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

Jennifer Dziura writes life coaching advice weekly here on TheGloss, and career coaching advice Fridays on TheGrindstone.

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.)

Send in your questions to bullish@thegloss.com. See a Bullish archive here.

Share This Post:
    • Megan


    • LCT

      This was fantastic. And as one of the freak shows out there who married the second person they dated, let me say this was so enlightening and informative. I can’t know what being on the other side of the commitment coin would be like, but this gave me a glimpse.

      I’m totally behind you 100% on the gender-neutral rules. Let’s get it started.

      And congrats! Don’t let the wedding-planner Man getcha down.

    • Liz


      As someone who just moved in with a man I met on OKC through an ad designed to repel the repellent, cheers!

    • Niamh

      Congratulations! Your columns are my personal career coach, and I hope your fiancé is the badass gentleman you deserve. Wishing the two of you a glorious, long, and very happy life together.

    • Eve

      :) So happy for you. By the way, I think I forgot to tell you this and you’ve probably figured it out already anyway, but if you can find a one-stop shop place, do. Right before I got married, everybody kept telling us that we must be so stressed planning a wedding. Nope, we just gave the lady money and showed up on the right day. It was awesome. Didn’t have to worry about catering, flowers, anything. I even bought my dress there.

    • Lindsey


    • JaneM

      Looking at pictures of you Jamie and Jen W I wonder whether looking like a cross between Audrey Hepburn and a ballerina is a requirement to work at the gloss.

      Your man and upcoming marriage sound great, too.

      And your column is so good that I can’t even hate you.

      Fuck you, and mazel tov!

    • Bob V

      >OKCupid ad designed to repel all the men I find repellent

      Will you post this someday? I’d love to read more breakdown of what you wrote and why.

      • Jennifer Dziura

        NEXT WEEK! You read my mind.

        Also, ALL THE SINGLE LADIES: Have you done this? Set up a personal ad designed to repel, rather than attract, the majority of prospects? Email me with anecdotes, please. Bullish@thegloss.com


      • Carla

        Nice! I was just about to ask for that too. My first reaction was that I definitely needed to revamp my profile.

      • mellow_yellow

        I am looking forward to this article, patiently waiting…

    • EKS

      Congratulations!! (And great article, per usual.)

    • kid


    • Jennifer Dziura

      Thanks so much, everyone!

      Also, JaneM: Ha! No one has ever said I looked like Audrey before. I usually get Shannen Doherty.


    • Cary


      Check out a practical wedding and off beat bride for some kick ass, feminist and nerdy advice on wedding planning.

    • Sabrina

      Hi Jennifer!

      First, congrats on the engagement :)

      Second…I just started reading your column, and I LOVE it!! I’m about to copy the girl you quoted, who posted your quotes up – you have some really great words to live by.

      I’m single…been single for around 8 years. I have to say, it’s frustrating! I have an OKC account as well as pof, although I’ve basically given up on both of them. I have written very specific things that I want and don’t want, and I don’t think guys read my words at all!!! Or if they do, they try to find SOMETHING that will make them work for me. And for some reason, I get zero emails on OKC, so I’m a teensy jealous that you actually met a great guy on there! :)

    • SG

      I read this while I was blowdrying my 23-year-old hair to prepare for the “corporate world”… but now feel empowered to not even look at a man until I’m making six-figures. That will certainly save me time in the mornings!

      Fantastic article – thoughtful and thought-provoking.

    • Emily

      Congratulations and best wishes.

      Even if you don’t care about weddings, check out A Practical Wedding (book and blog). I am not affiliated in any way, but I am one of thousands of modern, practical gentlewomen who nearly called off her wedding after 15 minutes with Brides magazine but were calmed by Meg’s no-nonsense take.

    • HaydenT

      First of all, CONGRATU-FUCKING-LATIONS! He must spectacular because I know your standards are high…(which should be ‘normal’ but I digress.)

      Second of all, the truth is that you date at your self-esteem.

      When I met my husband, I had just turned 22 years old and graduated from college. I was also ‘the shit’. Not to mention that I had grown up with an abusive father and was determined to never.ever.never let that happen to me. I was, therefore, 5,000% cool with being by myself. (As far as I am concerned, I am GREAT company, so if I am by myself, then I am never alone.)

      When I added Chris to my rotation of guys I would ‘let’ take me out, marriage was not even on my radar. Not for YEARS. He loved it; every minute of it. He loved my self-assurance and how I knew exactly what I wanted from a relationship and life.

      He went from a guy known for being anti-marriage (his birthday cake from an ex was topped with a groom-running-away-from-a-bride topper) to being “FUCK YEAH, MARRIAGE!”

      Now, if only I could translate that balls-to-the-wall badassery to my career.

    • Christina

      Congratulations!! Wedding in NYC? Wedding in VA Beach? Pictures…??

    • Stephanie Chen

      This is extremely belated (I’ll admit I’m behind on catching my Bullish fix) but:


      b) Excellent post. I particularly liked the part of this post where you talk about married women who start businesses/women who start businesses with their husbands and the assumptions that are often attached to those situations. Definitely needed to be pointed out.

      You are one of my favorite writers and an inspiration, Jen!

    • Slightly Embarrassed for you

      Is that really your name? Dziura means “hole” in Polish.

      • Alicia


    • LynnKell

      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.


      I would say “take romantic advise from a person who is or has been in a situation you look up to”

      I think I read in another article that you are now married, so, Congratulations!