When Dougie and I were building the company, I became confident, decisive, always three steps ahead. That version of me could walk into a room full of investors and convince them to write seven-figure checks. She could make split-second decisions that affected hundreds of employees. She could project absolute certainty even when everything was falling apart behind the scenes.
But that Blair doesn't exist anymore. Without a company to run, without crises to solve, I'm just a woman with too much money and too much time. Playing Sailor seems like a nice distraction from my uneventful life.
My phone stays silent for the next hour. I shower, dress in the same clothes I've adopted since retiring—athletic wear. I could visit the Metropolitan Museum, take a spontaneous trip somewhere, call one of my few friends who aren't buried in work. But none of it feels worthwhile.
I've tried joining clubs, going to networking events for entrepreneurs, even dating apps specifically for high-net-worth individuals. But every conversation feels like an interview for a job I don't want. People want to know what I'm working on next, what my investment strategy is, whether I'm looking for partners in some new venture. Nobody wants to just have drink without an agenda.
I'm finishing my second espresso when inspiration strikes. If I'm going to play the role of a struggling woman who needs money, I should probably lean into the character. I pull out my phone and start typing another message.
Just realized I don't have a suit and can't afford to buy one. (Sorry, I don’t wear dresses) We should probably meet up to discuss that being part of my 'package.'
I hit send and chuckle. It's a calculated move—creating a problem that requires us to spend time together, giving me something to do while advancing whatever this strange arrangement is becoming.
This time, I don't have to wait long for a response. My phone buzzes within ten minutes.
Morning. Sorry about my drunk message. How much do you need for a suit?
I write,Around $300 for a rental, maybe? More if you want me to look like I actually belong at your sister's wedding.
The response comes back almost immediately:I’ll buy you one. Meet me at Bergdorf Goodman at 2 PM. Women's formal wear, fifth floor.
Bergdorf Goodman. Of course. She's not messing around with budget rentals or off-the-rack options. She wants me to look like a successful finance director, which means she's willing to invest in the costume. I'm curious about what this wedding is going to be like if she's this concerned about appearances.
Great! See you at 2, I reply, then add,I'm Blair, by the way.
5
OLIVIA
The revolving door at Bergdorf Goodman spits me out into the marble-and-gold sanctuary of Manhattan's most rarefied shopping experience. The air smells expensive—leather, perfume, and whatever woody scent they pump through the vents to make people want to spend money.
I'm fifteen minutes early, which is standard for me. Punctuality isn't just a virtue in my business—it's survival. When you're coordinating vendors, venues, and high-maintenance clients, being late means watching everything collapse like a house of cards in a hurricane. But today, being early also means I have time to second-guess this entire ridiculous plan.
What am I doing? I'm about to spend a small fortune on a suit for a complete stranger so she can pretend to be my girlfriend at my sister's wedding. She may just take off with the suit and sell it; I know nothing about Blair apart from that she needs money and that doesn't exactly inspire confidence.
The hangover from last night's post-event scotch session is starting to fade, replaced by a different kind of headache. The kind that comes from making impulsive decisions whileemotionally compromised. I arrived home at nearly 3 AM, exhausted but too wired to sleep. The adrenaline crash that always follows a major event hit me hard, leaving me staring at my phone and thinking about Emma's increasingly frantic messages about plus-ones and seating arrangements.
That's when I found the napkin with her number, still crumpled in my purse. Before I could talk myself out of it, I was typing a message I barely remember sending.
I take the elevator to the fifth floor and navigate toward the women's formal wear section with rows of dresses and suits in every shade.
A woman approaches me immediately.
"Good afternoon, may I help you find something?" Her voice carries just the slightest trace of a European accent.
"I'm meeting someone here at two," I tell her. "We're looking for a nice suit. The occasion is fairly informal, but I want my date to look smart."
"Of course. I'm Margaret. I'll be happy to assist you both. May I ask what the occasion is?"
"A wedding," I say. "My sister's wedding."
"How lovely. Will you be requiring a full ensemble? Shirt, shoes, accessories?"
Before I can answer, I spot her. Blair emerges looking exactly like expected—gray track pants, white t-shirt, gray hoodie, hair slightly disheveled. She's scanning the floor, clearly looking for me, and I feel a flutter of relief that she actually showed up.
I wave her over, and she heads toward us.
"Hi, Blair," I say as she approaches. "You made it. Thank you."
