Preheat oven to 350˚ F.
Slice tops off of the garlic, toss with the olive oil, then put the heads, tip-side up, in a small baking dish and cover loosely with foil. Bake for 25 to 30 minutes or until garlic is soft and tender. While garlic is roasting, boil or steam potatoes until tender. Drain well. Cool the garlic and squeeze out pulp. Mash pulp with a fork until puréed.
Mash the hot potatoes while mixing in the butter. Beat in the hot milk gradually, mixing until soft and smooth. Stir in the roasted garlic purée. Add salt and pepper to taste. Transfer to a warm serving dish, and garnish the dish with parsley and chives. Serve immediately.
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