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

Three weeks ago, I wrote Bullish Life: I’m Engaged! What I Learned From Twenty Years of Dating, followed by Bullish Life: How I Met My (Soon-to-Be) Husband On OKCupid.

I’ve since turned all my attention to baking and having wedding invitations printed on organic hemp paper folded by Japanese children.

No, not really. Actually, my kick-ass assistant just helped me file all the paperwork for a very specific insurance policy for a business I’m launching on June 1st! And my web designer works on my projects at night when I’m sleeping! I mention this because I wish to assure you that this column has not gone boy-crazy.

I would like to add that I did once have a “boy crazy” phase, but it largely involved Data from Star Trek and ended around 1995. And also, over on The Grindstone (where the dress code allows only two eyeshadow colors: neutral brown and neutral grayish-brown, as opposed to at TheGloss, where everyone is playing Fuck, Marry, Kill all day while making eyeshadow out of scented Magic Markers*), I’ve been writing about why tech skills are not optional for your career, how technology can help overcome discrimination, and how to ask for more money (Q&A on this topic coming soon).

And yet, I had so much material on online dating — thanks to dating pro Judy McGuire — that I thought the topic deserved another post.

I also think that the idea that life advice, business advice, and dating advice are completely separate is a bit silly. Virtually every woman I know regrets having wasted time on some puerile man-child when she could have been getting better grades, improving her career, writing a book, etc. So, the more directly you can achieve your version of romantic contentment, the more time and energy you’ll have for the rest of the components of a gentlewomanly life. Who has the time to go out in real life with some boy who, it turns out, wants/doesn’t want kids when you don’t/do? Or who, it turns out, thinks that the Earth is larger than the Sun? (See last week’s column for my praise of the time- and agony-saving question system on OKCupid.)

So, here are some online dating tips from experts and happy people!

*Completely made up. All the ladies work in the same office, which I’ve only been to once. Everyone wears the same eyeshadow, just like in North Korea.

Emphasize Your Weirdest Features

The OKCupid blog has charts. So, so many charts. They have a lot of data to crunch. Like this: The Mathematics of Beauty.

This post begins with a warning about women being objectified, but then goes on to give some very practical advice: If there’s something weird, conventionally unattractive, or polarizing about you, play it up. Better than some people think you’re ugly and peculiar and others think you’re amazing than for everyone who sees you to collectively shrug. To quantify: What matters in how much attention you get is not your absolute hotness ranking but the standard deviation of the data.

In other words — pardon me for referring to women on a hotness scale of 1 to 10 — a “5” who is ranked “5” by everyone (standard deviation of zero) gets no messages. Who wants to go out with a 5? But a woman who is ranked a zero by half of the male population and a 10 by the other half gets a lot of messages.

So, big sharp noses? Enormous asses? Flat-chestedness? Take a fucking photograph and go with it. All of those things have ardent fans. (The nose thing is mine! I really like prominent, sharp, symmetrical noses. If I were a man, I would propose immediately to Alexa Ray Joel.)

Online Dating Tips From a Pro

And now, some tips from dating columnist and profile-fixer Judy McGuire:

  • Don’t be such an uptight baby. The only people who think there’s a stigma attached to online dating are either smug marrieds (the only good phrase out of Bridget Jones’ Diary) or people who haven’t gotten laid since Bush was in office. And yes, someone you know might see your ad—so what? They only saw it because they’re also trawling OKCupid for tail.
  • Expand your height, weight and age ranges. Casting a wide net makes you look like an accepting, wonderful person. Also know that everyone online lies—men just as often as women—so when you have a cut-off of 35, that’s 45 in online dating years anyway. Decide who you’ll go out with on a case-by-case basis.
  • Cleavage shot. I don’t care if you have an A-cup, squish those bad boys together and show them. Not in a slutty way (unless you want a deluge of penis pics, which is okay too), but in a carefree, “Oops, I left an extra button undone” kind of way.
  • Unless you’re a Friend of Bill (i.e., in Alcoholics Anonymous), skip coffee and meet for a drink instead. Meeting a stranger who turns out to be a foot shorter and ten years older than you were led to believe is a lot easier to swallow over a Manhattan than a mocha grande.

A Few Notes From My Own Experience

  • Anyone whose age ends in “9” is suspect. One man who listed his age as 39 later revealed that he was 43. However, he revealed this via text, before meeting in person, so I didn’t mind too much. Later, he said he believed in lying to machines, but not to people, which led to an interesting discussion.
  • All of the men who listed their height as 5’8″ were shorter. Just FYI. I think the collective male unconscious has decided that 5’8″ is the minimum acceptable manly-male height. Sometimes, you really do have to meet people in person: I’ve discovered that I don’t necessarily mind short guys (especially ones with other masculine qualities, like prominent brow-ridges), but I do mind when guys have smaller hands and feet than me. That’s just creepy.
  • My fiancé and I have noted that we hate a lot of the same things. Nothing brings people together like shared hate! Mentioning things that you dislike (innumeracy, celebrities getting a mere slap on the wrist for drunk driving, incompetence, Ayn Rand, people who say, “Keep the government out of my Medicare!”) can really bring people together, but go light on things you dislike about men. Don’t write an ad specifically to scare away your last three ex-boyfriends. They don’t matter anymore.

Switch Your Profile To Say You Like Women

And go look at what all the other ladies are doing. This is actually really eye-opening, enough to deserve its own subheading.

Starting browsing for a girlfriend, and you may discover that what you think is fresh, original, and witty in your own profile is actually a bit cliché (see below, on the ubiquitous Shot of a Woman Skydiving). I also discovered that, in general, the ladies of OKCupid (at least the ones that came up for me in NYC) were all a pretty nerdy, verbal, witty bunch.

I’m not suggesting that you look at these ladies as “the competition”; it’s just nice to get some context.

For instance: Witty, verbal ladies tend to write long, detailed profiles and then get a bit offended when a man writes them only a one-sentence message, even if it is on-topic and correctly spelled. However, once you realize that most of the ladies on the site are verbose and witty and care about details, it quickly becomes apparent that even the most thoughtful, erudite, well-spoken fellow just couldn’t possibly generate the word count required to send long, smart, detailed messages to woman after woman, knowing that only a small percentage of women are going to write back.

So, don’t disregard one-sentence messages; it’s reasonable that a guy might want to know that you think he’s attractive enough to talk to before he writes a few paragraphs. Lazy second and third messages, though, indicate a guy who’s probably also too lazy to hold himself up on his arms during sex and will just flop around on top of you like a dying tuna.

A Few Amusing Pointers From Men

Several nice and attractive men I’ve polled concur on the following:

  • Stop saying, “I am equally comfortable in an evening gown and in sweats.” Men don’t care what you’re wearing.
  • One man added, “Equivocating in general just makes it look like you’re too eager to please. I like this one thing, and also its complete opposite! There’s no point even writing that.”
  • No more skydiving photos. They look silly and don’t show any of your attractive features. Why are all women showing off their skydiving?!

One man remarked that, while action shots in general were silly and unattractive, one woman had posted a very clever photo of herself getting out of a canoe; she knew it showed that she had a great ass. But, in general, canoes are not a selling point.

Don’t Leave Mankind a Worse Place Than You Found It

And yes, I do mean “man”-kind.

If you had to message dozens of dudes, most of whom didn’t write you back at all, and then ended up on fairly frequent dates with men who, due to a desire to avoid awkwardness and confrontation, pretend they’re more interested than they really are and then just ignore all your followup texts for a second date, you might be driven literally insane.

So, obviously, that’s what men deal with. Some of them aren’t bothered at all (fun numbers game!), but some of them find it soul-destroying.

I’ve been a good citizen (I hope) with frequent use of lines like, “I don’t think we’re a match, but good luck in your search!”

In extreme situations — a smart, clever guy who I am just not attracted to in the least is really trying to persuade me to go out with him — I’ve even dropped, “Hey, you are obviously a high-quality guy, but I’m really at the point in life where I’m looking for THE ONE, and I don’t think you’re him, even though you sound really cool. Good luck in your search!”

I’ve never once had a guy reply, “No, I’m totally him!” (Ha!)

In fact, most men are taken aback (intimidated, impressed?) by a woman who doesn’t think “I’m cool, you’re cool” is a good enough reason to hang out. For that matter, most men are taken aback by a woman who doesn’t “hang out.” (See Bullish Life: Achieve Goals and Glory By Recreating Like a Total F*cking Badass.)

Gentlewomanly Dating

Technology, when well-designed by human beings, can be an excellent force in crafting a gentlewomanly life.

Online dating can keep creeps and idiots compartmentalized; you can shut your laptop on them and they go away!

And online dating can allow you to get direct answers to important questions (“How long should you date someone before getting engaged?”, for instance) before being swayed by alcohol, devilish grins, and witty jokes. (I’m sorry, but Brooklyn is full of men who had no luck with girls in high school and have since realized that literary references can get them laid, and their newfound power has turned them into assholes. I call this type “The McSweeney’s Player.”)

I’ve met very few women who are able to completely put aside romance and sex for years at a stretch while working on their goals, even as such women sometimes recommend this course of action for others. So, I think it’s actually pretty important in a conversation about productivity, achievement, and career design to talk about how to run our romantic lives well, so that we move towards what we want without derailing the other things we want in life.

Send in your questions to bullish@thegloss.com or follow on Twitter @jendziura. See a Bullish archive here.