Failure to Match: An Enemies to Lovers Billionaire Matchmaker Romance

“Sixty-seven failed matches. Sixty-seven.”

I knew it was coming, yet I still flinched when the leather folder slapped the oak conference table.

You’d think I’d be used to it by now. Alice and Mitch both seemed to be.

“How is it possible that you haven’t been able to find a single appropriate match for the only client that actually fucking matters? How? What the fuck am I paying you three for?”

It was a trick. You weren’t supposed to answer her.

“Someone answer me. Now.”

My gaze dropped to my lap, which was a mistake. The only thing Vivian Hale disliked more than an incompetent employee was a spineless one.

Sure enough, the nanosecond I cowered, her attention zeroed in on me, her neck tugging back like a viper preparing to strike.

“Jamie,” she snapped. “You’ve been keeping awfully quiet today. Care to chime in?”

Not even a little, no. What was the point when she wasn’t willing to listen?

Still, I lifted my chin and set my shoulders back. I had my answers memorized by this point. It was just a matter of reciting them.

Here was the thing—Vivian didn’t actually want an explanation as to why we’d spent the last eight months failing to do our collective jobs. She didn’t really want to hear why we were struggling to find a suitable match for (arguably) the most eligible bachelor in North America and (inarguably) her most high-profile client.

If Vivian wanted real answers, she would have listened to us half a year ago when we’d warned her this might happen.

The only thing the CEO of Charmed Elite wanted to hear was yet another lie about how we had A Very Thorough Action Plan in place to address The Issue and were this close to getting her results. Because at the end of the day, failing to find a match for Jackson Sinclair would be irrevocably detrimental to the reputation she’d spent twenty-odd years building—the one that had her hailed as the number one matchmaker in the world.

The industry was small, and the Sinclairs were… well, they were The Sinclairs. One of the wealthiest, most influential families in the country. Money talked, and word of mouth was everything in this business. If we failed, rumors would spread that Vivian had lost her touch, and our competitors would start circling our existing clients like vultures, waiting for the inevitable exodus that would follow if Minerva Sinclair decided to take her business elsewhere.

The super fun part? Vivian was flat-out in denial. She didn’t want to accept that we’d already failed, which was why Alice, Mitch, and I had spent the last few days brushing up our résumés instead of working. Because when this whole thing ultimately blew up, Vivian needed someone to blame. Getting fired was an inevitability.

Clearing my throat, I shot her a reassuring smile and⁠—

“It’s not us.”

My mouth snapped shut, my eyes flaring as they darted to Alice.

Vivian’s neck slooowly rotated in her direction, her glare lethal. “What?”

“It’s not us, Vivian,” Alice repeated calmly. Too calmly. She sounded almost bored. “It’s him.”

Mitch and I exchanged questioning glances as Vivian let the silence stretch, daring her to go on.

Alice wasn’t deterred, though. Instead of shutting up, she lifted an unapologetic shoulder and let it fall. Not for the first time, I was convinced she didn’t experience fear the way the rest of us did. Likely due to her upbringing.

I’d feel invincible too, if I had her financial safety net.

“He’s impossible.” She held Vivian’s glare with unbothered ease. “Jamie tried to warn you this would happen six months ago, but you didn’t want to hear it.”

Mitch jerked beside me, kicking Alice under the table from the feel of it. He was ignored.

Inspired by her no-fucks-given approach, I sat up a little straighter.  Maybe today was the day. Maybe this time Vivian would listen. “Viv, there are less than a hundred single women in the entirety of North America that meet his criteria and, as of yesterday, he’s turned down sixty-seven of them.”

“So?”

I thought that part was pretty self-explanatory but okay, I could spell it out for her. “We don’t really know what else you want us to do. Mitch and Alice have been working nights and weekends to find appropriate matches for his standing appointments, and I’ve been staying late to do damage control on the carnage of angry tears and bruised egos he’s leaving behind. We’re tired.”

“Chances are good we’ll run out of candidates before we find him a partner. It’s not us, it’s him,” Alice reiterated. “Jackson Sinclair doesn’t need a matchmaker, he needs a miracle worker. And a really good therapist, if I’m being honest.”

Mitch shrunk an inch in his seat.

“And?” Vivian pushed. “What’s our plan? How do we work around these obstacles⁠—”

“We don’t. We fire him,” Alice countered smoothly.

This time when Mitch jolted, he managed to kick her hard enough to earn himself an irritated glare.

Vivian’s lips twisted into a sneer-like smile as she stepped up to the table. My stomach crumpled. “Your proposed solution is to fire Jackson Sinclair as a client? Do you have any idea what that would do to our reputation? Half of our active accounts joined after Minerva announced the partnership at her luncheon. What do you think will happen if she takes her business somewhere else?”

They’d probably run into the same issues with him that we had. I bit my tongue; Alice didn’t.

“Again, we told you this might happen, right after he sent one of his assistants to do the onboarding interview on his behalf,” she said. “We still haven’t actually met him in person.”

Vivian waved a dismissive hand and started to pace again. “Not taking him on as a client wasn’t an option. And firing him now is out of the question. What I need from the three of you is a solution.”

“That’s the problem, we don’t have one,” I said. “We’ve tried everything short of Immersive, and that’s only because he won’t agree to it.”

A blessing in disguise if you asked me. Not that I was senior enough to even be considered for the role, but I couldn’t imagine being stuck to Jackson Sinclair’s hip like that for an entire month, knowing what I did about his file.

The Immersive Coaching Package was normally reserved for our most challenging clients. They were assigned a full-time relationship consultant and dating coach who spent four weeks studying their daily life, routines, behaviors, and habits, then used the gathered data to find them a suitable match. The whole thing was very intense.

The assigned consultant was even required to attend their dates and observe them from a distance so they could “coach” the client afterward if required (which, nine times out of ten, if a client’s situation was critical enough to warrant an Immersive, then coaching was definitely required).

“I’m with Jamie,” Alice said. “Unless he’s willing to bend on some of his criteria and spare us a bit of his time, then we’re all out of ideas.”

Vivian crossed her arms, but instead of lashing out, she granted us a single firm nod. “All right. I admit that his rigid schedule and expectations for a partner make this more limiting than we might like, but it’s not impossible. Failure isn’t an option here—it just isn’t. We have to find a way to work around it.”

Again, denial.

I slumped back in my chair, but Alice stood firm. If anything, Vivian’s reluctance to see the reality of our situation only fired her up. “We’ve done everything we can with the information we’ve been provided. Sixty-seven women miraculously met his insane criteria, and not one of them was able to secure even a second date with him. Not one. Our data has to be flawed for that to happen but, again, he refuses to partake in our assessments himself, so we’re stuck working with what we have. All his tests, questionnaires, and interviews were done by his staff, and some of them weren’t even fully filled out. His team is dictating what information we need to do our job, and it’s just not working. There’s a reason we wouldn’t have made these exceptions for someone with a different last name, Viv.”

I was half-convinced that Jackson didn’t actually want to find a partner, but I couldn’t figure out why he’d waste so much of everyone’s time and resources, including his own.

The sign-up fee at Charmed was a hefty seven figures, not to mention the level of initial commitment our programs required. The company catered to the top one percent of the one percent, and if there was one thing our clients had in common (apart from their incomprehensible wealth) it was that they didn’t like wasting their own time. That was why they hired us in the first place—to do all the vetting and hard work for them.

“Why?” Vivian asked, her sharp gaze snapping among the three of us. “Why haven’t they been able to secure a second date with him?”

“Your guess is as good as ours,” I said.

“What does that mean?”

I edged forward in my chair. “The feedback we’ve been getting from his team has been vague and confusing, so we really only have the women’s version of events to work with. But that doesn’t help since we need to know why he didn’t think the dates went well.”

His matches never voiced any complaints about the experience, and most of them were quite upset after being told that Jackson didn’t want to pursue anything further with them.

Another thing a good portion of our clientele had in common? They weren’t used to rejection, and some of them did not know how to handle it.

Vivian nodded again, and for the first time since we’d been assigned this hellish nightmare of a case, it felt like she was maybe hearing us.

“Okay,” she said. “So then, there you go. That’s your next step.”

I frowned. “What is?”

“You need to figure out what’s really happening on those dates.”

There was only one way I could think to do that, but she wasn’t going to agree to it. “Could we maybe sit in on one of your meetings with Minerva and see if she has any insight⁠—”

“Out of the question.”

Then I was out of ideas.

Mitch nudged at his wireframe glasses, finally deciding to take the baton. “Vivian, we’re really not exaggerating. He won’t even get on a five-minute call with us. And since he hasn’t signed off on an Immersive, we can’t exactly send someone out to observe the dates…” He trailed off when Vivian started to shake her head.

“No,” she said. “Try again. He’s not going to budge on his schedule. Think of a different way. You need the data, so how will you get it without his cooperation?”

“We’ve spent eight months trying. He won’t—” Alice cut off abruptly, her eyes going in and out of focus. She sucked in a short breath. “Oh.”

Oh?

Oh, what?

But before I could ask, Vivian cleared her throat and smoothed down the front of her pleated dress. “Figure this out, and soon. I don’t care what you have to do to get me results. Minerva is running out of patience and if she decides to take her business elsewhere, half of our portfolio will follow, and that’ll mean layoffs. Period.”

She shot Alice one last knowing look on her way out, the opaque glass door sliding shut behind her.

“Holy shit,” Mitch breathed, his upper body practically collapsing on the table. “The fucking balls on you, Alice.”

She glared at him. “The next time you decide to play violent footsie with me under the table, don’t. You almost ripped my tights with that last kick.”

“I was trying to save you from yourself. Vivian looked like she was ready to fire you on the spot when you started talking back.”

Alice rolled her eyes. “She’s going to fire all three of us anyway. She knew exactly what an impossible clusterfuck this was going to be from the very beginning. Why else would she assign three junior consultants to a client this important instead of taking it on herself?”

“Because we’re young, ambitious, and willing to put in the long hours it requires?” Mitch tried.

“No. Because we’re young, naive, and disposable.”

“That’s incredibly depressing,” I said.

“It’s reality.”

I slumped in my chair with a sigh. I really didn’t want to lose this job—not after I’d worked so hard for so long to get it. Charmed was the crème de la crème of matchmaking companies, so anywhere I went after this would feel like taking ten steps back in my career. Not ideal.

Before Jackson Sinclair, my professional life had been perfect. I’d loved my job, the people, the work-life balance, and even Vivian hadn’t been so bad when we weren’t constantly disappointing her.

I swiveled in my chair. “You know… if we get fired and have to look for new jobs, we’re going to need to explain why we weren’t able to find a match for a literal Sinclair.” The industry was small, and people talked. It was bound to get out. “They’re all going to ask.”

Mitch shoved a rough hand through his hair. “I’m more worried about tomorrow night. We have no one to send to Jackson’s standing appointment, and I doubt we’ll find a match in less than thirty hours. If we have to pull another all-nighter and sleep here, I’m gonna lose my fucking mind. I can’t do it.”

“Also, how the hell does she expect us to get unbiased data on the dates?” I looked between the two of them. “Drones? Hacking security cams?”

“I have an idea that’ll take care of both problems,” Alice cut in. “But you’re really not going to like it.”

“No. Absolutely fucking not.” No way. There was no way I was willing to do it.

Alice leaned in, arms flattening on the table. “Come ooon. It won’t be that bad.”

Was she serious? “You want me to go on a date with Jack the fucking Ripper and you don’t think it’ll be that bad?”

“It’s not like you’re going as yourself,” she argued. “You’ll be undercover.”

“How is that not a thousand times worse?”

Not only was it a terrible idea that would undoubtedly blow up in our faces, but I was the absolute worst person for the job. I hated lying. It made my insides itchy, and the upkeep was almost always too stressful to be worth it.

“Don’t overthink it,” she said. “We’ll hook you up with some discreet surveillance equipment and give you a solid fake profile. You’ll be fine.”

“You’re really not thinking this through,” I told her.

“Agreed.” Mitch tapped his knuckles on the table. “Too many things could go wrong. Plus, there would be absolute hell to pay if Jackson ever found out.”

Right. Exactly. “Not to mention I don’t meet any of his physical requirements.”

I was blonde, five-foot-seven, and twenty-eight.

Jackson Sinclair only dated brunettes between the ages of thirty and thirty-six, and they had to be at least five-foot-ten. His last match (number sixty-seven) was a former Miss World winner and current CEO of a major PR company. He’d take one look at me, turn around, and leave. Just like he had with Allison Park (number twenty-nine), who’d then spent a full hour screaming at me over the phone like it was somehow my fault.

After that, Vivian had called Minerva to ask that Jackson at least respect the one-hour requirement Charmed had for all first dates, the point of which was to ensure our clients gave their matches an actual chance.

Alice shrugged. “We’ll get you a wig and a pair of platforms, put you in a dress long enough to cover your feet, and have you arrive early so you’ll be seated by the time he gets there. He’ll be none the wiser.”

“If it’s that simple, why don’t you do it?” I challenged.

“I’m five years younger and two inches shorter than you, Jamie. Even if you put me in heels high enough to meet his stupid height requirement, I wouldn’t be able to walk in them. Plus, you’ve been doing this for a lot longer than I have, you have a ton more experience dealing with clients, and you’re kind of amazing at reading people.”

Bullshit. “Gentle reminder that I was friends with Ria for a decade before she met your brother and didn’t realize her nostril flared when she lied until he pointed it out.”

They were now married—her brother and my best friend. That was how Alice and I initially met. I’d done this to her. I’d gotten her this mess of a job.

“You were too close to Ria. That’s your blind spot, but it won’t apply to Jackson.”

“I can see his face just fine on the screen if you’re wearing a camera,” I said. “And he probably won’t even notice your height if you’re seated⁠—”

“No,” Mitch blurted abruptly. “No, uh, that’s not… Jamie should do it. I vote for Jamie.”

Alice frowned at him. “What’s wrong with you?”

“Your torso,” he responded.Original content from NôvelDrama.Org.

“Excuse me?”

“Your… uh, it’s the height thing. Even if you’re sitting down, he’ll be able to tell… because of your torso. It’s… short,” he explained eloquently.

Alice stared at him for a full, wordlessly unimpressed minute before turning back to me. “There you go. I can’t do it; I’ve got a short torso.”

Mitch’s neck was purple.

“I don’t care. I’m not doing it,” I said. “I’m not.”

“Fine.” Alice let out a long breath. “Then I guess it’s back to the drawing board.”

Yes. Fine. Great.

We’d figure something out. We always did.

“It’s not like a bad torso. It’s just compact.”

She shot him another lingering what’s-wrong-with-you look before getting up. “I’ll grab us coffee. We’re going to need it.”

Mitch deflated the second she was gone, his forehead hitting the table with a sad thump.

“Smooth,” I said.

“Shut up.”