On Monday, Dr. Vino asked if cupcakes and wine were an impossible pairing. We know from the bakeries doing cupcake and wine events, the answer is no, but so do others!
Ben Narasin at Wine Enthusiast Magazine write "Let them Eat Cupcakes (and Drink Wine)" all about this very topic, with specific pairing suggestions: (click through for more, including his overall favorite):
Peanut Butter Chip (Sprinkles) with Beaujolais (Georges Duboeuf Saint-Amour)
"It's like a decadent peanut butter and jelly," says Jessica Owens, a Bay Area venture capitalist. The fresh, fruit-forward, jammy Beaujolais complements the chocolate and peanut butter flavors, while the light mouth feel of the wine parries their denseness....
Lemon cupcakes and Sauvignon Blanc or New Zealand Style whites (Cupcake Vineyards Sauvignon Blanc and Anne Amie Vineyards Cuvée A Amrita)
The crisp, green, tart wine cuts the lemon's acid and reinforces the pound-cake flavors of the confection.
For a sweeter approach, a Tokaji (Royal Tokaji Ats Cuvee) provides a gentle sweet wash over the lemon's zest. Late-harvest whites also work well (Mer Soleil Late), both by complimenting and intensifying the citrus notes of lemon.
Carmel Variants (Bebecakes Latin Bombshell and Sibby's Dulce de Leche) with Sweet Oloroso Sherry (Dry Sack Solera Especial and Gonzalez Byass Alfonso)
The dry, sweet caramelized notes in the wine parallel the caramel and burnt-sugar notes in the cupcake. Flavors merge and mellow with an incremental sweetness and a heightening of peanut notes.
Images from Flickr (not directly related to above recommendations, but pretty photos of wine-themed cupcakes):
Red wine cupcakes with red wine chocolate ganache icing and vanilla sugar from Flickr user tawest64
Hazelnut Pear Ice Wine Cupcake: Hazelnut Genoise filled with a compote of pears poached in ice wine and vanilla, topped with a Chantilly cream that has been laced with an ice wine reduction by The Grand Bakery via Flickr