So, remember Will, that cute single dad that Kate (Dakota Johnson) bonded with on Halloween (you know—the one that guessed she was dressed up as Babe Ruth Bader-Ginsberg)? Well, she’s totally into him. She’s even initiated “Operation Crockpot,” by which she will subtly flirt with Will for three months, until—BAM!—they’re in a relationship.
Meanwhile, Maddie (Maggie Elizabeth Jones) informs Ben (Nat Faxon) that her school’s Career Day is coming up. Ben, despite having no career whatsoever, is hard bent on participating. That gives him and Tommy (Echo Kellum) approximately two days to create a successful business venture. After considering highly viable options like reviving the American railroad industry and inventing a biodegradable cell phone, they decide on becoming wine merchants.
But finding a job isn’t Ben’s only mission; he’s also determined to do some reconnaissance on Kate’s new man. Much to Kate’s dismay, Ben invites Will over for a nighttime neighborhood barbecue—with Will as the sole invitee. But although Ben’s advances could seem totally creepy (he forces Will to engage in intense eye contact as they sip wine together), Will still asks Kate if she’d like to go out to dinner with him sometime—alone. As usual, Kate partakes in some of the AWKWARDEST FLIRTING EVER, but manages to agree to Will’s invitation. It looks like the heat on “Operation Crockpot” is rising.
At first, Ben and Tommy can’t say the same for their wine-selling operation. But after a brief, totally contrived scene in which girl scouts sell Ben cookies, Ben and Tommy realize that they could successfully sell their wine if they became slimy door-to-door salesmen.
And because Kate’s neighborhood is apparently filled with lonely, sexually frustrated housewives, Ben and Tommy are actually a success. Their wine business gains such popularity that they decide to host a wine tasting in Kate’s kitchen.
But first, Ben must bid Will and Kate adieu before they leave for their big date. Ben, ever the over-protective brother, gives Will one of the most intimidating pep talks of all time, informing him that Kate gets spooked easily, and also that she hasn’t had sex in quite some time (57 months, to be exact, as we learned earlier in the episode).
The result? Will is totally nervous on the date, rambling incoherently. (It’s almost as cringe-worthy as Kate’s attempts at flirting.) Finally, he admits that Ben’s pep talk freaked him out, only to have Kate admit that—though embarrassing—the things that Ben said about her were true. And the whole humiliating situation ends up being an opportunity for Kate and Will to discuss their insecurities and their hopes for the future and blah, blah, blah, romantic.
But Will’s not safe yet. At the wine tasting, one of the housewives informs Ben that Will left his wife last year, on Christmas. Ouch. Ben’s reaction? RESCUE KATE FROM WILL’S EVIL GRASP.
Back at Will’s house, just as Kate and Will are about to kiss, Ben bursts in the door to break them up. Oh, and by the way, Ben’s also been followed by the fuming, jealous husband of one of the wives at the wine tasting. It’s like that scene at the end of “Crazy, Stupid Love” when all the characters turn up at the same place and fight each other.
After a quick talk to mollify the situation, Ben and Kate realize that Will only left his wife because she didn’t put their daughter first (so Will’s a good guy – phew!) but Ben still gets beat up by the jealous husband. You can’t win ‘em all.
Somewhere in this episode, there’s also a pretty random subplot in which BJ (Lucy Punch) is sensing animosity from the kitchen staff at the bar/diner/whatever that place is where she and Kate work. In the end, she realizes that the reason they hate her is that she never bothered to learn their names, and she doesn’t really feel bad about it. The end.
Oh, and Ben realizes that he doesn’t have a job to talk about at Maddie’s Career Day, but that’s okay! He makes a speech about not knowing what he wants to be yet, and how it’s important to try. And everybody learns a lesson, and that’s awesome.
Lines of the Night
“It’s got flavors of cherry…and cigar…and bark…” - Ben, trying to sell his wine
“It’s a tough industry to break into, especially if you’re unknown. Not unlike our experiences with the cliquey world of meteorology.” – Tommy
“Let’s call this operation reputation rehabilitation. Do we name too many operations?” – Kate
“It was also not my plan to be used as foreplay by a crazy couple that should only exist in the 70s.” – Ben
“Don’t worry about not succeeding, because trying is succeeding. Unless you’re trying to fail, in which case failing then is succeeding.” – Ben, making his speech on Career Day