It's a thrill to serve this one up, but making it is almost more fun! You layer three elements — whipped cream, pound cake and raspberry sauce — in a wineglass to make one delicate and slick looking dessert. Driving your spoon through all those tempting layers and pulling out a mouthful of sweetness is just about as much as a date can take. My favorite part of making the dessert is using the wineglass to cut out the cake circles. It takes me back to the days of pressing out Play-Doh cookies at preschool. Admit it, those were some good times! Anyway, the size of your wineglass is important: one that's much narrower at the top than at the middle won't work well because you'll wind up with cake circles that don't fill out the body of the glass. So choose a glass with pretty straight sides.
In a small bowl, whisk together jam and water, set aside.
Cut the pound cake into thin slices about 1/8-inch thick. Take one of the wine glasses that you will use to serve the dessert in and cut out a circle from each slice of cake by pressing the rim of the glass into the cake. When you're done, wash the glass.
In a large mixing bowl, whip the heavy cream with a whisk or electric mixer until it just begins to hold soft peaks when you pull the beaters out. Sprinkle in the sugar and continue beating to soft peaks.
Drop a couple of large spoonfuls of the cream into 2 wine glasses then press in a cake round followed by a thin layer of raspberry sauce. Repeat until you've almost filled the glass. End with a layer of cake, then cream and then drizzled berry sauce over the top.