Bullish Life: I’m Engaged! What I Learned From Twenty Years of Dating

Oh look, I got engaged!

I’m happy and all, but if you talk about that too much, half the women you know are all like, “Bitch.”

So, let’s talk about the fact that it is now normal in our society to date for twenty years or more before marrying (or the equivalent).

It is also, of course, normal to never want to get married, but that strikes me as a different thing. Spending twenty years doing something you plan to do forever is not the same as spending twenty years gearing up for the thing you really wanted to do in the first place.

A brief history of awkward man-encounters

I think my first “date” (it’s hard to say what is and isn’t a date in 9th grade) might have been in 1992, when I told my mom that a lot of orchestra kids (the coolest!) were going to go to Chuck E. Cheese and play all the games ironically. My mom nodded. Yep, that sounded like something we would do.


So, she dropped me off at the Chuck E. Cheese, where I waited for about ten minutes, heart pounding. And then — get this! — I walked across the parking lot to T.G.I. Friday’s, where I had milkshakes with an older boy from community orchestra. (Sorry, Mom! I’m sure you’re so disappointed in me!)

Afterwards, I walked back to Chuck E. Cheese, where my mom picked me up.

So, obviously, that was awesome. It was also twenty years ago (I’m 33).

After the Chuck E. Cheese guy, there were some real boyfriends in high school, once I was technically allowed to date, and then there were boys in college (back when the liberal-arts bubble of college plus a few women’s studies classes and Pride events convinced me that my generation had done away with useless gender roles for good — haha, not so much).

Then comes the era of Men Whom You Live With: there you are, hopefully integrating book collections and tossing your collective extra copy of Outliers or the Harry Potter series or Infinite Jest. Or maybe tucking your nostalgia-imbued childhood edition of The Hitchhiker’s Guide to the Galaxy on a back shelf just in case…. And then the breakup comes and someone’s putting books in boxes and they always take your Camille Paglia and leave behind their Learn Japanese in 30 Days, and you keep looking at it quizzically, like, “Well, maybe I really will want to learn Japanese.”

You can lose so much fucking time over this stuff.

(See Bullish: Picking a Boyfriend Who Doesn’t Hold Back Your Career or Bank Account.)

And then there comes the point when you start encountering men who are really, seriously looking for a life partner, so much so that they come off all weird. If you’ve been raised, somehow, to think that all men are after sex all the time, it can really throw you off when some guy asks you on a first date whether you have a family history of mental illness, alcoholism, or cystic fibrosis.

And then, maybe — in certain social circles — there comes the point when most people are looking for a life partner, and then things suddenly get a lot easier. Well, not easier, but easier to understand. For instance, I had the following text-message exchange with a 42-year old man I went on five or six dates with last year:

Him: “I think I need to cancel our date. I like you, but I don’t want to get into a serious relationship unless it feels right.”
Me: “OK. Thanks for telling me now rather than later.”
Him: “Thanks for not calling me an asshole.”
Me: “Nope! An asshole would drag it out until he found someone else to have sex with.”


In New York, this stage — where most people are looking for a life partner — comes at least a decade after it does in most of the rest of the country, and in many subcultures (see this Bullish from the woman who was having trouble making a living as a circus photographer), it never comes at all.

In any case, I think there are some advantages to the brave new world we live in, in which you simply don’t expect to spend the big bell in your bell curve of life married to one person. Or at least, some ways you can choose to view the situation as having certain advantages.

In praise of a decade-plus on your own

I care about getting credit — and professional respect, where it’s due — for my work. I care a lot. I don’t see any point in the false humility of pretending otherwise. Professional respect is an important part of a gentlewomanly life. (See Bullish: How To Run Your Career Like A Gentlewoman.)

I realize I’m an extreme case, though. Once, a boyfriend whose mother had a PhD corrected my pronunciation of a word and I was angry for days. I earned my knowledge of how big words are pronounced! His was all cultural capital, transmitted to him in the womb! (The word was “disconsolate,” which is not pronounced “dis-con-SOL-it” but rather “dis-CON-sul-it,” which makes it sound like a verb for depriving a nation of its embassy.)

If you are a married woman who has nice things, people will often assume that someone other than you paid for them. If you are a married woman who starts a business, people will often assume that you had a cushy launch, with a husband paying the bills, or that your business is just a cute little way to make some “extra money,” rather than something intended to provide a real living or expand into a large enterprise.

If you start a business with your husband, people will make even more assumptions — at the extreme end, that it was all his idea and he just put your name on the paperwork so he could take advantage of all those “amazing” opportunities for women-owned businesses. (Side note: Set-asides for women-owned businesses are only helpful if you can provide 250,000 wingnuts per month to the city of New York, or supply janitorial services to an entire military base. I did once meet three guys who ran a truck-rental business, put their wives’ names all over the paperwork, and used women-owned business set-asides to get contracts. I hoped their wives divorced them and took the company.)


There are some benefits to establishing your career as a single woman. The need to make money in order to purchase food is a big one. I suppose this is an “advantage” in the same category as not having rich parents. (See Bullish: Social Class in the Office).

If I had had a partner in life — and even someone you live with can be far from a partner in life — I don’t know that I’d have felt the same sense of urgency to make a suitable number of figures, to publish books, etc. I know that, in some blue-blooded families, the conventional wisdom is not to marry until you’ve gotten your masters. For me: Don’t couple up until you’ve finally got a damn Wikipedia page?

I feel like if I had let someone step in and help before I had figured out how to run my own ship, I would never have learned to run my own ship. The system would have too many variables for me to be sure of my own fortitude. And if couldn’t manage a career and some personal finance, how could I run a real company?

I do a lot of things for a living (and constantly talk about multiple income streams), one of which is working for a company at which I get paid on a per-class basis to teach classes. I was talking to a coworker who chooses to work a fraction as much as I do; then he uses the money to go live in a hut on a beach somewhere for months. I’m not against that kind of plan, but when he asked, “Why do you work so much?”, it seemed a little intense to reply, “So I can have a baby on my own if I don’t meet the right man.” So I said, “I want to buy an apartment before I’m 35.” (I don’t know where that came from, and for the record, I don’t think real estate is necessarily as good an investment as people think it is. I prefer to diversify my investments, and — since I am full of youthful mojo — mostly invest in my own businesses, and not be responsible for things like replacing a faulty boiler.)

I have often written that, if you want to have children, you have precious little launching time between when you graduate from college and when your eggs die — maybe 12-13 years during which you need to go from being financially dependent, to financially independent, to financially responsible for others. When the stakes are so high, I don’t know why we can’t talk about this more openly. How many lady-friends do you have who tell you everything about their sex lives, but you have no idea what they make at their jobs, whether they’re getting money from mom and dad, and what their financial goals are? (See Bullish: How Talking About Money Can Make You More Of It.)

Laura Vanderkam, whom I have quoted often, remarked (see The Princess Problem) that one of the reasons women make less is that they ask for less, and maybe one of the reasons young women ask for less is that their idea of “enough” money is based on taking care of themselves, whereas young men’s idea of “enough” money often assumes the need to eventually take care of others. We need to raise girls to assume that, at some point in their lives, they will be breadwinners. Maybe for a brief period while a partner is unemployed, and maybe for a lifetime. Maybe on and off, over the course of a lifetme.

That said, I just met up with a friend from out of town who got married last fall. She said something lovely and hilarious:

“I’ve never had more mental space as I do now that I’m married! When you’re not worried about dating, it frees up this whole brain region for other things! Who am I going to have dinner with? My husband! Who am I going to have sex with? My husband! I’ve never had more time to think about my career!”

If I could do anything differently…

A reader wrote to me a few months back and said, amidst some other comments about extreme advance planning, “I have your quotes printed and pasted on my walls! ‘Be Ballsy,’ ‘Pitch Things’ and a really long quote about boys and finding one once you’ve established a career.” I was very flattered and asked for a picture, if she didn’t mind. And she sent it just yesterday!

I stand by this advice! I can’t even find the column it came from. I’ve written a lot of columns.

I was also pleased to be on a wall with Rocky. (See Bullish Life: What I Learned From Being Captain of My College Debate and Boxing Teams.)

So, if I could do anything differently over the last twenty years, I wouldn’t have skipped so many college classes to spend time with some dude. I wouldn’t have blown deadlines for dudes. I wouldn’t have thought I could compete with a guy’s band. I wouldn’t have assumed that men magically get more mature as they age. Also: you might as well make a plan and get to work, because the guys you attract when you’re down and out are mostly not good guys. Some are, of course. But plenty of men make a virtual career out of finding women at a low point in their lives; their “solution” to your problems is pretty much to pat you on the head and offer their dick-based ministrations.


Also, I think a lot of people enjoy the emotion of being indignant, much to their own detriment. So, they date men who are basically bound to disappoint, so they can be rightfully outraged when those men violate various rules that may or may not exist. There are basically just no universal rules anymore.

As I wrote in Bullish Life: 3 Romantic Mistakes That Young Women Make That Cause Weeping Among The Angels And Kittens, we live in a culture and era with no script. Assume nothing. For instance, do not assume that a relationship is leading to marriage, or that because someone says they want to have kids and keeps dating you that they want to have kids with you, while you are able to do so. Assume you are dating a wolf-person raised by wolves. Or else that you are the wolf-person.

Also, don’t take romantic advice from anyone just because they’re married. Plenty of people are total fuckups who just happened to meet a really similar fuckup.

The rules that function when rules don’t exist

While I do feel that I’ve wasted a fair amount of time, it also seems undeniable that, even for those who want to get married, every relationship we have in the interim isn’t just a failed attempt at marriage. Surely, there is some value to romantic companionship throughout your turbulent younger years. Even having a fairly lame boyfriend at the ready kind of quiets down the part of you that otherwise, due to various evolutionary drives, cannot allow you to get your damn work done without running your mate-radar and advertising your best features.

Obviously, you can learn things from various people who aren’t right for you long-term, although I think that there are really two camps here: People who feel you can spend a couple of years with someone, learn a few things, change a little, break up and move on, and people who think you can do all those things, but at some cost to yourself — that coupling and uncoupling so many times causes you to sustain some collateral damage.

If our brave new world requires us to couple and uncouple repeatedly, with little expectation of permanence, what are the rules for doing so with decency? Can there be any such thing?

I do think that we, as a culture, could develop a set of largely gender-neutral rules that involve being upfront, communicating in a painfully literal manner, considering the best interests of whoever you’re fucking, and not wasting each other’s time.

As such, I think my best move ever was pretty much the OKCupid ad designed to repel all the men I find repellent! It contained the sentence, “Please be secure with the fact that your youth is over.” And also, “I enjoy punishing wrongdoers.” (I do!)

It was a start.

(For those of you who want details: We met in November on OKCupid. He’s 40 but looks 30, works in IT, and knows a lot more than I do about The Lord of the Rings. He makes a lot of puns. My favorite may be: “Don’t count your Chechens before they’ve taken Grozny.” I don’t care much about weddings and will now return you to your regularly scheduled Bullish programming.)

originally published on The Gloss

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