Combine pudding and milk in medium size saucepan. Cook over medium heat, stirring constantly, until mixture comes to a boil. Remove from heat; cool; chill.
Combine water, sugar, and vanilla in a skillet. Cook over low heat, stirring until sugar dissolves and mixture simmers. Poach pears in simmering syrup until tender when pierced with.of knife. Remove from syrup; cool. Cook remaining syrup until it is reduced by half. Remove from heat; add grenadine.
When ready to serve, pour pudding mixture into a small dish are bowl. Arrange pears on large plate around dish. Spoon some grenadine sauce on pears. Serve remaining sauce separately. Makes eight servings