question whether their entire relationship with this person was not what they thought; they thought they were friends, peers, co-workers or potential business partners and resources. Now they have to ask whether this person was always deceiving them or not, and whether they can even trust that this person is honest with them about other things. After all, if they’ve been dishonest (and please note that I say dishonest, not “lying”; there’s a difference) about this, what else have they been dishonest about?
Many folks experience both of these and more. In fact, lots of folks feel not just betrayed and lied to, but also find that they have a hard time trusting other people in their lives who might have likewise been hiding some agenda from them. That’s a very painful and lonely feeling to have and one that makes it a lot harder to take people who are acting sincerely and in good faith at their word.
Now part of the problem is that in a lot of modern cultures, there’s a real aversion to being straightforward about what your interests and intentions are. A lot of it comes from the way social mores have changed; while formal courtship practices may have fallen by the wayside, other taboos like open discussions about sex or romantic interest persist, especially for women. The various written and unwritten rules – including a literal book called “The Rules” – about social signals and what seemingly anodyne interactions “mean” and why it’s “bad” to be up front create an atmosphere of uncertainty and discomfort for everyone. The whole “wait, is this a date??” moment, followed by a run-down of what made something a date or not a date, is a trope that still persists in pop culture and media.
On top of that, there were also a number of social landmines that came into play because of all that vagueness and everything that kept going unsaid. There used to be frequent joking-but-not-really “jokes” about things like “women should never order the lobster when out to dinner with a man,” in part because the implication was that the woman who did so was either signaling an interest in sleeping with the man, or else creating an obligation to put out in some way, because of the cost of the entrée. It seems absurd… right up until you see guys complaining about how their date ordered such-and-such or their dinner date cost this-and-that and then their date bounced, ghosted or otherwise turned them down… the implication being that she broke the contract that supposedly existed between them.
(There’s also a lot to be said about the sheer what-is-going-on attempts to sort friendship from romance between women who love women, but that’s for someone who is not me to get into.)
This is why being coy about your intentions tends to get a lot of side-eye under the best of circumstances; it perpetuates a system that ultimately frustrates everyone involved. Under the worst of circumstances… well, see above.
All of that is why I’m an advocate of being up front that you’re asking someone on a date, and to make sure that it’s clear that this is a date. Using the word is the easiest way to ensure that everyone is on the same page.
This is why, in the examples you bring up, the problem isn’t the word. The woman you mention whose mood changed when you asked if this was a date didn’t have that reaction because you used the D-word. What she was doing was making it clear that a) this was not a date and b) if she had thought that this is what you intended, she would’ve turned it down. She was happy to go out with you as a friend or to discuss your mutual interests in the hobby group, but she wasn’t interested in going on a date with you. Being emphatic like that was to drive her point home in no uncertain fashion.
The same goes with the women you’ve asked out who’ve turned you down. The problem wasn’t that you used the “d-word”, it was that they weren’t interested in you romantically and were turning down the date. The fact that this was happening after multiple interactions and flirting attempts doesn’t really change the math; it all boiled down to the fact that there wasn’t any interest. That’s why how you worded the ask isn’t the issue. There wasn’t some formulation or specific way of asking that would change their mind; they just weren’t interested.
On the other hand, the “successful” example you mention was one where the person was interested and was under the assumption that this was a date all along, even if you were behaving in a relatively chaste manner at the time. The difference here wasn’t that you didn’t use the word, it was that she liked you and wanted to be on a date with you.
I understand the worry about the whole “come off like a robot” issue, but frankly, I think that fear’s overblown. While I understand the worry, especially if you’re varying flavors of neurodivergent, the truth is that this has more to do with people’s discomfort with openness and honesty about their interest or intent. As a general rule, if someone likes you and would like to go on a date with you, being a little stiff in how you ask them out isn’t going to be what changes their mind. If anything, they may think it’s charming. People understand nervousness, they understand being a little awkward in phrasing and everyone’s had experiences where they’ve tried to say something and had it come out weird or stilted or in some way that was less than suave. Someone with even an ounce of empathy is going to understand, because they’ve done it themselves.
Now with that in mind, the example you gave of how you ask someone out could use a bit of tweaking. I realize that you’re giving a generic example, but I find that asking someone on a date goes more smoothly when you’re asking them to do a specific thing at a specific place and on a particular day and time. This means that they’re being asked to say yes or no to something concrete – getting drinks at this new cocktail bar next Saturday or going to shoot pool after work on Thursday – rather than some vague and nebulous outing. This way, not only does it let them decide if that’s something they want to do with you (and hopefully be excited to do so), but they can turn down the specific offer without turning down the person. If they have some objection or prior obligation – they don’t drink alcohol, the pool hall is too smokey, they’re busy on that Saturday – they’re able to say “I’d love to but $REASON; how about $ALTERNITIVE_IDEA/$DIFFERENT_DAY_AND_TIME?”. It also means that you’re taking charge and showing initiative instead of opening negotiations or asking them to do the planning.
So, the way I would suggest you frame it would be “Hey, I’m really enjoying talking to you, and if you’re interested, I’d love to take you on a proper date. How do you feel about pinball and craft cocktails at Highland on Saturday?” It’s a specific offer with clear intent, and they can say “yes”, “no” or “yes, but…” with the full understanding of what’s being asked of them and what to expect. If you don’t say the word “date” in the ask, you can also say something along the lines of: “just so we’re all clear… you know I’m asking you on a date, right?”
If you find yourself out with someone where you’re not sure about what this is, but you feel like you’re catching a vibe… just ask. Asking for clarity is always better than guessing and getting it wrong, even if you’re not smoother than a 90s R&B solo. And again, the ask doesn’t need to be particularly complicated or involved. All that really needs to be said is “hey, I just wanna be sure we’re on the same page and it’s totally cool if the answer is no but… is this a date?” If she says no, then you can say “Ok, cool, thank you, I just wanted to make sure.” If she says “yes” – and you want to be on a date with her – then congratulations, things worked out better than you expected.
And to preclude the worry I know you may have: if she asks (she probably won’t, but if she does) why you thought that this was a date? All you have to say is “I wasn’t sure and I didn’t want to presume.” That’s it.
The last thing I would say is that just because someone says no to a date doesn’t mean that you have to stop talking to them or give up all interest. All it means is that they’re not interested in a date with you, not that you’re dead to them forever more. You can still hang out, you can still be friends, you can even flirt a little if they’re receptive to it. Just don’t hit them up for another date unless you’re getting stronger (and preferably clearer) signals of interest than you had been previously.
Good luck.
Hi DNL,
I’m in a similar position to many of the people who’ve written in recently. I’m a single man in my early 30s, doing fairly well in life overall, but my social life has always been inconsistent and my romantic life virtually nonexistent.
To be honest, it’s always been this way. I’m 32 now, and I still don’t really understand why. Socially, I can hold conversations easily and generally get along well with people, but I’ve never managed to form the kind of close connections where people regularly meet up, message often, or naturally become part of each other’s lives. Meanwhile, I’ve watched others move through relationships, dating, marriages, and everything in between with what seems like very little effort. For some people, it feels as simple as showing up to a party or hobby group and effortlessly meeting someone new.
I’ve always felt like I’m fundamentally the same as everyone else, except none of that ever seems to happen for me. Over time, the loneliness has turned into a mix of resentment and bitterness. I feel like I missed out on “young love,” and I’ve become increasingly cynical about the idea of eventually finding someone, worrying that I’ll only ever be someone’s safe option rather than someone they genuinely wanted. I’ve given up at this point, honestly.
That said, something strange has happened recently. For the first time in my life, I’ve actually had women show romantic interest in me. More specifically, two different women asked me out for drinks this month, both completely unexpectedly and, ironically, I turned both of them down because I wasn’t interested.
The first woman is someone from a hobby group I attend. I wouldn’t call myself especially popular there, but I chat with a decent number of people at events, and she was simply one of many acquaintances. We barely spoke beyond occasional exchanges, and she rarely even attends the events herself. She’s perfectly nice, but we have some obvious incompatibilities and she just isn’t my type. I was genuinely caught off guard when, after months of barely speaking, she suddenly messaged asking if I wanted to grab a drink. I agreed, while making it clear I meant it platonically, and although we’ve spoken a bit more since, nothing has really come of it.
Then, about a week later, something similar happened again, this time with a colleague. We’d barely interacted before, yet there she was asking if I wanted to get a drink after work. Again, I politely declined because I simply wasn’t interested in her that way.
If anything, I feel more hurt and confused now than I did before. I already believed I wasn’t the kind of man women could genuinely be interested in, and part of me still believes that because I keep dismissing these two experiences based on who they were. I also keep asking myself why. Why did they ask me out? I didn’t have much of a rapport with them. I haven’t changed as a person. I’m still the same guy who spent years being told he was a catch while constantly seeing evidence that suggested otherwise. So why does it suddenly feel like the evidence is changing? Why was I completely ignored before? What do I even do at this point?
Why Me Why Now?
This is going to be an odd comparison, WMWN, but I think it’ll be apt – there’s a moment in Peter S. Beagle’s The Last Unicorn, where the titular unicorn meets Molly Grue – an older, plain-faced woman who, up until that moment, has been playing the “Maid Marian” role among a troupe of men who might charitably be called Robin Hood LARPers. In a moment where Molly has been confronted with magic, true magic that she always thought wasn’t real, she has an unexpected reaction: she turns to the unicorn and yells “HOW DARE YOU? How dare you come to me now, when I am this?” She’s upset that this mythical creature who is associated with youth, virginity and beauty has shown up when she is at the stage that women are considered to be “washed up” and are just background characters in the lives of others; where was the unicorn, as Molly puts it, when she was new? When Molly was one of those unspoiled maidens they supposedly come to? Why is this being offered to her at a period when she’s no someone who fits the role of someone who a unicorn would come to?
And the unicorn replies “I’m here now.”
I bring that up because there’s a similar dynamic here: you’re experiencing something that you believe was intended for people who are younger, something that’s supposed to align with a narrative in your head, and it didn’t. But it’s here now. Being upset that it’s happening later than you expected risks blinding yourself to the fact that it’s happening now, and perhaps the important part is appreciating that instead of being angry at what you missed. You can look back and be upset, or you can look forward and enjoy what you have now… but you can’t do both. So you have to decide whether holding onto that past pain is more important than embracing your life now.
The fact that you didn’t have a particular experience at a particular age doesn’t mean anything other than you didn’t have that particular experience.
It doesn’t mean that you screwed up or failed at something, it just means that this is your life and your experiences, not anyone else’s. It’s honestly not that different than not being the star quarterback in high-school or prom king or any other overly romanticized event. It’s just life, and it’s the belief that you messed up because you missed out that causes you more pain than anything you actually missed.
Love isn’t more special or significant when you’re young; it’s confusing, it’s scary, it’s chaotic and it tends to be like a shooting star: brilliant and gone in a flash. Most of the time it’s not even love, it’s infatuation paired with the surge of endorphins that come from having a new partner, and people mistake it for love… and then become confused and hurt when it goes away or falls apart on them. We romanticize it, we dramatize it and we overstate its importance because it’s drama made manifest, and drama makes for great entertainment. But there is always the problem of mistaking the drama for reality and assuming that this is how it’s “supposed” to be, instead of a fiction based on something that’s reality-shaped but not actually reality.
And trust me, I get it. I’ve had my own struggles with expecting life to look like various moments from fiction and not understanding why it didn’t. And I’ll be real with you: that started fading a hell of a lot faster when I went back and looked at those stories and realized how much I missed and misunderstood them.
(Looking at you, St. Elmo’s Fire…)
But here’s the thing: the confusion, even the anger is understandable… it’s just a little misplaced. The reason why this is so upsetting is because of what it suggests: that there’s something you missed. That this was always possible, and there’s now that niggling question, that quiet voice in the back of your mind that says “… wait, is this my fault?”
To be perfectly frank: yeah, there were things you missed or misunderstood. I’ll break a lot of it down for you, but I’m going to give you the real takeaway that you need: it’s ok. You may have not learned some lessons when you were younger, but you can learn them now and that’s a good thing. It’s no less meaningful just because you’re 27 instead of 17. If anything, you’re better positioned, because you’re more established and more stable, with a better foundation for your life than the ball of hormones and angst that you were back then.
Part of the problem is one of perspective. This is something that comes up a lot, especially for people with backgrounds and experiences like yours: you’re comparing the unedited footage of your lived experiences to other people’s highlight reels. You’re making a lot of assumptions about other people’s lives and experiences based on extremely limited and inaccurate information.
I want you to pay attention to the words you used in describing this: “I’ve watched others move through relationships, dating, marriages, and everything in between with what seems like very little effort,” and “it feels as simple as showing up to a party or hobby group and effortlessly meeting someone new.” (Emphasis added by me). The operative words here are “seems” and “feels”, which is precisely the issue: this is what it looks like when you only see a very small portion of what was going on.
It’s no different than watching an athlete or artist in the height of their powers, doing incredible things with such ease and aplomb that it seems like it’s the simplest thing in the world. But what you’re not seeing is all the work that went into getting to that stage, all the struggle, practice, failed attempts, developmental stages, plateaus, frustrations and more practice. Jack Kirby didn’t come out of the womb able to draw dynamic superheroes that would change the medium as we know it, any more than Michael Jordan or LeBron James were born able to sink threes and run rings around their opponents. It was a lifetime of practice and implementation that got them to the point that everything looked easy and effortless.
All of those people who seemed to have no problem meeting, dating and mating? They all had to learn, they all struggled, they all had to put in practice. You didn’t see the awkward stages, you weren’t around for the failures or the fuckups. They may have started earlier and they may have been fortunate to be in circumstances that supported their development more readily than you had, but they all had to put in the work and learn how to apply it.
Similarly, the parts you saw were not the end point of those relationships, and often not even the beginning. You didn’t see the rough parts, you weren’t there to hear the arguments or the mistakes and conflicts. You are extrapolating based not on experience or observed reality, but on imagination and – importantly – imagination that serves to confirm your worst fears.
And a big part of what you’re missing is intent and deliberate effort. This is another recurring issue with folks who are in a similar situation as yours, something I addressed in a very recent column: none of those relationships “just happened”. Every one of them happened because someone took the initiative, who went out of their way to connect and to stay connected. Everything that “happened naturally” happened because two people were putting in the work of becoming friends or lovers and being involved in each other’s lives. They didn’t get pulled together by social magnetism or tectonic forces, they had to make offers of connection, to reach out and connect and keep in contact.
Every relationship, platonic or otherwise, is built on a foundation of deliberate effort and connection. It starts with simply getting to know one another, finding things you have in common through conversation, seeing if they’re even your people or you’re theirs. If you are, then the building is erected through a process of firming up those connections through interactions – conversations, sharing experiences, building rapport and mutual interest, respect and interaction. That, in turn, makes it much easier to get together and do things to encourage bonding and sharing – invitations to go grab a beer or see a movie or hang out. By the time people get to the parts that you saw – those seemingly effortless moments of connection – you’re watching the placement of the capstone.
I bring this all up because you have been handed an opportunity here. You are being shown that your belief that you’re inherently undesirable and unlovable is incorrect, so now the question is “what will you do with this information”. You have the choice to keep looking backwards, or to move forwards. You can take this opportunity to motivate you to go out and start building your social skills, learning how to connect with people and build friendships and more. Or you can keep looking back at the past, which will only serve to root you down and keep you there.
Yeah, life might’ve been different if this had come to you when you were younger. But it’s here now. This is your chance to move beyond your past, to build something new and wonderful, as long as you’re willing to forgive yourself for what you missed out on and let it be in your past.
That’s up to you. But I think you should take this as proof that you were wrong about this particular self-limiting belief… so maybe you’re wrong about the others as well. And if that’s the case… well, imagine what you can accomplish now that you couldn’t before.
That sounds pretty damn good to me. So just ask yourself one important question: how do you want to do this?
Good luck.
