Someday, when I own a restaurant/bed & breakfast/dinner theatre in some little New England town, I will offer a dessert item consisting of a stack of Oreo cookies and milk.

The first (but not the most crucial) question is: regular or Double Stuf? It goes without saying that the Oreos must be chocolate with white filling (“traditional” style), but the question of how much filling is trickier. If there were no such thing as milk, it would be easy – Double Stuf, hands down. If all dunked Oreos took milk consistently, then regular would be fine. The confounding thing about Oreos (and one of the most interesting things about them, actually) is that there are many subtle variations in the density of the chocolate cookie that combine to impact the amount of filling one might want in any given bite. The ideal solution would be somewhere between the single and Double, but of course that would be a custom job. Let’s put this issue on the shelf for now.

The second choice is: what kind of milk is best? It has to be cold milk (but not so cold that the tips of your fingers freeze when you dunk.) I could offer a choice, but my customers might want a recommendation from an expert… Skim milk is little more than murky water; what’s the point? Whole milk is too rich (note a similar problem with root beer floats – the very best ice cream and the very best root beer combined don’t make the best root beer float, because the combination is too much.) So I’d go with a nice cold 2%. 8 ounces in a wide mouthed cup is best – if the cup isn’t wide enough one can’t dunk effectively, if it’s too deep one risks losing a cookie, and if it’s too shallow the entire Oreo can’t be submerged.

Dunking Oreos is a primal pleasure, and an art. Fingers must be clean, and one should never mix hands – keep the same dunking hand until finished. Grasp the Oreo between the thumb and first two fingers; keeping the cookie vertical, quickly dunk the entire cookie in the milk, releasing on the downstroke. The cookie should gently touch the bottom of the glass and return to one’s grasp. Next, various advanced techniques can be added: the “spinning wheel” (rotate the cookie in the milk like a wagon wheel); the “new moon” (let the cookie lie flat in the milk, and flip with a quick downstroke of the index finger to allow both sides equal coverage); and the “dribble,” wherein the cookie is “bounced” repeatedly off the bottom of the glass.

Now… how long does one dunk an Oreo? There is much controversy amongst the uninitiated, but little debate between Oreo purists: as long as it takes. The perfectly dunked Oreo will begin to sink in the milk. At that precise moment, the Oreo should be removed from the milk and eaten in one bite. The very best Oreos will show a telltale pattern of bubbles that taper off as the cookie becomes properly saturated. (Be careful not to perform a “new moon” on a perfect Oreo – as likely as not, it will be lost to the bottom of the glass.) Strangely, the very best Oreos only happen every fifth or sixth cookie (the ratio seems to be 1:5.5.) It is the anticipation and hope for these gems that Oreo connoisseurs keep eating for. Still, Oreos and milk are much like sex (and some would say pizza, although I’m not sure about that): even when they’re not great, they’re still pretty good. (It should be mentioned that “Oreo” is not a generic term: the cookies must say “Oreo.” Hydrox and other store brand knockoffs are inferior and should be avoided at all costs.)

How many Oreos is too many? The funny thing is that they all taste great until the very last one – you’re not aware you’re going too far until you’ve gone. Experience should dictate how many is enough – after a full meal four might be satisfying, but the average for Oreo lovers seems to be six; in my restaurant, I will offer seven. No doggie bags – Oreos don’t last long in the wild, and zip-lock bags give them an unpleasant plastic flavor. When the last cookie is dunked, wipe fingers on a napkin. Drink the milk in a long (yet civilized) draught – this is the crown of the dessert. Wipe corners of the mouth with the napkin. Digest.

You can hear this piece in Podcast Episode #6