Throw caution to the wind and see what it's like to Kiss Jessica Stein this week as we explore a movie that's both heartwarming and problematic by turns. The most important lesson we learn here is that mom always knows what's going on, whether she really wants to know or not. As Jessica explores a different side of herself, we discuss what it's like to go on that journey ourselves and how to figure out what you want (what you really, really want) - spoiler alert: it isn't always just one perfect shade of lipstick.