Jules tries to party hard like a twentysomething and ends up looking like a total fool, when even her best friend Ellie, told her not to do it. Travis discovers trying to avoid further embarrassment due to his father, Bobby, working at his school, can actually add to it. Jules gets as frustrated as she faces the physical limitations of her age.

Jules family and friends crash the 10th date with her new boyfriend, Josh. Ellie and Laurie help Jules realize that it's ok to be selfish once in a while, when Jules has a disastrous experience in bed with Josh. Meanwhile, Jules left Travis with Bobby, who has to be responsible and deal with his son.

When Jules inadvertently tells Grayson he's hot and he doesn't reciprocate, she's on a mission to get him to admit she's sexy. With a little help from Laurie and Ellie, Jules uncovers the ultimate burn to put Grayson in his place. Meanwhile, Ellie is feeling like she's lost her looks after the birth of Stan, and Bobby and Travis search for something to bond over.

Jules rues the day when her ex-husband, Bobby, and Grayson become fast friends over a mercy golf lesson that she organized to help boost Bobby's self esteem. Meanwhile, Laurie surprises even herself when she takes on a new client to prove her worth to Jules.

When Josh tells Jules he's in love with her, she knows the time has come to break things off with him. Unfortunately for Jules, she's not the best at ending relationships without hurting people's feelings, but thankfully she has the expertise of friends Laurie and Ellie to see her through. Meanwhile, Bobby, Grayson and Andy hit the links with money and pride on the line.