After Linda (aka Peaches) is caught coming home late from a night out clubbing, Melissa decides it's time for her to start taking dating more seriously. While Linda meets with a professional matchmaker, Mike is taking some guidance of his own from a life coach. Mike takes the advice to heart but also elicits the assistance of his brother Frank. Frank gives his two cents in helping Mike break his "Situation" stigma by introducing him to seersucker jackets and volunteering to be his manager.
The high-spirited Sorrentino family sit down to a Sunday night dinner when Marc announces that Mike will be working a shift at their family-owned tanning salon. Who wouldn't want to see "The Situation" cleaning toilets!? Tensions rise as the brothers find that working side-by-side can take a toll on their relationship. Mike and Marc are able to set aside their differences when they take newly engaged little sister Melissa to try on her dream wedding dress. And while Melissa begins the journey of starting a new life, she has demons to deal with which linger from Mike's years of addiction. She and Mike sit down with Mike's life coach to talk about the toll his behavior took on the family, Melissa in particular.