Scott Foley gest stars as Jeff, a very wealthy potential home buyer who is interested in one of Jules overpriced homes. Meanwhile, Ellie with reserves leaves the baby with Andy for a day to prove that she trusts in him.

Sara is a confident wine rep who sets her sights on Grayson; but is he strong enough to be her man? Meanwhile, when Ellie tells Jules she can't change past a certain age, Jules is determined to prove her wrong by giving up wine for a month; and Bobby's new dog poses some unwanted competition for Andy.

Jules is thrilled for the chance to take care of Travis after his first big break-up. But when Jules discovers the truth about the break-up, she comes to an unwelcome realization about herself. Meanwhile, Sara considers whether Jules threatens her relationship with Grayson and turns to Ellie for guidance; and Andy searches for any resemblance between himself and son Stan.

Jules and Grayson consider the notion of FWB, friends with benefits. Meanwhile Andy hires a nanny for Ellie, and Travis benefits from Bobby's unconventional plans to make some extra cash

As Jules adjusts to living on her own, Grayson unwillingly becomes the new object of her constant attention; Travis turns to Bobby for advice on how to redefine himself at college; and Ellie is determined not to be friends with her new nanny.

Grayson decides that it's the right time to tell Jules about what had happened between Laurie and himself. After Jules knows the truth she tries to project her anger at someone, but cannot decide at who. While Laurie professes hel love for Smith, and Bobby gets obsessed with watching a street performer swallow a sword, and Andy gets Travis to doubt Kylie.

It's Jules' 42nd birthday and that can only mean one thing: gift contest! Each year, Jules holds a contest to determine who gives her the best gifts, which Ellie always wins. This year, Laurie teams up with Grayson in an attempt to overthrow her. As Jules contemplates what to do for her birthday, Andy suggests a night of dancing. Meanwhile, Travis introduces Bobby to a Netti Pot, but not without its consequences.

Jules ends up asking both Ellie and Laurie to be her "co-maids" of honor because she can't stand to hurt anyone's feelings; and Grayson tries to ask Chick for Jules' hand in marriage formally, but Chick decides to have a little fun in the process.