The Odds are Good & the Goods are Great

Women looking for partners should initiate more

i. the odds are good

I want to urgently hammer into the consciousness of every progressive American straight woman struggling to find a partner that they should ask people out.

I have long been distressed by the reports of women with unhappy dating lives coming in from my direct social circle and the broader US culture, and my hunch is that this is one of the key factors separating their experiences from mine. I have never been on a bad date. I have never had sex I felt coerced into. I have also asked people out five times more often than I’ve been asked out, and I don’t think this is coincidence.

(Concretely: I’ve asked 12~15 people for dating or sex, and been hit on 2~3 times. This is over 7 years of romantic and sexual activity. My M.O. is to email someone, tell them what I like about them, and invite them to coffee or cuddle with the possibility of sex.)

My suspicion is that the majority of my women friends who had bad relationships had partners who chose them, rather than the other way around. If you are 100% passive in the dating market, your partners will be drawn from the set of ‘the kind of people who wants to date you’. If you are 100% active, your partners will be drawn from the set of ‘the kind of person you want to date’.

There are a variety of men in the world, ranging from “asks out one person a year – the person they are most interested in” to “asks out one person a week based on weak interest”. There are many more men in the former category than the latter. Asking people out is hard, so it’s a minority of people who make it a habit – but the latter type will be highly represented in the set of people who ask you out.

So, while it would be great to be on a date with a guy who asked me out because I’m the most spectacular person he’s met this year and he thinks about me all the time and has been beating down thoughts of what to name our children… statistically the guys who ask me out will tend to be my acquaintance who thinks it’s worth a shot and tries it out after a cumulative hour of waffling. A relationship with the first guy has a better chance of going well than a relationship with the second guy, although of course it’s nonzero for both.

But I argue that your chances are even better if you date the guy you think is the most spectacular person you’ve met this year. US progressive culture is in a weird place right now where women are socially permitted to initiate but they don’t seem to quite believe it yet. As a consequence, the dating field for the minority of initiating women is highly profitable.

Here’s a mathy, theoretical proof backing my intuition that initiating is favorable. Simulations of the Gale-Shapley matching algorithm, in which one group of people (e.g. hospitals) reach out to their favorite picks (e.g. medical students) who then accept or reject coming offers, the proposers have their preferences met to a greater degree than the accepters. I’ll quote this short Cornell course blog post in its almost-entirety:

Originally, the matching algorithm was designed so that hospital residencies were the proposers. As a result, residencies always received students who were among their top picks, but medical students applying to the residency programs were often paired with residencies that were not ranked highly on their preference list.

…

A recruiter for a company can passively post a job listing and choose from the candidates who apply, or the recruiter can reach out and contact the best talents in the field to try to recruit one of them. If the recruiter is trying to find the best candidate he possibly can, he is much better off pursuing the latter strategy. Although this requires more effort on the recruiter’s part and involves the risk of rejection, the recruiter may actually find the top talent in the field, because he is actually going after them, instead of hoping for them to come to him. The same principle applies to finding marriage partners, going after (or not) one’s dream job or career, and applying to universities. It turns out that the best strategy to win your top choice in any two-sided market is to take the initiative and actively pursue it.

<But that’s kind of a weird thing to do. He or my social circle might judge me.> Okay, maybe. I’ve been in liberal American social environments my entire adulthood, I can’t say what’s right for you. I’ve personally never perceived negative consequences for my promiscuity. If you’re in a progressive social circle that buys into the ideal that women should be able to do anything men can do without social punishment, shrug it off when people bring it up – “Why shouldn’t I? You wouldn’t be bringing this up to a guy, would you?” If you’re not in an environment where this will work, this blog post is probably useless to you.

<It’s much nicer when someone asks me out. That way I know that they’re interested, and aren’t just going on a date with me because I asked.> Yeah. But… they feel that way too. That warmth of confidence and chosenness you feel in someone when you’re on a date they asked you to? They’ll feel it too. Being asked on a date is not a situation that’s going to make them feel neutral or judgmental or disinterested-but-I-have-nothing-better-to-do-with-my-evening.

ii. the goods are great

An entirely separate point I want to fan gently in front of your foveal vision is that you might consider going after my dating pool of educated, nerdy, shy engineer types. If you are the right type of person, this will work out well for you. Read on to figure out if this is suitable advice.

Educated American women are numerically overtaking educated American men, and the news says they’re having trouble finding equally educated partners with similar earning potential. For years I’ve had trouble squaring this with my dating life in the past five years in two different tech cities, which is that I

• meet a really nice, smart, kind of awkward guy earning ~50% more than I do (usually due to being further along in a tech career than I am)

• ask him on a date

• have fantastic sex in between debating modern history, biology, philosophy, etc

• later listen to him tell me, “I’m so glad you asked me out. This never happens to me, and we’ve been having such a great time.”

After the first five times I’ve stopped going WHAT DO YOU MEAN THIS NEVER HAPPENS TO YOU? and started accepting this as a mysterious pattern in the dating world.

If you share my taste for this kind of guy (shy, well-read, awkward, logical), or can get yourself to share it, you can also get into this ludicrously undertapped market of smart, high-earning men. If they’re not to your liking, ah well. But if they might be – try them out.

I think my advice is better for

• Educated women in tech hubs

• Women who like reading stuff online and are capable of crushing on people based on their writing (my favorite dates have been after asking out bloggers)

• Women in STEM

• Women who are okay at, or prefer, blunt communication

• Women in progressive social circles

• Women who aren't put off by guys with kind of dorky faces who dress badly. I love ‘em but everyone filters on looks to some extent and it's fine to bounce off for whatever reason

iii. questions and counterarguments

Putting this photo here just because I want a beautiful painting to show up in the header. It’s by Samantha Keely Smith. I like to think that the upper wave represents the atmosphere, which we’re not used to thinking of as a fluid. But it is! Get on a plane and watch clouds sit on the same invisible plane, like flecks of foam on a cappuccino…

<I’m a nerdy but not high-earning/otherwise-impressive guy who’s been reading along and I feel kind of hurt.> Sorry. If I read a blog post on e.g. how people should try dating [my ethnicity] women because they have [appealing-to-men quality] I’d feel a bit bristly about it too. I want to bridge these two complementary but undersupplied dating market segments – and my most effective-seeming pitch to convince the less sold side is somewhat heartless and objectifying. As an apology, let me direct you to the best dating advice for nerdy guys I know of: Jacob Falkovich’s blog post on how he optimized the heck out of his dating strategies.

<You say you’ve been hit on 2~3 times in 7 years of dating. Are you ugly? Is your big life hack ‘dating people with no standards’?> No, I think I’m decent to look at. Photofeeler rates one of my best dating photos at 6.5/10 on attractiveness, which isn’t awesome but makes me solidly ‘okay’. I have a degree from Stanford in an engineering major and earned six figures out of college. (I am an unmistakeable loser on other dimensions – I burned out of tech after several years and am open about long-running moderate depression.) I can afford to be, and am, picky. I admit I don’t filter that much for looks aside from (empirically) height – my male partners average six feet. But I look for funny, kind, intelligent men who are good in bed and will treat me with respect and compassion (and, fine, admiration – I have an ego – but I'm generous with returning it when it's deserved). And I generally get what I want. Which is why I want to tell people who don’t initiate to try it!

<Okay, so maybe you have a great dating life because you have various advantages and you’re insensitively pushing the least relevant strategy to people for whom it won’t work.> Yes. I still worry about this. It was the most compelling reason not to publish this. Blogger with heaps with privilege makes a fool out of herself on the internet. I’ve had some back and forth with trans women acquaintances for whom this strategy is more fraught, for instance. I will say: my partners who say, "wow, no one asks me out” – they're not that picky! They would have been happy for my ping if I'd gone to a community college, been somewhat less physically attractive, or lower earning.

<You’re poly, right? Don’t you think this makes your advice inapplicable to the monogamous people who comprise the bulk of your intended readership?> Can’t rule it out, but I don’t think the dynamics are very different.

<Where are you meeting people?> Tech circles and the LessWrong internet subculture. This isn’t super helpful if you’re not a tech worker or find LessWrong weirdboring, which most people do. I’ve posted a comment saying “straight programmer men, where is the best place a non-technical woman would hang out to naturally meet you?” – they should give you better advice.

<Break it down for me. How do you initiate?>

First I notice a guy. Maybe they gave a small impromptu lecture about the US electric grid at a party. Maybe they write really good blog posts about voting theorems. Maybe I saw their personal bookshelf and saw the same worn book that's close to my heart. After one or more noticing-incidents pile up, I writhe with indecision and yearning, yell with fear into my pillow, and then email them asking them out. Sometimes I put my finger on the mouse button and ask one of my partners to press down for me to click send.

Hey, I think you’re cute and am interested in going on a date with you. Are you free this Saturday afternoon to go on a walk around [place] and maybe come back to my house afterwards to nonsexually cuddle afterwards? Sorry if this is awkward, if you’re not interested I’m happy to proceed with our friendship as if I never asked. :)

<The thought of asking people out makes me anxious.>

They’re probably not going to judge you. If your message was polite and they judge you anyway, they’re kind of a dick and you don’t want to date them.

You’re not going to sound stupid, because you’re going to agonize for 15+ minutes over your 1-paragraph message and remove the obviously stupid things.

If they turn out to be unavailable, just apologize and assure them you won’t be weird about it. (And carry through!)

You’re not going to sound presumptuous – if you’re nervous, assure them you’re okay with a no.

Have a friend available for support online or in your room when you message them. In fact, if you’ve had a ✨THAT PERSON✨ in mind while reading this post, why not message your friend now? “Hey, I’m thinking of asking out ✨THAT PERSON✨. I’m anxious. Are you up for sanity-checking my draft to him and helping me not freak out while I wait for a response?”

Finally: the benefit of the first few reachouts isn’t just that you might get a nice relationship out of it. It’s that you’re developing a mental muscle whose use will improve the quality of your relationships for the rest of your life. I tore out my hair over asking out my first boyfriend, but the seventh time I sent an email to someone I had a crush on, all I did was snarl nyeergh! into my empty room and then dive my finger towards the mouse button. When you’re weighing the pros and cons, consider that practicing might make it so that 3 years from now you’re messaging one interesting person every other month, and going on multiple dates a year with the highest quality potential partners you know.

This is where I am. It is amazing. Join me.