While I'm uncharacteristically writing about the dangers of dating younger girls, I might as well get this out of my system too. Even as a senior in high school, I was pulled toward the freshman and sophomore girls, and my love of younger girls has not diminished since then. However, there have been a few special females who, despite being older, have managed to intrigue me. If they won over someone who has such picky tastes regarding age, they could win over anyone. Aging women, take notice of these traits.
To sum up the series in advance, the three common factors underlying the appeal of these older women are, in order of decreasing importance, 1) looking much younger than they are; 2) maintaining a girly personality, in this sense; and 3) having an aura of reserve and mystery about them. The trend toward a more reserved and mysterious demeanor parallels the steady decline in Extraversion as people age, so these women did not try to reverse their changing personalities but to make the best of them. Becoming witty and urbane had nothing to do with their charm.
As an aside, this explains why cougars fail to interest anyone other than the woefully desperate: they may or may not look fuckable, but they have a manly personality, appearing strong rather than vulnerable, and being too aggressive. Moreover, as exhibitionists, they leave nothing to the imagination -- and at their age, it's really wiser to cover up.
Steven Pinker wrote a book whose thesis was that much of modern life, especially some of the more undesirable aspects of it, could be traced in part to a belief in The Blank Slate. Certainly, the cougar phenomenon supports his thesis, as these women foolishly cling to the ideology of the perfectability of (wo)mankind, and struggle to achieve this Utopian state through top-down social engineering: for example, marshaling a Big Lie campaign that "30 is the new 20" -- a phrase that gets 25,000 Google hits -- spreading propaganda about how older women have higher sex drives (they do not), and burning at the stake any man who would rather taste the flesh of a bright-eyed 22 year-old intern than that of a 48 year-old aspiring senator who graduated from Yale Law School.
Older woman #1 and I were in the same small Arabic language class, where I noticed her mock-flirting with me anytime we worked in pairs. She stood barely 5'0 tall and must have weighed under 100 lbs. Plus she was half-Persian and half-Pakistani, and these women age incredibly slowly (especially Persians). I recall bumping into her many times over the next two years on campus, and she always had an aristocratic aloofness to her -- not a false, bitchy sort of aloofness. Being a foreign medical student, she did not appear nearly as haughty as her American-born Brown peers.
After awhile, I figured why not ask her out -- she told me that she was 27 and preferred to date guys her own age (I was 20). Fooled! I tried to save face by saying something like, "Oh, if I'd known that you were that old, I probably wouldn't have asked you out." And how did she respond to this assholish remark? By apologizing for how young she looked, saying that she still gets carded at bars, etc., ending her email with a smiley face, and becoming more mock-flirty in class.
Even if an older woman is not magnetically drawn to a younger guy, she may still find him promising enough to want to initiate him into adulthood -- not necessarily by seducing him, but at least giving him some valuable sparring practice with a gorgeous female, to groom him for when he reaches full potential. Even attractive teenage girls will engage in this play-flirting with pre-pubescent boys who they sense are a natural lady's man, something I saw at my tutoring center, in the same way that high school athletes will invite the precocious fifth grade boy to toss the football around with them.
Because this behavior of older women toward younger guys is perfectly natural, it should be explained to the guy so that he understands that it is only for practice. If his hormone-soaked brain gets the better of him, as it surely will without being told otherwise, he will think her advances are genuine, and her eventual rejection will leave a sour taste in his mouth regarding girls, as though she were just toying around with his mind. There's probably a small, unstudied tribe of people living somewhere in France who discuss these relationships more openly, but here they may embitter more than they empower.