Contra Cyn on Asking People Out
My friend Cyn has written a post disagreeing with me on whether women should ask men out. Her main points are ones I’ve heard many times before. Read the whole thing if you want the full argument, but here’s the one-sentence summary of each:
Asking men out filters for men who are passive and/or don’t really like you
The wrong initial approach can doom a relationship
Not every relationship starts with an “ask out” moment
Point 3 is the easiest to address. If you manage to get into a relationship without anyone doing any asking out, that’s great! You do not need to ask anyone out unless you’d like an additional relationship. My advice to ask people out is only for those seeking relationships or other romantic and/or sexual connections. If it “just happens” for you, that’s wonderful, but it is not the common experience. Usually someone has to take the initiative.
Point 2 is baffling to me. I know everyone likes a good meet-cute story, but it really doesn’t matter. If you find yourself on a date, then congratulations! Your strategy was successful! As long as you didn’t do it in a way that was deceptive or otherwise going to cause problems later, it doesn’t really matter how it happened. The date is where you do the actual discovery about the other person. If the date goes well, neither person is going to care how it came about. I know there’s a persistent myth that the wrong approach can poison the whole relationship, but I don’t know where it comes from or why anyone would think that.
Your Filter is Broken
Point 1 is the real issue. It’s true that if you ask people out, you’re giving up a filter, though I doubt it’s a particularly valuable one. It’s true that there will be some correlation between a person’s willingness to ask you out and how much they like you, but it’s a pretty weak correlation.
First off, you’re not really filtering for men who like you. You’re mostly filtering for men who ask out a lot of women, like Brangus:
At one point, not that long ago, I was asked to speak on a panel for people with body counts over one hundred. At one point I was asked some question I don’t remember, but I asked all of the women in the room to raise their hand if I had ever hit on them. Approximately every woman I had ever met before that day raised their arm.
Brangus is great! But when he asks you out, it is not an indication that you are a unique, special snowflake. As he says, you “play the numbers.”
But more importantly, there are a lot of reasons a person might decline to ask someone out. In fact, Cyn gives several in her post! It’s ironic that she lists all of her reasons why she doesn’t ask men out, but assumes that a man who doesn’t ask her out simply isn’t that interested. And that is, of course, because she doesn’t directly address the elephant in the room: gender essentialism.
The Filter Cuts Both Ways
Cyn claims that if women ask men out, they will often end up with men who are passive, cowardly, or don’t like them very much. But that’s a symmetric problem. If it’s true, then if men ask women out, they will often end up with women who are passive, cowardly, or don’t like them very much. Thankfully, I don’t believe that either is true.
Cyn’s reasoning rests on the assumption that a man who likes a woman will ask her out, but a woman who likes a man simply pines in silence (or gives a few subtle-but-deniable hints so she can tell herself she’s being “yin” which is ~totally different~ from being passive1). But, of course, that’s ridiculous. It’s not the 1950’s anymore. Women can and do ask men out all the time, and very large numbers of men are reasonably apprehensive about expressing sexual interest outside of dating apps ever since doing so imperfectly got declared a reason to socially shun someone. Aside from that, there are still many reasons why a man might not ask a woman on a date despite being interested. In the modern world, in-person asking is no longer the norm.
A First Date Doesn’t Imply a Second
Cyn claims that she used to ask men out, but she ended up with a string of men who said “yes” but weren’t particularly interested in her. But the relationship persisted because they were too passive to break up with her. I notice I’m confused. She yada-yada’d the important part! How did she go from asking a man on a date to being in a relationship with him that would necessitate a difficult breakup? That’s the part of the process to address.
I want to be clear about something: I’m only advocating asking people on dates. Asking a person on a date in no way obligates you to start a relationship with them or to be the only one taking an active role. If you go on a date and your date doesn’t seem that interested in you, just don’t go on a second. Finding out how you relate to each other is what the date is for!
Courage is a Virtue
I’ve read dozens of defenses arguing why it’s Right and Good that women rely on subtle signals instead of just asking, and they almost always strike me as cope. The real reason is pretty obvious: cowardice. Asking people out is hard. It requires vulnerability, agency, and courage. It can make things awkward. It can lose you status. People (men and women) who don’t have to do it to get dates mostly don’t, despite the fact that they would probably have better outcomes if they did. It’s uncomfortable, and people tend to stay in their comfort zones if they can.
There is one exception: being passive is a strategic move for women who are very into traditional gender roles. While the overwhelming majority of men are fine with being approached, there is a certain type that will be off-put by it. If you’re looking for a relationship that reflects midcentury gender roles, it’s best to stick to those roles. Of course, if you’re reading this blog, it’s very unlikely that you actually want that.
So my advice for both men and women remains: if you like someone, ask them on a date. Don’t play silly games where you send subtle signals and hope they’ll pick up on them. Don’t try to do too much filtering before your first date. If someone is available and you think you’d enjoy a date with them, that’s all the filtering you need. Do the real evaluation on the date.
What Is the Actual Disagreement Here?
This is what Cyn describes as “not asking men out”:
My current relationship started like this: we were introduced at a party. We talked. I asked if he wanted to find a quieter room upstairs to keep talking. We did. He initiated a kiss. After that there wasn’t really an official “ask out” - we just texted, we knew we liked each other, and things progressed from there.
10/10 no notes. Though that seems pretty yang for a person who describes her approach as yin. By my scorecard, asking to go find a quieter room is the functional equivalent of asking a person on a date. It’s like asking someone up for coffee, so I’m not even sure we disagree. You don’t literally have to say the words “do you want to go on a date with me?”
The point is to take responsibility for things happening. You don’t “set the table” and wait for the other person to act. If things aren’t where you want them, you act to make them different.
Sometimes You Don’t Know
My advice to ask people out is for situations where you want to go on a date with someone. Cyn makes the point that attraction for women is often reactive. A man being very into a woman can make her more attracted to him. As with most things phrased in gendered terms, it applies to both men and women. And that’s fine! If you don’t know if you would enjoy a date with someone, then it’s perfectly reasonable not to ask them on a date. Personally, I ask very few people on dates because it’s rare for me to meet someone I like. But when I do like someone, I ask her out (and you should too).
But sometimes you don’t know how you feel about someone, but an expression of interest can push them over the line.
Human romantic preferences aren’t static rankings. They’re more like differential equations - functions that include a term for how much the other person likes us.
If you genuinely don’t know how you feel about someone, I lean toward just asking them out and seeing what happens. But if you’re truly on the fence, it’s also fine to wait for them to take the initiative. If their interest and enthusiasm could push you over the edge from “no” to “yes,” then it’s the right move to wait for them to show it.
UPDATE (1/30/26):
Sympathetic Opposition has written a post agreeing with Cyn and disagreeing with my position. She goes into a number of reasons why the stable marriage problem is different from real life, all valid. It convincingly argues that women looking for marriage need to be choosier than men, largely because of biological realities. But the main point of the article is the same as Cyn’s - that who does the asking is an important filter.
She also goes through a number of circumstances where it does make sense for a woman to ask men out. The key paragraph is this one:
You should expect asking a man out to be more likely to work if you have lower transaction costs: if it’s easier for you to date multiple people at once, easier for you to break up with people, if you rarely get hung up on a man.
These are not personality traits. You are not born with them. These are skills that you can develop. I know because I had to develop them! In my adolescence, much like most boys, the idea of asking a woman out was terrifying. It was equally terrifying to reject a woman who expressed interest. The transaction costs of starting or ending a relationship were huge. The solution was courage.
As I grew up, I had to learn that a woman accepting a date wasn’t a reliable indicator of her interest. I had to learn how to tell if a relationship was developing in a direction I liked, and how to end a relationship early if it wasn’t. I had to learn how not to idealize a woman just because we were dating, and not to get tunnel vision. Women can learn these skills too! And the ones who do typically have more success, or at least avoid the failure mode where they get “stuck” in a relationship with an unsuitable partner.
The “women are just being yin” argument profoundly bothers me because it’s designed to flatter women without challenging them. All the things it describes (sitting near someone, laughing at jokes, finding excuses to touch, maintaining plausible deniability) are the same things cowardly men do when they’re too scared to ask a woman on a date. The whole argument is just status-quo apologetics.