AAAH Round #5a: Obvious Failure

The internet is littered with dating advice for men – blogs, forums, ebooks, Youtube channels – but single women are a relatively underserved market. Why is this?

One possibility is that women are naturally better equipped than men to navigate the rocky currents of the 21st-century meat market. Another is that mainstream sources of women’s dating advice – magazines, pop culture and such – already provide women with all the useful advice they need. Or maybe women’s romantic outcomes are simply independent of the actions they take, and working to improve them would be as futile as studying for an IQ test.

Predictably, I am skeptical of those answers. So the question remains: Why are women so much less likely than men to doubt the conventional wisdom on sex, dating and relationships? Simply, it’s because Sexual and romantic failure is much more obvious for young men.

Let’s consider two young, urban professionals in 21st-century America – Michael, and Michelle. Both are 28, healthy, decent-looking, and reasonably successful in their careers.

Michael hasn’t gotten laid in over a year. The thought of finding a girlfriend consumes him. Every solitary night is a fresh reminder of his failure to satisfy his primal yearning for sex and companionship. He dreams constantly of his ex-girlfriend, who seemed quite mediocre at the time they dated, but has since flowered into a titanic paragon of beauty and femininity in his mind’s eye. She was the 3rd woman Michael had slept with in his life, and she left him after a 4-year relationship because she “just wasn’t feeling it”. He was about 90% sure she had been cheating on him.

Every Friday, Michael goes out with his friends to a bar. Mostly, they just sit at their own table, pretending not to envy the men around them flirting with all the available women. Towards the end of each beer-fueled night, Michael will occasionally find the courage to clumsily approach a girl one could charitably describe as “attainable.” She invariably shoots him down, after the three minutes it takes Michael to say hello and buy her a drink.

Michael pays for an account at an online dating site, and he sends out thirty or so messages, several times per week

From these 100+ weekly messages, he eventually nails down one or two 100$ dinner dates. The only women who accept his offer for a second expensive dinner are the ones whose online pictures grossly exaggerated their attractiveness via creatively-angled and outdated shots.

Michael works 60 hour weeks as a sales rep for a mid-sized property management firm. After six months spent falling deeply in love with the new receptionist, Michael finally found the right moment to ask her out. She politely declined.

Tormented by his consistent failure, Michael has started demonstrating signs of clinical depression. He recently learned that a beer or six every evening makes it much easier to fall asleep at a decent hour. Still, he seems to always feel tired. Because of all the drinks and dinners he buys, not to mention the decent car, nice apartment and clothes that he feels are prerequisites to dating success, Michael has lived paycheck-to-paycheck his entire adult life.


Michelle, on the other hand, feels great!

Her job as an HR administrator for her state government can get boring, but the money and benefits are great and she’s out by four almost every day.

She loves her friends, and they hang out all the time – going out for coffee, drinks, shopping, the beach, concerts. They’re in their late twenties, and they still don’t know what they all want to be when they grow up. LOL!

Michelle has a boyfriend. Well, sort of. She’s learned that guys really, really don’t like to have “The Talk.” But the new guy she’s dating has been coming over 2-3 nights a week for a couple of months now – usually just for sex, but sometimes if it’s a weeknight they’ll watch a movie, and once he even took her out to his friend’s art show on a Saturday afternoon.

Michelle met her boyfriend when she was out with the girls to celebrate one of their birthdays (Jessica’s, maybe?) He was super-hot, and since she was still celebrating her breakup with a previous boyfriend, she felt no qualms about sleeping with him the night they met.

The boyfriend before was…

Well, he was really sweet. He and Michelle had dated for about six months, and at first, he seemed cute and smart and funny. But then he started to get all needy! Like, he always wanted to talk and hang out, and he got her a really nice bracelet and a weekend trip for her birthday. After only five months! I mean, it was nice. But ugh.

Once they broke up, Michelle went on a bit of a tear, sleeping with eight different guys in only a month and a half. It was fun, but she’s been content to settle down for the past little while.

Even though she has a boyfriend, Michelle still loves her weekly girl’s nights out. It’s a nice reminder that – even though she’s twenty-eight, has put on a few pounds since her undergraduate days, and perhaps has the hint of crow’s feet and a double chin besmirching her once-cute face – she’s still got it! Sure, she doesn’t turn as many heads on the beach as she did half a decade ago, but she still gets at least as much attention in the bar, owing to her vastly improved flirting skills.

Does Michelle want to have a family some day?

Well sure, she would respond – I guess. But that’s something she’ll do when it’s time. Also, it’s supposed to just happen. In the meantime, she is 100% happy to continue living her awesome life – great job, great friends, a hot boyfriend, and a constant stream of male attention re-affirming her desirability and wealth of options in the sexual marketplace.


Michael and Michelle are both very common archtypes in the cast of characters acting out the tragedy that is Generation Zero. The second half of this post will be published later this week, to give our live studio audience a chance to weigh in. For now though, ladies and gentlemen of the Commentariat, I put it to you:

Which of Michael and Michelle has a brighter future?

Edit: As Elliot points out, the question is a softball. Feel free to ignore it, and riff on anything you like.