I am interested in your analysis of the older women/younger man trend.  Let’s hear your authoritative point of view.
–Karin

The Harvard MBA says:

A question near and dear to my heart!  I’ve always preferred older women (some would argue that circumstances made this inevitable; I went to college at 15, so going for younger women would probably have been difficult, and certainly illegal) so I’ve often wondered why more men don’t share what seems to be an eminently sensible preference.

There are certainly many biological reasons that men go for younger women–it is incontrovertible that women are at their most fertile before the age of 30–so it is not surprising that most cultures consider young women more attractive than their elders.

Thanks to modern medicine and habits (after all, most now consider 2 children to be the ideal family size, versus the 5 or 6 of yesteryear), these reasons no longer apply, and there is no biological bar to younger men pursuing relationships with older women.

It’s also the case that over the past 10 years or so, there has been a renaissance in the portrayal of the sexual attractiveness of older women.  Numerous examples spring to mind, from the rise of the MILF (first mentioned in mass culture in the movie, “American Pie”) and the parallel emergence of the cougar (here’s an article I wrote detailing my own exploration of the cougar sub-culture), with real-life examples like Demi Moore and Ashton Kutcher.  I don’t have a definite explanation for this, but I suspect that as with most things in American culture, it’s being driven by the aging of the Baby Boomers, who can no longer consider themselves young, but still wish to remain youthful.

Yet while our cultural perceptions may have changed, it is unclear that our habits have done the same.  The dating site OKCupid often uses its data to provide interesting insights into how our actions belie our words (here’s a fascinating article on race and religion in dating that is well worth the read), and has done the same for online dating age preferences.  Here is the key graphic:

As you can see, men of just about any age are willing to message any woman who’s legal.  They even message women who are younger than the age they’ve specified as their minimum.  Here’s the money quote:

No matter what he’s telling himself on his setting page, a 30 year-old man spends as much time messaging 18 and 19 year-olds as he does women his own age.

The irony, of course, is that older women seem like a better match with what men claim to look for in a woman.  Older women are far more likely to say that sex is one of their favorite activites, that they are okay with having casual sex, to be willing to contemplate a threesome, and to enjoy giving oral sex.  They are also more self-confident, and are more likely to say that they are happy with their life. (all stats drawn from OKCupid)

Perhaps older women simply need better marketing.  I’d be willing to bet that if I approached the average single guy and told him that I could point him to a group of women who enjoyed casual sex and were keen on threesomes and blowjobs, and who were also financially independent and less interested in marriage, I’d be dealing with a stampede.

Ultimately, my assessment is that there is a market inefficiency; men undervalue older women and overvalue younger women.  Most market inefficiencies will eventually be arbitraged out of existence; the cultural changes that I pointed out earlier may very well be the leading indicator of just such a change.  But in the interim, I would strongly advise a single guy to take advantage of this opportunity and try to find an older woman.  In a couple of years, she may be out of his league.