The Five-Star Weekend

Posey checks her phone and stands up. “My Lyft is twelve minutes away. I’m going to the hotel to get my bags.” She looks at Nick. “You’ll take my clubs back to Chicago?”

“Posey,” Nick says in a tone that is part admonishing, part disappointed. But nothing follows. When Posey bends over to kiss her father’s forehead, he closes his eyes in defeat. “Wish Phineas good luck from us.”

Dru-Ann can’t believe this. Nick is as soft as a shoe full of shit.

Posey leaves Whine without so much as another look at Dru-Ann—Coward!—which prompts Dru-Ann to call after her, “Quitter!”

This, she assumes, is what motivates some nosy ass-clown at a neighboring table to whip out his phone and start filming. He captures Dru-Ann’s unfiltered rage as she rails at Nick. “I can’t believe you didn’t stand up to her. She’s leaving, Nick. She’s flying to Scotland. She’s going to tell everyone it’s a ‘mental-health issue’”—Dru-Ann uses air quotes—“when she needs to suck it up and play through!”


Now Dru-Ann watches herself shriek these words in a trim sound bite on three different Twitter accounts, including one that belongs to some dude with a million-billion followers whose only job appears to be posting on Twitter.

Dru-Ann clicks out of the app and storms upstairs, where her partners—all of whom are fed up with dealing with the whims of their entitled clients—will be waiting to talk her off the ledge.

But the offices of the J. B. Channing Agency are oddly subdued. Usually at this hour, everyone is gathered in the common area in front of the 105-inch television, watching SportsCenter. But today, the television is off. Dru-Ann blinks. Has she ever seen the television off? There’s always a sporting event happening somewhere in the world—cricket, soccer, rugby, polo, Australian-rules football—and chances are, a J. B. Channing client is participating. The blank screen is so unusual that Dru-Ann suspects a power outage—but all the lights are on.

Dru-Ann approaches her corner office with a sense of impending doom. All the office doors are closed. This never happens. The men Dru-Ann works with love to showboat the very important conversations they’re having—with Federer, with Davante Adams, with the PR people at Emirates airlines who want to feature Dwayne Wade in their new ad campaign.

Dru-Ann’s assistant, Jayquan, has her espresso waiting as usual, so apparently the apocalypse hasn’t arrived. Dru-Ann accepts the cup gratefully and Jayquan winces. “JB is in your office.”

Scratch that—the apocalypse has arrived.


J. B. Channing is a force in the world of sports. He founded this agency; he’s a five-time winner of Chicago’s Businessperson of the Year, and he’s perennially on the Ebony Power 100 list. Last year he appeared in People magazine’s Most Beautiful People issue; he dates actresses, and for a few months, he was sleeping with the most successful pop star on the planet. He has very famous friends. (Behind his desk is a photograph of him with Jimmy Kimmel, Jason Bateman, and Chris Rock; they were out together at the Green Door.) JB is not only Dru-Ann’s boss, he’s her champion. Like Dru-Ann, he graduated from North Carolina and then the Kellogg School at Northwestern. He hired Dru-Ann because they share two alma maters and because she has the best nose for talent that he’s ever seen. Dru-Ann is a fierce advocate for other women of color; she doesn’t tolerate nonsense, and she speaks her mind. She thinks only two things are more important than natural ability in an athlete: hard work and discipline.

JB has made it clear that he loves these things about her.

But not today.

He doesn’t even bother with a greeting. “The video is everywhere and, unfortunately for us, it’s a slow news day in the sports world.” He sighs and runs a hand over his shaved head. “There are very few hard noes in our business, Dru-Ann. But you can’t mess with mental health.”

“Right, I know. Except—”

“No exceptions. You were at the retreat with the rest of us.”

Yes, Dru-Ann was at the mental-fitness retreat at the American Club in Kohler, Wisconsin, which JB organized after a wide receiver from Baylor—a kid who had been drafted by the 49ers—committed suicide.

“I was defending mental health,” Dru-Ann says. “Posey whipped it out because it was convenient.”

“You’ve lost four clients already this morning,” JB says. “Tamika, Winnie, Nyla, and Linzy. More are sure to follow. I’m placing you on a leave of absence until this blows over, and Jim and his team are drafting your apology statement right now. We want to get it out as quickly as possible.”

“I’m not issuing an apology,” Dru-Ann says, “because I wasn’t wrong. Posey Wofford is mentally healthy. She’s using it as an excuse, JB.”

“You’ll issue an apology,” JB says, “or I’ll be forced to take the next steps.”

“And do what, fire me?”

“Obviously I’m not going to fire you, Dru-Ann,” JB says.

“Then defend me, please.” Dru-Ann gazes out the window at the skyline of Chicago, then turns on her stilettos. He wants a leave of absence from her, she’ll give him one.

“We’ll be in touch about the statement!” JB calls after her.





Dru-Ann retraces her steps to the womblike comfort of the Phantom and peels out of the garage (the attendant is dishing her attitude!). Like an automaton, she pulls onto Lake Shore Drive and heads north, which feels so wrong, so backward. She owns a beautiful brownstone in Lincoln Park but she doesn’t want to hang out there during the day.

Her phone rings and the posh British voice says, “Nicholas Wofford,” making it sound like Nick has appeared on the doorstep in a tuxedo with an armful of calla lilies.

“Accept.” Dru-Ann doesn’t really want to talk to Nick—this whole thing happened because of his terrible handling (and, let’s just say it, parenting) of Posey—but the sad fact is that Dru-Ann has fallen in love with him, and also, she’s low on friends. “Hey,” she says. “Are you at the office? Can we grab coffee?”

A silence follows, then Nick clears his throat and Dru-Ann thinks, Oh, dear God, no. Not you too.

“I think we should hit the brakes,” Nick says. “And not see each other for a little—”

Dru-Ann ends the call and screams into the rarefied air of her car’s interior. Is it possible that absolutely everyone in her life has abandoned her? A text comes in and Dru-Ann assumes it’s Nick offering some feeble, patronizing words, but when Dru-Ann checks the display, she sees it’s from Hollis. Colors for our outings this weekend, it says. Dinner Saturday: black or white. Lunch Sunday: orange or hot pink.

That’s right, Dru-Ann thinks. Nantucket. She had intended to cancel. She’s pretty sure Hollis was expecting her to cancel—not for mental-health reasons but because Dru-Ann just plain old-fashioned hates the idea of any kind of girls’ weekend, especially one where they’re all wearing the same damn colors in public.

But Dru-Ann is so relieved that there’s a place she’s actually welcome that she calls Jayquan and asks him to book her a first-class ticket to Nantucket for the morning.

“Am I using the corporate card for this?” Jayquan asks.

Dru-Ann is tempted to say yes just to piss off JB, but the last thing she needs is an inquiry from Accounting. “Personal card, please,” she says. “And arrange for a car service on the other side to take me to a place called Squam Road. Put my e-mail on OOO until further notice.”

When Dru-Ann hangs up, she feels a tiny bit better. She’ll pull her hot-pink Stella McCartney bodycon out of the back of her overflowing closet; she will slurp the oysters and dance on Hollis’s deck in the moonlight.

She will slay the girls’ weekend. She will be the MVP.

Nantucket, she thinks, here I come.





7. Poet’s Corner


It’s a Thursday afternoon in the Poet’s Corner neighborhood of Wellesley, and Brooke Kirtley is cropping and editing a photo of herself to post on Facebook.