When Ben Fox's (Nat Faxon) niece, Maddie (Maggie Elizabeth Jones), declines to invite him to her school's Career Day, the brother half of the "Ben and Kate" brother-sister duo attempts to change Maddie's mind. In the process, he discovers something he does well.
Kate (Dakota Johnson) has been flirting with a single father since meeting him on Halloween. Her friend and co-worker. BJ (Lucy Punch). calls it "the saddest mating ritual ever," but Kate calls it "Operation Crock Pot," because she's taking things slow: finding excuses to run into him and flirt.
Ben, however, wants to do recon on the prospective boyfriend and find out if he's "worthy of the Fox name." So when he sees Will (Geoff Stults, previously of "The Finder") at school with his daughter, he approaches him.
With the help of Tommy (Echo Kellum), Ben goes through a list of career opportunities and is reminded of some crates of wine he's been storing, sent to him by a former girlfriend. Naturally, he brings them to the small house, stacking them in the kitchen and living room. When Kate is dismayed by the clutter, Ben also springs the news on Kate that he's invited Will over to grill (and presumably to be grilled, as well). Will has a good time and, upon leaving, invites Kate out for a date.
The efforts to become a wine merchant are not panning out, as Tommy's calls to wine bars fail to win them appointments. When some girls from an unidentified youth group sell them cookies at the door, they hit on how to sell wine without any contacts. They take the wine door to door, flirting with the housewives who answer.
When Will arrives for the date, Ben tells him to be good to Kate. In the process, he includes specific details, like the fact that she's afraid of people leaving her and hasn't had sex in a long time. This puts Will on edge.
Ben, who's hosting a wine tasting at home, learns from the invitees that Will had left his wife at Christmas time. So he bursts into Will's home, interrupting their first kiss. Will admits that he had left his wife three weeks before Christmas because she never put their daughter first.
Because of this, Kate later relates: They talked about his divorce and their childhoods. She's grateful that Ben helped them to reach that level of honesty so early.
Though he considers the wine merchant attempt a bust, Ben goes to school anyway and talks about not always knowing what you want to be. But if he'd thought of it, he could have told them one thing he does well: looking after his sister.