While on a weekend trip to her old college town, 41-yr-old Elaine met 39-yr-old Leo through a mutual friend.  Feeling like she made missteps landing her in the just-for-fun category, Elaine is anxious about the possibility of Leo ever seeing her as wife/mother material.  On this episode, Paula explains how trying to control the category in her initial interactions rendered Elaine confusing to Leo rather than making wonder, and the decision Elaine needs to make to set things with this potential Mr. Right on the authentic right path.