 In the episode , Liz Lemon ( Tina Fey ) finally dumps Dennis Duffy ( Winters ) and prowls the singles scene , where she proves to be particularly inept at picking up guys , under Jenna Maroney 's ( Jane Krakowski ) tutelage . Meanwhile , Tracy Jordan ( Tracy Morgan ) and James " Toofer " Spurlock ( Powell ) clash , landing both in sensitivity training , and Jack Donaghy ( Alec Baldwin ) dates a certain " high @-@ ranking African @-@ American member of the Bush Administration . " 
