12.21.08 I made it with blue cheese for Yifan's wedding and it turned out very good! I also learned the difference between really good prosciutto (thin, fatty and not salty--when cooked, it's really crisp and tasty. $13.99 for 24 slices at costco) and bad prosciutto (the smoked kind from Trader Joe's that's much cheaper...$3.69 for 10 slices...). If you use the good stuff, you can wrap all you want and not have to worry about it being too salty, but really, one wrap over it and you're good.
To save room in the tray, we stabbed the date only through one side so that the date could be the base, but it cooks better if you can put the toothpick all the way through and rotate the date in the pan.
Also, if you use the fatty good stuff, make sure to work the prosciutto in batches so they don't get all melty and fatty.
Dates, pitted and halved ($4 something/pound at Henry's)Stuff date halves with either crumbled blue cheese or crumbled coat cheese. With the widest part of the prosciutto slice facing you, cut into about 4-5 1x1" pieces. Wrap each date, long ways with the prosciutto; there should be enough meat to wrap the date at least once around. Secure with skewer or toothpick.
Goat cheese (or blue cheese $7.89 for a tub at Costco)
Prosciutto ($13.99 for 24 slices @ Costco of good stuff, $3.99 for 6 oz @ TJ's)
Toothpicks or bamboo skewers
Grill or heat in an un-greased cast iron skillet for 45 s on each side or until browned and drizzle with balsamic vinegar if desired.