24. The Gift of Doubt
24
THE GIFT OF DOUBT
ALEX
"No." Connor snatches my phone away, interrupting what was definitely a crucial email about quarterly projections and not at all my fifteenth check of Mac's blog since she left my place at dawn. "You are not buying your girlfriend a corporate merger for Christmas."
"I wasn't—" I start, but Grayson cuts me off.
"He's right. Also, you can't give her stock options either." He guides me through Bellevue Square's designer shops, the upscale mall decked in holiday splendor that somehow makes me feel more inadequate about gift-giving. "Though according to SecureMatch's compatibility algorithms, successful professional women in their forties tend to appreciate?—"
"If you say 'practical assets with growth potential,' I'm deleting your dating app," Connor threatens. "Besides, after last night's dinner disaster, he needs something more personal than corporate assets."
"Last night wasn't a disaster," I mutter, though Mac's evasiveness about the blog still stings twelve hours later. "It was just... "
"A disaster," Grayson confirms. "Your midnight texts about 'trust metrics' and 'information security protocols' were very convincing. Especially the one at 2 AM asking if my AI could analyze writing patterns."
The Saturday afternoon crowd parts around us like we're carrying plague instead of American Express Black cards. Possibly because three tech CEOs trying to Christmas shop looks a lot like a hostage situation.
"I don't need help shopping," I protest as they steer me toward Cartier. "I have people for that."
"Yes, and Emma specifically called us because you tried to have her schedule a 'gift acquisition strategy meeting' this morning." Connor checks his watch – a much less expensive model than mine, chosen for function over status. "Face it, Alex. You're emotionally constipated and we're your romantic Metamucil."
"That's..." Grayson winces, "a terrible analogy."
"But accurate." Connor stops us in front of the jewelry display. "Now, what does Mac like? Besides exposing corporate inequality and making you question your life choices?"
"Real helpful," I mutter, but my mind flashes to last night – Mac perched on my kitchen counter, tension under her smile as I asked about the blog's increasingly detailed posts.
The way she'd redirected every question about information sources. The too-early exit this morning, leaving only a note and the ghost of her perfume on my pillows.
"Earth to Alex." Grayson waves a hand in front of my face. "You've been staring at that sapphire like it holds the secrets to corporate trust issues."
"I'm fine."
"Sure." Connor leans against the display case. "That's why you've checked your phone six times in ten minutes, and you're straightening your tie like you did before that hostile takeover in '19. "
"Remember when our biggest problem was convincing Alex to ask Jessica Martin to the Stanford Spring Formal?" Grayson muses. "Now we're shopping for the woman who threw champagne at him then stole his corporate-issue heart."
"Jessica didn't stand me up," I say automatically. "She had mono."
"For six weeks after mysteriously transferring schools?" Grayson raises an eyebrow. "Sure. And Mac didn't leave your place at dawn because something's wrong."
I turn sharply. "How did you?—"
"Your texts, remember? 'Gray, you up? Need to talk about information security.' Then at 3 AM: 'Your AI any good at analyzing trust variables?'" He scrolls through his phone. "Followed by what I assume was drunk coding because none of those algorithms would actually work."
"I wasn't drunk."
"No, just spiraling about corporate leaks and relationship trust issues." Connor drags us to Tiffany's, where a holiday display of diamonds catches the winter sunlight streaming through skylights. Seattle's latest snowfall has turned the world outside into a blanket of white, making everything feel magical and somehow more complicated.
"Mac wouldn't want diamonds," I say automatically, then catch myself.
"But you've thought about it." Connor's voice gentles. "About jewelry. About permanence. Even while you're freaking out about blog posts and information security."
"I—"
My phone buzzes. A news alert that makes my blood run cold:
"TECH TRUTH: Corporate Trust is a Myth - Why Every CEO is Just Another Wolf in Versace"
The post is brutal. Scathing. A complete departure from Mac's recent balanced critiques. This is an attack on tech leadership that feels personal, desperate.
Like someone trying very hard to prove they're not an insider. Less than twenty-four hours after our conversation about information security.
"Alex?" Grayson's voice seems far away. "You okay?"
"Fine." I shove my phone away, but the words keep echoing.
Every CEO just another wolf. Even ones who trust you. Even ones who love you.
"Okay, that's it." Connor steers me toward the mall's high-end bar. "We're doing this the old-fashioned way. With scotch."
"It's two PM."
"It's five o'clock in our stock options."
The nearby St. Cardigan bar is quiet, all dark wood and discrete service. Perfect for three tech billionaires having a crisis over Christmas shopping and corporate trust issues.
"Talk," Connor orders once we're settled with drinks that have more zeroes than they should. "What happened last night? And don't say nothing – you've been off since Mac left this morning."
I stare into my scotch, remembering how she'd tensed when I mentioned the blog's detailed numbers. How her kiss goodbye had tasted like guilt.
"Have you ever..." I start, then stop. "What if someone you trust completely is hiding something?"
"Ah." Grayson sits back. "The famous Drake trust issues emerge."
"I don't have?—"
"Please." Connor snorts. "You've had trust issues since Jessica Martin. Then your parents' divorce, then Drake Technologies' collapse. Now Mac's blog has you speed-dialing your emotional walls."
"This isn't about Jessica or my parents." I take a larger sip than strictly necessary. "This is about... information security. "
"Right." Connor's voice drips skepticism. "Because nothing says 'Christmas spirit' like corporate espionage concerns twelve hours after having your girlfriend over for dinner."
"The blog posts?—"
"Are changing the industry," Grayson cuts in. "Making it better. Like someone else I know used to talk about, back before he built walls thicker than his bank account."
I think about Mac's latest post. About the anger beneath the words, the desperate edge to her criticism. About how it went live just hours after our conversation about trust.
"What if change comes at too high a cost?"
"What if fear of being hurt makes you miss something amazing?" Connor counters. "Because from where I'm sitting, you've got bigger trust issues than my last software update."
My phone buzzes again – Emma, with PR's analysis of Mac's post. Words like "concerning" and "aggressive shift in tone" jump out.
"Buy her the emerald ring," Connor says quietly.
I look up sharply. "What?"
"The one you were staring at like it held all the answers. Buy it." He finishes his scotch. "Because either you trust her enough to risk everything, or you don't trust her at all. And that ring scared you more than any blog post."
"That's..." Surprisingly insightful for someone who once tried to code his way out of a breakup.
"He's right." Grayson signals for another round. "Though my AI could definitely help with the exact stone specifications?—"
"No dating app analysis!" Connor and I chorus.
But later, after we've finished shopping (and several more scotches), I find myself back at Cartier. The emerald ring sits in its case like a question.
Or maybe an answer I'm not ready to hear.
My phone buzzes with another news alert: Mac's post is trending. Words like "wolf" and "Versace" blur together, posted less than a day after she'd sat in my kitchen, avoiding questions about information sources.
I buy the ring anyway.
Because Connor's right – either I trust her enough to risk everything, or I don't trust her at all.
I just wish I knew which one was scarier.