"Romantically Challenged" opens with Eliot and Liz nervously awaiting the arrival of their daughter, Ashley and her outlandish boyfriend, Email. Eliot adamantly believes that in order to protect his daughter, she must sign a prenuptial agreement before rushing into marriage, a view feebly condoned by Liz. Hilarity ensues when Eliot's friend and lawyer enters the scene and the tenuous formality between Eliot and Email decomposes into death stares from the father, and the continuous presence of feet on the table from the future son-in-law.