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For top of glass, cut one heart cookie from 5 in. heart cutter. Trim 1 1/4 in. off top. For base of glass, cut remainder of trimmed cookie in half. Bake and cool both pieces.
Use smallest heart from Valentine kit to mold red candy heart; refrigerate to set and unmold.
Outline both cookie pieces with light pink melted candy in cut parchment bag; let set.
Attach heart candy to lollipop stick with melted candy; let set. Attach to bottom of glass with melted candy.
Tint piping gel light rose and smooth over glass and candy heart.
Attach cookie treat glass stem to backs of cookies with melted candy; let set.