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Find a date to a bluegrass concert in the Bluegrass State of Kentucky. Relationships are a two-way street, start searching for your match today! Subscribe now and start emailing singles in Monticello, Kentucky today! Online Dating 101: Step one, create your free Match.com Monticello personal profile with your best photo; step two, watch your Monticello dating choices line up; step three, choose the date of your dreams.