Chapter 1 #2
"You're younger than I expected." Cecelia's voice was cool, assessing. "Your portfolio is impressive for twenty-five, but it raises questions. Three career pivots in four years suggests either remarkable adaptability or an inability to commit. Which is it?"
Most interviewers eased into the hard questions. Cecelia apparently preferred going straight for the jugular.
Emmy opened her portfolio, buying herself three seconds. Inside were printed samples from her advice column, testimonials from wedding clients, and a market analysis of Boston's matchmaking industry. She didn't pull anything out yet. Just used the motion to center herself.
"I prefer to think of them as vertical moves." She met Cecelia's gaze. "Advice column to wedding planning to matchmaking—each one gets closer to the actual work. Understanding what people need from each other."
She paused, watching Cecelia's reaction. Still skeptical, but listening.
"Wedding planning taught me the gap between what clients say they want versus what they actually need.
I had a bride who insisted on a massive church ceremony because that's what her family expected.
What she actually wanted was to elope to Hawaii with ten people.
We did the Hawaii wedding. She cried—happy tears—the entire ceremony.
" Emmy allowed herself a small smile. "Her family got over it. "
"And now you want to be a matchmaker." Cecelia's tone was mild. "Or you want to help brides overcome the genetic load of family expectation and find their spines."
"The spine part was a side effect. What I actually want is to be in the room before any of that becomes necessary."
Cecelia leaned back. Emmy noticed she wasn't touching the portfolio yet. Either she wasn't interested, or she wanted to assess Emmy first, separate from the carefully curated materials.
"Elite Connections doesn't deal in advice columns or wedding logistics.
We broker partnerships between Boston's most successful individuals.
People who don't have time for dating apps or mediocre setups from well-meaning friends.
They come to us because we understand what they need before they do.
" She tilted her head slightly. "Can you honestly tell me you're prepared for that level of responsibility? "
Emmy pulled out her market analysis. Slid it across the desk with steady hands.
“I’ve spent the last several months studying Elite Connections' client base.
Your sweet spot is professionals aged thirty-five to fifty-five who've prioritized career over relationships and are now realizing they want partnership.
They're successful, selective, and skeptical of traditional dating because it's inefficient and often disappointing. "
Cecelia glanced at the analysis but didn't pick it up yet.
"They're also exhausted by the performance of modern dating.
The apps, the games, the constant wondering if someone wants them or wants access to their life.
What they need is someone who can cut through all of that and identify genuine compatibility.
Someone who can see past what they present to who they actually are. "
"And you can do that."
"Yes." Emmy didn't hesitate. "I'm good at reading people.
Not just the obvious surface stuff—anyone can do that.
But the gaps between what someone says and what they mean.
What they're afraid of. What they're not letting themselves want.
" She leaned forward slightly. "That's what matters in matchmaking.
Understanding the truth someone's not telling you—sometimes not even telling themselves. "
It was the truest thing she'd said—the part she usually kept folded up small, somewhere ambition couldn't trample it.
Cecelia picked up the market analysis. Flipped through it slowly. Emmy watched her face for any reaction and found nothing. The woman could have been reading a grocery list or a declaration of war—identical expression.
Finally, Cecelia set it down.
"Your brother is West Woodhouse. Wide receiver."
Emmy's stomach dropped. She'd known this was coming—how could it not?—but she'd hoped it would come later. After she'd established herself. After Cecelia saw her as Emmy first, not as someone's little sister.
"Yes."
Cecelia's fingers tapped once against her desk—the first fidget Emmy had seen from her. "Professional athletes are notoriously difficult to match. High-profile lifestyles, demanding schedules, and—to be frank—a dating pool that self-selects for people interested in status rather than substance."
Emmy nodded. West had dated a string of increasingly interchangeable women before meeting his wife, and exactly none of them had seen him as anything beyond ‘NFL player with good genetics and better salary,’ until Brynn.
"Elite Connections has been trying to break into the athlete demographic for two years. The market is there. The access isn't." Her milk bath acrylics tapped a staccato on the desktop.
Emmy's pulse kicked up. She could see where this was going. The shape of the opportunity forming before Cecelia even articulated it.
"Your brother just got married. Beautiful wedding at the Four Seasons—I saw the photos in Boston Magazine.
Shame, really. He would've been an ideal client.
The publicity from matching a professional athlete could open doors we've been locked out of for years.
One successful placement with someone like him, and suddenly we'd have credibility with an entirely new demographic. "
The comment hung between them. Emmy knew what she was supposed to say. Something about West's happiness. Something about how some things mattered more than business development.
But her brain was already racing ahead, cataloging possibilities. West had teammates. Friends. People in his orbit who were single, successful, and probably dealing with the exact same dating challenges Cecelia had just described.
"West has teammates." The words came out smooth. Confident. "Friends in similar situations who might benefit from professional matchmaking."
"Do you have relationships with any of them?"
This was it. The pivot point. The moment between her current life and the one she wanted.
The truth was simple: she didn't have relationships with West's teammates.
She barely had a relationship with West anymore, not since he'd moved to the suburbs with his wife and started his settled married life.
It wasn't anyone's fault—there were seven years between them, and though they always been close, it was just what happened when someone's life leveled-up and yours didn’t.
When you were still in the same apartment, still between things, still waiting for the version of yourself you'd promised everyone you were becoming.
But saying so would end this interview.
Except there was one person. Not a teammate, exactly—not the way she thought of teammates. Someone who had been at her family's dinner table more times than she could count.
Grant Knight.
West's best friend since college. Quarterback. Three-time league MVP. Team captain. Face on billboards. Zero interest in Emmy meddling in his personal life.
That was the problem. She'd known Grant her entire life—he'd been at their house since she was five years old, since West was twelve and Grant was the cool older kid from down the street who could throw a perfect spiral.
He'd been at every graduation, every holiday, every Sunday dinner her parents still set a place for him at.
He was so woven into the fabric of her family that she'd never once thought to look at him sideways.
Her brain had never filed him under anything except West's. Except for approximately two years in high school when she'd filed him under something else entirely, but she'd been sixteen and he'd been twenty-three and that particular folder had been very firmly deleted.
You didn't matchmake family. You especially didn't matchmake family you'd once had a teenage crush on that both of you pretended had never happened.
But Cecelia didn't know that.
"Grant Knight." The name came out like a completely reasonable thing to say. "We grew up next door to each other—our families are close."
All technically true. The Woodhouses and the Knights had been neighbors for years. Grant had been at Emmy's high school graduation. She'd been at his NFL draft party. They were connected through a decade of proximity and shared history.
What wasn't true—what was complete fabrication—was the implication that she and Grant were still close. That she had any claim on his time or attention. That she could walk up to him and say "hey, want to let me find you a wife?" without him looking at her like she'd lost her mind.
But Cecelia was leaning forward now, interest sharpening her features into something that looked hungry.
“The Grant Knight." She didn't say it like she was testing the name. She already knew exactly who he was. "Thirty-two. Unmarried. No serious relationships in the past three years." She paused. "You could get him to sign on as a client?"
Emmy's throat went dry. Her heart hammered against her ribs. Everything intelligent in her was screaming that this was a terrible idea, that she was about to promise something she couldn't deliver, that she should backtrack right now before this went any further.
But everything ambitious in her—everything that had been waiting for an opportunity exactly like this since she'd graduated college and realized her Communications degree didn't come with a roadmap—was louder.
"Yes. I can do that."
Cecelia considered her with blade-sharp eyes. Emmy watched the calculation happen, risk versus reward playing out in real time. She forced herself to breathe normally. To maintain eye contact. To look like someone who absolutely could deliver on this promise.
Finally, Cecelia reached across her desk for a business card.