Smarties - Mateus Rosé. Both are slightly fizzy on the tongue and a Rosé won't overpower the Red Dye No.3.
York Peppermint Patty/Junior Mints - A Castilla y León that you can buy at a gas station.
Dum Dums - An Old Fashioned. Skip the garnish and use the lollipop as a stirrer. You're the fun