In advance, make first Cupid. For head, tint a 1 1/2 in. ball of fondant orange/pink combination; add a pinch of Gum-Tex. Roll out fondant 1/8 in. thick and cut with medium round Cut-Out. Let dry on cornstarch-dusted surface. Use tip 3 and royal icing to pipe string mouth and dot eyes, nose and cheeks (flatten and smooth with finger dipped in cornstarch). Position head on waxed paper; use tip 3 and royal icing to pipe curly hair; let dry. Cut lollipop stick to 2 in.; attach to back of head with royal icing; let dry. For right arm, roll small log of orange/pink combination fondant 3/4 in. long x 3/8 in. wide. Push 2 in. length of lollipop stick into arm leaving 1/4 in. exposed. Roll 1/2 in. fondant ball; form hand, add piece for thumb and attach to arm. For left arm, roll 2 in. fondant log measuring 1/4 in. wide at wrist to 3/4 in. wide at shoulder. Cut lines for fingers with paring knife; attach small thumb piece and position pick in hand.
Bake and cool cupcakes, ice and position head and arms.
In advance, make second Cupid. For wings, add a pinch of Gum-Tex to 1 in. ball of fondant, roll 1/8 in. thick and cut with 2nd smallest nesting heart cutter; let dry on cornstarch-dusted surface. Bake and cool cupcakes. Use tip 12 and orange/pink combination stiff buttercream icing to pipe ball body, pull-out legs and ball head (smooth with finger dipped in cornstarch). Position heart icing decoration and pipe tip 12 pull-out arms, tip 5 ball hands, tip 3 pull-out fingers. Use royal icing to pipe tip 3 eyes, nose, mouth and hair. Attach heart wings to back with icing.