When Katie's mentor and dear friend Tami moves to Westport, Katie wastes no time introducing her to her "A Real Mother" vlog viewers. Meanwhile, Taylor discovers Greg has been keeping an entertaining secret. 

Katie and Tami make fast friends with J.D., a luxury hotel manager whose promise of access to complimentary hotel rooms around the world sounds incredibly enticing. However, Katie's travel fantasy comes to a screeching halt when she learns J.D. is an aspiring first-time father who's counting on her for parenting guidance.