Yes, it's hard to date as an ambitious woman

But not impossible.

Another week, another panic about how no one’s dating anymore. This week, we have this WSJ article titled “AMERICAN WOMAN ARE GIVING UP ON MARRIAGE!!!!”

This article is paywalled (my link is a gift link, from some kind soul which you can read in its entirety, though). So no one read the article and force-fit their own pet theories on whether it was true, and why it might be so. The shared image was this, which only added fuel to the fire.

Half the people are wishing for Katie Kirsch to end up as an old cat lady who gets eaten by cats, and the other half are saying, “No, she is a grifter with an awful personality; it has nothing to do with ambition”. But IN THE ARTICLE ITSELF, it is revealed that she now has a boyfriend.

Yet Katie’s luck may be changing. She recently started dating a man she was set up with who seems both interested in starting a family and supportive of her career. She admitted she was wary at first: “I thought it was too good to be true.”

Cartoons Hate Her wrote about this, as we all awaited. Her stance on this has been that men are not turned off by women making more money than they do, and if anything, prefer working women to SAHMs. She backs this up with her own surveys on the topic. Which is A LOT better than articles written on this out of thin air.

I don’t dispute the data. But my own experience renders this data incomplete, and I thought I’d dive deeper into this.

My friends and I are all ambitious women

I went to a top-ranked university with a highly competitive entrance exam. The men:women ratio was 7:1. So not a lot of women, but most of us were neurotic and nerdy. When we get together, it feels like we’re better equipped to raise a few billion in VC money than organize a kid’s birthday party.

It’s been a good 15 years since we graduated, and some of us now have children who are preparing for the same entrance exams, so it’s good to take stock now.

Most of us were married by 30. A few are still single. I married later than most.

The difficulties of dating as an ambitious woman

My closest friends were paired off by 25. It took me a while longer.

The ones who found a partner quickly tended to have done so in college or grad school. Which was a smart move, because when you’re in college, your ambition just looks like getting top grades and winning hard in other structured settings. Not emasculating a man.

I struggled with mental health and was confused about my sexuality in college, so I avoided dating then. But even there, it was clear what kind of women were in demand.

There was a preference for fun, feminine women. Nothing wrong with that. But the men in question weren’t fun, masculine men. They continued to be obsessed with nerdy, niche tech stuff, focused on competitive programming, and made cringey nerd jokes.

If you inhabited that space as a woman, though, they didn’t see you as a potential partner. Potential partners were supposed to be the ones who took a load off your shoulders and helped you relax. Not making you listen while they went on and on about the preparation techniques of Chinese competitive programmers. Or, even politics. Men, however, did all of this.

The conflict here is simple - Men can let their work and interests define them — it’s seen as impressive. Women are expected to knock it off to be dateable, because we doing it is a turn-off. Ambitious women get penalized for the very drive that makes men desirable.

Ambition and the real world

Still, in college, this was fine. There were always opportunities where you’d nerd out, and opportunities where you’d knock it off. You’re living with a thousand other men and women, and you get to know each other as whole people, and fall in love when fate wills it.

The real world is more challenging.

I’m a nerdy person. Show me a normal activity, and I’ll champion-nerdout on that. And, four years with the best nerdy dudes meant the things I was most interested in were male-coded, like tech, urban design, politics, and foreign policy. I was interested in female-coded things too, like comedy, astrology, and celebrity gossip. But… I was quite serious about those as well. Like I’m not a ‘Omg you’re a Taurus’ kind of astrology girl, I’m a “you have a star on your Mount Of Saturn, that means assassination” kind of astrology girl.

This is, predictably, not the best kind of woman to be while dating.

By the time I was seriously dating, a lot of my female friends were already in relationships that were heading to marriage. When I finally paid attention to my male friends, it seemed like they had a different thing going on.

They’d be dating women several years younger. They’d talk about how ambitious those women were. But the vibe was just very different from how my female friends were dating. My female friends were dating men who were their peers, like a classmate or a fellow intern. My male friends were dating women who looked up to them. Like, a student in a class they TA’d for, or an intern who reported to them.

My colleagues at work were from all over the world with different paths, but everyone was kinda top of their game. The women were dating or married to men who were a peer in some way, like maybe in med school or a structural engineer. The men were dating or married to actresses and dancers. I somehow never came across a techbro who was married to another nerd - it was, AT BEST, someone in HR or someone who was a peer but several years younger. More typically, their wives or girlfriends were in some incredibly pink-collared profession.

I did try dating like that — I was active in the creative scene and tried dating men from there who were aspiring actors and such. But… I didn’t like how annoying they were to talk to. They could look really good and have great social skills, but it felt like my mind was atrophying talking to them. The only one I ended up vibing well with turned out to have dropped out of an advanced math degree.

So it became clear to me — women who were in cognitively demanding fields valued high cognition, but the men didn’t. Everyone said their wife was “so ambitious,” but the ambition was always something that didn’t interfere with or undercut their own, and, most importantly, it seemed like their wife did all the household chores.

I dated men in my range of ambition, mostly in STEM careers. Several expected that my career would be expendable while theirs wasn’t — even when I was earning twice what they were. They fully expected I’d take the lead on any and all childcare. It seemed like elder care would fall to me as well.

A good number, however, were fine with wherever life took us.

But a bigger issue was that the personality that made me good at tech and writing was not welcome in the dating scene. I am talkative. I’m told I’m bossy (I don’t agree). And I liked arguing about obscure stuff. Outside of dating situations, I received no pushback on this; if anything, it led to a lot of fun conversations and great friends. While dating, it was a distinct liability.

Now, there are two aspects to this - first, the chatty, argumentative persona rubbed men the wrong way on the first few dates. And second, the long-term ambitions and prioritizing my career resulted in things not going long-term.

Friends told me I needed to laugh at men’s jokes instead of dissecting them, and make myself seem more ditzy than I was. I tried it, and ended up in a relationship for a few months. But the whole time, I felt like I’d blow my brains out three years into marriage. I wasn’t myself in that relationship. Sure, he was highly supportive of my career and shared my scintillating interests, but it felt like he always had to have the upper hand, and there was no room for my enthusiasm. I broke it off. He’s now married to a highly successful woman who is happy letting him be the smartest person in a room.

I wondered if I could marry someone who prioritized their career less. I found a few men like that who were still fun to talk to. The problem, however, was they didn’t make up for that by being extra good at managing the home and family. It felt like I’d have to do everything anyway, while also dealing with their resentment, and on a lower budget.

Many things make my husband the perfect one for me, but he proudly told his friends, “She makes more than me!” and that note of pride in his voice was all I needed. Plus, we’d watch standup, and then spend an hour over dinner dissecting the jokes. And, he prefers to go deep into topics we’re interested in rather than argue. Over time, our incomes leveled out, and I was a stay-at-home mom for a while. But that respect for my career and interests had been missing from everyone else.

IC Husband, Manager Wife - How Things Panned Out

Somehow, I see the Narayan Murthy - Sudha Murthy pattern play out a lot among both my male and female friends in tech - wife is a rising star at a stable, large company, and is usually on the management track. The husband is one of 1) a Deep tech individual contributor, 2) a Maverick entrepreneur, 3) a secret third kind of rule-breaking trailblazer with enough time to do more childcare. Sometimes, all three.

The older husband/younger non-peer ambitious wife and the matched-peer wife/husband doesn’t make that much of a difference long-term. The ambition gets tempered by ability.

If either is in academia, the wife’s thesis acknowledgements include the husband helping her code up her hypothesis and double-checking her math, while the husband’s include an acknowledgement of the wife proofreading his thesis and providing unflinching faith and support.

The colleagues who married the actresses and dancers are now comfortably in middle management, while their wives are stay-at-home moms or work in sales or as executive assistants. They seem to take more of the childcare responsibilities.

Which means… not that much room for the female deep tech ICs, maverick entrepreneurs, and rule-breaking trailblazers.

The ones I know tend to be single, or have had a contentious divorce.

What does a maverick trailblazer need?

We all know of someone who took a high-risk, high-reward path, and was supported by their spouse the whole time.

One of them, of course, is Narayan Murthy. He’s a classic case study. Let’s go into his life.

So his wife, Sudha is the bubbly, noisy sort from a supportive well-off family. He’s a nerdy squint-eyed dude with what seems like a dramatic, stressful family background. But what he did have was raw intellect, and strong principles. They were both equally qualified to run Infosys. Heck, she helped him write code initially, and also gave him his seed money from her savings. And, she had been the first woman to study at her engineering college, and the first woman to work on the Tata shop floor, so she was no shrinking violet.

He said, only one of us can work at Infosys. If you want to do it, I’ll step away. She considered it hard, and something her grandmother said to her came back to her - a woman can do anything a man can, but a man can’t do some things that a woman can. She decided to let him be the trailblazer, and she took on a supporting role. First, she worked a steady job so they might have an income when he was struggling. Then, she decided to prioritize their children and worked as a computer science teacher in a girls’ college.

He became a multibillionaire. She became a public figure and is now a Rajya Sabha MP. And, their daughter was the First Lady of the UK, the first one of Indian origin. So… that worked out well, I guess.

I haven’t gone too deep into the Obamas, but they also fit this archetype. She was his boss while he was an intern. And then she supported him as he became a community organizer and got into Chicago politics. Eventually, he became President. Same with Usha and JD Vance - she comes from stability and success, he doesn’t, and she pushed him into success.

Maybe it takes a bit of crazy to be ambitious, and the job of a partner is to provide stability to contain the crazy. Look at Elon Musk — no stable partner to contain the crazy, and he just accuses random people of heinous crimes (that likely his father is guilty of ) on Twitter. It could be argued he’s too crazy for a stable partner. From his first wife’s Quora posts, it seems like he had no respect for her.

Let’s look at a trailblazing woman - Tina Fey. In her memoir, she says star male comedians are rulebreaking crazies, but star female comedians are good daughters who ticked all the boxes. She doesn’t seem crazy though, just a workaholic. She says her husband does all the driving and all the cooking, and he is deep enough in her field to create with her. So she gets that direct support from him, and he’s happy to take over the support role when she’s showrunning on a punishing schedule.

Spiky Genius Women

The wife/mother/matriarch role doesn’t lend itself to being really good at one thing. You’re constantly scanning the environment to anticipate others’ needs, and using a variety of skills at a low level. No one cares if you’re realllllly good at cleaning a house, but they care if you’re not that great at cooking. Feminine roles expect you to be a little good at all the things.

And it absolutely doesn’t lend itself to deep work. If you’re responsible for children, you cannot focus for long periods on one thing. You’re constantly interrupted. It’s hard to say NO to the asks, because they feel like your job. And often, those asks (e.g. a child asking for a hug) give you more validation than any kind of deep work. Like, you aren’t even doing anything active most of the time, you’re just like hanging out doing something shallow, so a child can interrupt you when they need you.

It’s hard to be a spiky genius woman like this.

For a lot of women, it isn’t even children that kick this off - we’re often trained to anticipate the needs of those around us anyway, or people around us expect us to. If your focus is taken by organizing the office birthday parties and outings, it’s hard to get used to spending days on bugs by yourself.

If they are expected to constantly anticipate their partner’s needs and live life by their schedule, then, yeah, women aren’t going to get to be spiky geniuses and maverick entrepreneurs. If you need to get rid of your single-mindedness to find a partner, then, yeah, you’re not going to get to be a spiky genius.

And, most importantly, math and science are important for spiky genius work. If girls lose confidence in their math ability in middle school in the US, then, yeah, there are going to be fewer female spiky geniuses. Just persisting with math problems even when you don’t see a solution is how you get good at it. If that is not encouraged, or actively discouraged, there’s going to be fewer female spiky geniuses.

Putting it all together

• Seems like the data from CHH’s survey captures the median college-educated working couple. Neither are geniuses. The woman is likely in a field less given to spiky geniuses than the man. The man likely makes more money, but can’t imagine being the sole breadwinner, because they probably need both incomes to make the mortgage and daycare while still saving money.

• The real status symbol isn’t finding a woman who wants to be a housewife and marrying her. It seems to be to find an ambitious woman and then convince her to be a housewife. I don’t particularly see a problem with this. Kids need to be around ambitious, well-educated moms. Besides, most moms want to spend more time with their kids, and would prefer part-time work or longer parental leave. If Dad can make that happen, everyone would be happy.

• This old family friend of mine, who is an elderly businessman with only a highschool education, once told me, “An engineering degree makes a girl a saleable commodity in the marriage market”. His daughters weren’t highly educated, but he spared no expense in ensuring his granddaughters were. A college degree is a signal that you have middle-class or higher sensibilities. It’s so easy to get one; if you don’t have one, it indicates something is wrong with you. So filtering by college degree doesn’t mean that much today. Maybe we should filter by professional degree instead?

• Dating is going to be hard for you if you’re a spiky genius/maverick entrepreneur/secret third thing woman. Getting dates isn’t the problem. Figuring out a vision of life that a man wants to share with you is. You’ll have to think out of the box on your ideal partner, and be willing to take a few risks.

• Knowing many genius-type men and women, it feels like more people than we realize are one supportive partner away from doing something mildly world-changing. So, support your partner’s crazy!

So, maybe Katie Kirsch wasn’t wrong to be wary. Maybe finding a partner who sees your ambition and doesn’t flinch is too good to be true at the outer ends of maverick. Or maybe, just maybe, she found her supportive crazy-containment unit. Here’s hoping!