Why I Stopped Asking Men Out (Even Though the Math Said I Should)

This is a response to Ajeya Cotra’s “The Stable Marriage Problem” and Wesley Fenza’s “Just Ask People Out (Now with Math).” I’m the friend Wesley cites as introducing him to this framework. I used to believe this math. I tried it. Here’s what I learned about why the model breaks down.

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As a mathy, feminist teenager, I was exposed to the secretary problem and the Gale-Shapley stable matching algorithm, and my little brain was SO EXCITED. I was a romantic, deeply hoping for my ideal mate, but I also wanted to reject gender norms and live authentically in a world of true sexual equality. My eyes bugged out of my head when I saw the implications: if I ask men out more, I can get the best man! My girl friends who wait around to be asked will end up with a female-pessimal outcome!

What I didn’t anticipate: I ended up with a string of “eh, I don’t REALLY like her, but she’s OK, and I’d rather have Any Woman than be alone” men. Men too passive to break up with me, leaving ME to end things despite being the one who asked them out in the first place.

It’s uncomfortable to break up with people you asked out. You have to wrestle with the fact that you made a Bad Decision - sometimes several in a row. Worse, the method itself selected for exactly what I didn’t want. By doing all the initiating, I was screening for men who would let me do all the initiating. The dynamic of male-passivity got set at the start and never really changed. I didn’t like feeling replaceable.

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Let me explain why the math doesn’t transfer to real dating the way Ajeya and Wesley think it does.

The Secretary Problem

The secretary problem assumes you’re the only decision-maker, evaluating a parade of candidates who have no preferences about you. You observe, you judge, you accept or reject.

Dating has a second agent with preferences. The “secretaries” can reject you. And here’s the kicker: their interest in you is partly a function of how you approach them. The algorithm breaks the moment you introduce someone who can say no - and whose enthusiasm might depend on whether they had to work for your attention.

(There are other issues too - we don’t know the pool size, we can revisit past options, preferences change - but the fundamental break is that dating has two decision-makers, not one.)

The secretary problem might apply to auction theory, where you’re evaluating bids on a single legible dimension (price). It applies very poorly to romance.

The Stable Matching Problem

Gale-Shapley can give us some insight, but both Ajeya and Wes draw too much from it by assuming it matches reality more closely than it does.

I agree the algorithm incentivizes agency. I disagree that agency must mean “asking people out, directly, visibly, legibly.”

The main place Gale-Shapley diverges from real life: in the algorithm, Alice ranks Bob a 7 and that never changes. In real life, Alice might rank Bob a 5 initially, but if Bob shows genuine enthusiasm and effort, he becomes a 7. If Alice has to do all the pursuing and Bob just passively accepts, he stays a 5 or drops to a 3.

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. Real attraction can spiral upward into joy and love, or spiral downward into resentment and feeling taken for granted. The math assumes static preferences; real attraction is dynamic.

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Jacob Falkovich’s essay “Navigation by Moonlight” is one of the best explanations I’ve seen of how women can exhibit agency in a way that, to the more mathy and rational among us, seems invisible and passive.

He distinguishes between “yang” agency (direct pursuit, explicit asks) and “yin” agency (receptivity, creating contexts, subtle signaling). What looks passive is often highly strategic - setting the table for the outcome you want while letting the other person take the visible final step.

During college, in my “just ask men out! It’s the feminist thing to do! I’ll get better partners!” phase, I asked out a decent number of smart, high-status, seemingly interesting and kind men. But I couldn’t know before dating them how they would interact with a partner. Were they doting, thoughtful, generous? I didn’t need a LOT, but the dynamics we established at the start set the stage for relationships that didn’t feel sustainable.

So I shifted. Rather than overtly asking out men I liked, I started sending classic signals that were well-understood as flirts and expressions of interest, putting the ball in their court. Asking to dance together at a party. Choosing to sit next to them. Laughing at their jokes. Finding excuses to physically touch. Comparing hand sizes. You know the drill.

This fans the flame of desire while making it clear that, for the invitation to be accepted, they have to conquer a bit of fear. Be a little public. Be Agentic - which is a trait I (and I expect many straight-leaning women) find desirable in a partner.

This isn’t passivity. It’s a form of agency that also gathers information. If he can’t or won’t take the final step after I’ve made it abundantly clear I’m interested, that tells me something important about what a relationship with him would look like.

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A note on women dating women

Everything I’ve said so far assumes a man-woman dynamic with its culturally baked-in scripts. Women dating women face a different problem: there IS no default script. When both people are used to signaling and waiting for the other to make the visible move, you get the “useless lesbian” meme - two women who like each other, both waiting, neither escalating.

In wlw contexts, I think more direct asking actually IS necessary, because subtle signals are much more likely to be misread or missed entirely. When there’s no shared expectation of who moves first, someone has to break the stalemate. The yin approach works when you’re playing off a yang counterpart; it works less well when you’re both defaulting to yin.

So if you’re a woman dating women: the math might actually apply better to you. Sorry.

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”Asking out” is too simple a frame anyway

The more I think about this, the more I realize that “A asks out B” is a weirdly reductive way to describe how relationships actually start. Most of my relationships haven’t had a clear “ask out” moment at all.

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.

So who was the “asker”? I created the context (suggesting we go somewhere private). He took the visible romantic risk (the kiss). From there it was mutual. This is how most relationships actually unfold - a series of small escalations where both people take turns being brave. Not one person boldly asking and another passively accepting.

The Gale-Shapley framing of “proposer” vs “receiver” flattens all this into a single binary moment. Real courtship is more like a dance - back and forth, each person testing whether the other will match their energy.

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I want to address two audiences directly.

**To women feeling pressure to ask men out to be “agentic”:**You can be agentic without doing the stereotypical “Do you want to go out with me?” Flirting IS doing something. Creating opportunities IS doing something. If asking men out directly has worked for you, great. But if it hasn’t, or if you’ve felt weird pressure to do something that doesn’t feel right, trust that instinct. There’s more than one way to go after what you want.

**To people like Wes who see women’s reluctance to ask out men as a moral or strategic failing:** As long as women are yinning and not truly being passive, they’re being smart, not self-sabotaging. The math doesn’t prove what you think it proves. Before judging women who don’t ask men out, consider that they might be running a different algorithm - one that’s testing for exactly the traits they want in a partner.

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I want to be clear: I haven’t embraced traditional femininity wholesale. I still cold-email about opportunities, I still advocate for myself at work, I still initiate in plenty of contexts. But I’ve learned that different strategies work in different environments. The “optimal” strategy in a hypothetical sex-blind, perfectly egalitarian world may not be optimal for the world we actually live in.

I’m also not saying “never ask men out.” Some men are too in their heads to recognize yin signaling as a bid for their attention. Some contexts make direct asking the obviously correct move. But I do want to offer women permission to try a different path - one that’s not about passivity, but about testing for reciprocal effort from the start.

In the end, it all adds up to normalcy.