There are so many reasons to love them. They're delicious. They're rich in history. They're filled with frosting.
What they are not, however, is the successor to King Cupcake's place in the popular dessert kingdom--regardless of what the New York Times says. Now, I realize that this is a powerful claim--but it's not just talk. To really become the next big thing, Whoopie Pies have some work to do. Let's lay it down:
Problem one: The Stupid Name. There's no delicate way to say it: Whoopie Pie is a stupid-sounding name. For me, "whoopie" conjures up goofy images of sexual reference on the Newlywed Show and cushions that make farting sounds. I don't know about you, but even adding "pie" after it doesn't serve to cancel out these associations or change them to "irresistible dessert".
Is there a solution? Well, changing the name. Easier said than done, as anyone who has tried to upgrade to a full name from a diminutive knows; however, may I humbly suggest a few new names, just to try on for size? Frosting sandwich? Sweetburger? Cakewich? They may not be perfect, but no worse than whoopie pie.
Problem two: the cute factor. Don't get me wrong--whoopie pies do have a certain visual charm. But they're kind of cute in the same way my pug is cute--a sort of ugly-cute. They are a little lopsided, and the ungarnished cakey bits aren't much to look at on their own, and the look is generally very homey. Not to say homey is a bad thing, but if they want to graduate to a dessert worthy of cult following and mentions in US Weekly, they're going to need a little work on their styling.
Is there a solution? Luckily, there are remedies. I thought it was very cute to add sprinkles, nuts or chocolate chips to the side, chipwich-style, as I saw at Seattle bakery Sweet on You; the delicate frosting piping shown in the New York Times article index photo (whoopie pies from Trois Pommes Patisserie in Park Slope) adds a pretty touch too. Also, playing with flavor (as Joy the Baker, Crumblycookie.net and Seattle coffee shop Javasti have done) can also be a very effective way to not only add to the deliciousness of the treats but also to add some stunning color contrasts which lend an air of sophistication.
Problem three: the size. They are, to put it delicately, huge. As much as it pains me to say it, the classic whoopie pie is often too huge for a single serving, which poses the eater with all sorts of awkwardness. Do you share with a friend? Do you save it for later? Either way there are obstacles--if you're sharing, you've got to first face the issue of whether or not you really want to share, in addition to the more practical matter of how to divide it, especially if you've taken it to go. If you've decided to save it for later, you're left carrying a somewhat delicate confection which can easily crush or ooze so that you lose precious frosting. This is a serious bummer.
Is there a solution? Mini whoopie pies. I first encountered these at the Baked: New Frontiers in Baking book party in Seattle, when they served mini versions of their insanely delicious pumpkin whoopie pies. At about 2.5 inches in diameter they were the perfect single-serving size, with a great frosting-to-cake ratio and no awkward "want to share?" moments.