DatingMyStepson 23.09.13 - Massage And More S1E1 (Sarah Taylor) Pristine Edge has convinced her stepson, Jimmy Michaels, to date four of her milf friends plus one mystery lady in an effort to hook him up with a girlfriend. In this episode of Dating My Stepson, Sarah Taylor is the lucky lady who gets to date Jimmy first. The date that Pristine has arranged is a couple's massage.