33 Comments

I appreciated this Ozy, thank you! I feel significantly more prepared to Ask Someone Out.

To be honest I am still stuck at the stage of Find Someone I Like Enough To Ask Out, but that's a different problem 😅

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What do your friend groups and event calendar look like? Shifting that could help you

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I will say as a dude in his 30's, not asking people out was the single thing that most hurt my romantic life, and I found a partner very soon after I figured out how to overcome my anxiety and actually do it.

One phenomenen I've especially noticed is that certain men who are trying to be progressive think that asking women out is somehow "unfeminist" and they should feel guilty about it. I'm sure you can find feminists who think that, but on the whole they are just concerned about the whole harassment thing that you detailed here, not on people who politely ask others out and take no for an answer.

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You want to laugh, I basically avoided any women who gave off any signs of left-wing politics at all for a very long time because I figured any mistake would be met with a harassment accusation. At least, I figured, a nonfeminist woman would see me as a human being who made a mistake rather than an enemy.

I kept finding women who were interested in me turned out to be feminists, and then wanting out but being terrified of what they would do to me if I broke up with them.

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this really helped me really drive through my brain that i don't want to date people that don't want me. I would have thought that it would be obvious to myself, but after being really embarrassingly rejected recently, and still wanting to pursue said guy, i realize now that it would be terrible if i actually ended up with him!!

It also doesn't help as a trans gay man that many people still view me as a woman, but that just helps me filter out the dating pool even more, right? i want to remain optimistic about this (´・ᴗ・ ` )

thank you very much for writing and sharing with us!!!

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one trick I have found useful for scary conversations:

1. isolate some extremely short, non-scary prefix of the conversation, like "hi" or perhaps "hi, I'd like to ask you something"

2. form an intention to do 1 (you can't do it yet, because it's scary, but get attached to the idea anyway)

3. deliberately distance yourself mentally from the reason why you wanted to do 1, while keeping the intention to do it

4. do 1, it's not scary because you're not thinking about why you're doing it

5. remember why you're doing it

6. oh no! it's now *more* awkward to back out of the conversation than to just continue with the scary part

7. congratulations you did it

(I phrase this sort of facetiously but it really works on me)

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one part of this post I want to emphasise and generalise is that IMO awkward conversations are much less bad than people seem to think? like, not only dating but other stuff like talking to your friend about their one habit that you find difficult -- it's gonna be weird and you're gonna stumble over it, and have to do a bunch of clarifying and misunderstanding and fixing misunderstandings, but like, generally you *will* get there, and as you say, in the cases that matter most both people *want* to get there, so once you've muddled through the embarrassing mess of words you'll often find out that you have actually ended up where you wanted to be?

so, next time your hindbrain says "we can't say that, it'd be awkward", at least ask the question "so what?"

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> as long as you’re steering clear of professional contexts and not hitting on teenagers while an adult—it doesn’t cause serious harm.

I expect that, to people without much of a social life (who I expect are a significant part of your intended audience here), the "steering clear of professional contexts" part makes this much more difficult: "professional contexts" may be the only place where such people already interact with other people in person enough to become acquainted with them (if they are no longer in school), & thus the main place where they might have an opportunity to Ask Someone Out who they know something about rather than a complete stranger. Therefore the message this post may send to a person in that situation is not 'you should ask people out' in general, but rather 'you should not ask anyone out without first either becoming socially brave enough to ask out complete strangers or developing a substantial nonromantic friend group to select from, because asking those people out with whom you are already acquainted is socially unacceptable.'

(Since I have literally zero personal experience in this area, it is likely that I am missing something important that partly or entirely obviates this problem, but I thought this comment worth posting anyway in case that is not the case. It would also be entirely reasonable for you to say that someone in the situation I describe has bigger problems that they should fix before even seriously thinking about asking someone out.)

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Yeah, it's a hard problem!

To be clear, there are *plenty* of professional contexts where it's fine to hit on people. But I do think it's possible for a well-intentioned but socially unaware person to cause actual harm hitting on people in a professional context, in a way that just is never going to happen if you hit on people at a book group.

But ultimately if you're in that situation you have to go on The Apps, meet people outside of a professional context, or learn to read signals well enough that you can be confident no one thinks their job depends on saying 'yes' to your advances.

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Right. I went on the Apps.

The thing you're also forgetting is that if you shoot your shot and miss at a book group (or board game club), you now have to avoid that person for the rest of the time to avoid awkwardness or being seen as 'pushy'.

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If a person has absolutely no interaction with people outside of work, I do think they need to fix that problem before dating.

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This is going to sound like a very stupid question, but this reads like the post of a person who is OK with stupid questions. What is the difference between asking someone out in the sense that this post is talking about versus just inviting someone to hang out/get coffee together/whatever? Should you only ask someone out if you have “special feelings” for them? Should you only ask someone out if you think you might be able to have romantic interest in them? Will a person being asked out think this means you might want to have sex at some point? Where does kink fit in?

Also, great post, thanks, gonna be thinking about this one.

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Asking people out on a date isn't very different from asking someone to hang out-- in fact, I have occasionally gone to hang out with someone unsure whether it was a date or not.

My suggested script includes "you're cute" because this is a compliment that you're generally not going to give a platonic friend,* and so it establishes right away that this is on a dating footing. In addition to physical appearance compliments, dates generally involve more physical touching: you begin with normal touch (like touching them on the shoulder for emphasis), wait for them to reciprocate, and if they do gradually escalate to kinds of touch that people don't do in platonic relationships (such as handholding or putting your head on their shoulder). Dates also often have more conversation about future plans-- things like kids or career plans-- because people are trying to learn whether the other person has any obvious dealbreakers.

You can also just ask whether it's a date! Script: "um, this is kind of awkward, but I can't figure out if this is a date or not?" Once they're already hanging out with you, they're not going to be mad at you, even if it is transiently awkward.

If an orientationally appropriate person invites you into their bedroom without providing a clear reason ("my xbox is there"), they are usually subtly attempting to initiate something between makeouts and sex. If you don't want it, don't make a big deal about it, just say "nah." (This is also a good way to initiate sex, but you generally shouldn't do it unless you've already held their hand or put your head on their shoulder or kissed.)

In general, people who are dating assume that sex is on the table. If you're uninterested in sex (which is what I got from your comment), it's usually a good idea to bring this up in the first few dates. Don't explicitly say "I don't want to have sex with you"-- people tend to find that hurtful. Bring up your reason naturally in conversation: for example, if you're talking about religion, you might say "my faith is very important to me, so I don't want to have sex before marriage"; if you're sharing funny memes, you might show them a meme about being asexual and say you find it relatable.

Often, people don't talk about kink until after they've had sex for the first time. (I agree this is very silly.) It is generally acceptable to talk about kinks in private after you've had sex for the first time. Otherwise, you generally shouldn't bring up kink (or any sexual topic) totally out of the blue, but you can bring it up if it seems like a natural way to continue the conversation. Unfortunately all the natural ways *I* have to bring up kink are very Bay-Area-specific ("I'm looking forward to Folsom this year!") and I don't know how everyone else does it. >.>

*Sometimes women platonically call each other cute, which is one reason that lesbian sheep syndrome is so common!

**Unless you're a man on a date with a man, in which case go wild.

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It really depends on the group what's platonic or not: in my little corner of ace space and mostly autistic sensory-seekers, if someone's openly cuddly you can absolutely ask them about holding hands and putting your head on their shoulder and many more things. But that's a very little corner of the world.

Platonic cuddle piles are a wonderful thing.

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I've never been to the Bay Area, but 10-15 years ago you would leave 'Secretary' in your list of movies on your OKCupid profile. ;)

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> you begin with normal touch (like touching them on the shoulder for emphasis), wait for them to reciprocate, and if they do gradually escalate to kinds of touch that people don't do in platonic relationships (such as handholding or putting your head on their shoulder).

I could definitely benefit from a whole post about this, or a link to someone else who has talked about it. I can't remember any times when I've touched a friend/acquaintance on the shoulder for emphasis, or when anyone has done that to me; the same goes for other platonic physical touch. I always feel like I should initiate some kind of touch on a first date, but I have no idea what or how and end up never touching my date at all. (I can't tell if this is contributing to my first dates all being uninterested in second dates.)

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> A lot of straight men assume that straight women are constantly turning down suitors. This isn't true.

The modal straight woman isn't, but people's preferences are correlated in the real world, and chances are that if you're interested in a woman, she's one with a lot of suitors. This is especially true of women whose interests and personalities put them in predominantly male social circles (or make them particularly appealing to certain kinds of otherwise-picky men). And from listening to what women I'm interested in say about dating, it does sound like they're fending men off pretty often.

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Ozy’s advice is still great in those cases, IMO! Most “fending off” effort is about dealing with latching-on behavior where you haven’t been asked out - you know someone is interested in you and you’re not interested in them, and things are awkward because you like having them in your life (or at least you like being in the place they frequent too) but you don’t want them to slide into a romantic way of relating to you, and it’s gauche/socially risky to say “I don’t want to date you” if it’s plausibly deniable that they’re interested. Being asked out directly in that case is a gift! You can cut back on the amount of calculus you have to do about how friendly you can be without it being interpreted as reciprocating sexual interest, and it’s easier to go on being friends/teammates/whatever. And the asker can move on - it’s win/win.

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20hEdited

I'm sorry, this is positive and pleasant and all, but you really easily dismiss the prevalence of "batshit" people and their influence. I've had a women ask ME out and a batshit third party intervened because as an unattended male I MUST have been up to no good.

Also, this leaves out the part where people say yes to a date, then flake, because it's easier than saying no, and this happens with such universal regularity you wind up a wreck that doesn't believe the things people say anymore.

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I think you have to do a realistic risk calculus. What is the harm a batshit person can do to you? If you’re behaving decently and staying away from well known danger areas like dating a coworker, student, or much-younger woman, most likely the risk here is « crazy people disapprove of you, » not anything really dangerous.

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Yeah. I agree with this. I'm somehow happily married and I was basically one of these guys. If I read this then, this would have not convinced me, and it's primarily the "batshit" problem. If it was just them that was batshit I'd probably say that's fine if uncomfortable and deal with it after asking her out and getting shot down. But part of being batshit is spreading your batshittery to your friends, who are probably also acquainted with you, the asking her out guy. And batshit people tend to be quite good at convincing normies that they're not the problem, the evil man who dared presume I like them and ask me out, is the actual problem. And this can snowball very quickly and destroy your standing in a social group (a social group that you, as an awkward guy, probably value quite highly because when you're awkward it's often quite tough to replace a social scene).

2010's feminism was really rough on guys in this dynamic, and I have a very hard time getting too upset at them for voicing this.

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In that situation, the correct response is to not care about the batshit third party?

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From a straight male perspective -- The online ratio of women complaining about excess male attention, to women complaining about insufficient male attention, seems fairly high.

I do remember seeing a twitter poll which found that men tended to think that women wanted more male attention, but in actuality, women were more likely to want *less* male attention. Unfortunately I can't find it right now.

I think it's plausible that your readers should be asking more people out on their current margin. But I think you're presenting this as a bit too much of a one-sided tradeoff. I think women don't like turning men down. For example, I sometimes notice what feels like pre-emptive frostiness to ward off me asking them out. (Naturally, I don't ask them out at that point.)

Don't forget the abundant online dating matches that almost all women have access to. And of course, the high prevalence of ghosting is an important revealed preference fact. (I used to ask a lot of women for their numbers. Generally I would have a friendly positive-seeming interaction, then just get silence when I texted her later.)

If women really want us to ask more, they should say so, and they mostly aren't saying so.

I think the actually-useful guide here would be a guide on how to figure out the difference between a woman who's experiencing some social anxiety because she thinks you're attractive, vs a woman who wants you to go away, but doesn't want to cause conflict by saying it directly.

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I couldn't write that guide, because I always just shoot my shot.

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So the cynical view here would be that you are actually annoying people and they are just too polite to say so.

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Perhaps this is true! I think it is justified consequentially though.

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also though, straight / bisexual women, please do ask men out if you like them. that nice feeling you get when someone you like flatters you, even if you're not ultimately into them? men reportedly also like that feeling

see also https://eudai.substack.com/p/the-odds-are-good-and-the-goods-are

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Genuine question, Ozy -- surely someone who needs to be told things like "don't open with 'nice ass btw'" is absolutely NGMI? Are there any real people at the margins for whom this is going to be novel, course-correcting advice who is also not irreversibly under the threshold for social functionality?

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I don't know, a lot of guys have absolutely no idea how to approach, especially these days. Your choices for models are some guy in a PC/woke movie where the girl does all the work and Andrew Tate.

So, it may be helpful.

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One thing I want to disagree with you on -- depending on context, if someone says no, I would say that it might be OK to make a quick confirmation of that. This doesn't really apply using your script, because it proposes no specific time or activity and is pretty overt about it being intended as a date. But not everyone is going to do things that way. Now, if you ask someone on a date, and they're interested in that but not in the particular activity you suggested, what they *should* do is make a counter-offer... but I have heard of people failing to do that! So in such a case I don't think it's so bad to quickly suggest an alternative to be sure. I guess this does require the social skill of being able to ask in a way that makes it clear it's a quick ask for confirmation -- the sort you willl *definitely* not continue past -- and not, like, you starting from scratch, which would be obnoxious. I suppose when you consider Ozy's target audience with this post (see the bits about asking out coworkers), maybe the people reading this actually shouldn't do that after all. :P Still, thought it was worth noting...

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Obviously I think this is good pushback against the batshit people you speak of, but I think it's worth taking a moment to go further and say *why* so many people are convinced by these batshit people. Remember, if someone believes P and you want to convince them of Q which contradicts P, it's not enough to argue for Q; you have to explicitly say "not P"!

So, to do that real quick -- a lot of people are convinced by these "batshit" people because such people don't present themselves as batshit. They present themselves as normal and reasonable and good feminists. And those fooled by them lack the social experience to realize that this is not the case. So they expect *everyone* to act as the batshit people describe, and for this to be normal and reasonable and to be considered normal and reasonable, and if you disagree you're a sexist and nobody will listen to anything you have to say.

So, while you are basically already saying this (we definitely don't disagree on this point), I want to also say more explicitly: No, these people are batshit. What they describe as normal is not normal, and is not how most people will act. Most people are reasonable, and reasonable does not mean what the batshit people are describing as reasonable -- it means what you already know as reasonable from more general social interaction. Stop listening to these people and judge right and wrong for yourself instead (yeah OK that's a hard transition to make but you will have to). But you already know what reasonability actually looks like, so apply that!

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This is really good advice. Only thing I’ll add: people don’t respect you less or think badly of you in any way because you asked them out even if they say no, as long as you do it respectfully. You’re really risking much less than you think in most circumstances. And if you’re really that worried, just talk to her more to try and figure out if she likes you or not. It’s not that hard, trust your instincts.

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My mom used to say: “you can always ask a woman out. It either gives her the joy of saying yes and feeling flattered, or saying no and feeling flattered”.

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