Texting My Billionaire Boss

Texting My Billionaire Boss

Plot Summary

When office assistant Lila accidentally sends her intimidating billionaire boss Nathaniel Wolfe a link to Chicago's "Most Delicious" list, where he's ranked as the city's hottest eye candy instead of a restaurant, a flirty text exchange quickly leads to an unexpected invitation for a meal.

The awkward misunderstanding turns into tense romantic tension when Lila follows up the next day in Nathaniel's office, leaving both to navigate their hidden attraction and unexpected connection.

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  • Character-focused:
  • Nathaniel Wolfe
  • Nathaniel Wolfe and Lila
  • Plot-focused:
  • what happens to Lila in Texting My Billionaire Boss
  • accidental text to billionaire boss romance

Character Relationships

Nathaniel Wolfe & Lila: Nathaniel is Lila's demanding, notoriously cold billionaire boss, and Lila is his overworked executive assistant. A mis-sent text accidentally reveals Lila's private thought that Nathaniel is the most attractive man in Chicago, sparking a flirty exchange that forces both to confront their unspoken mutual attraction beyond their professional dynamic.

Lila & Her Bestie: Lila's bestie is the one who originally sent her the link to the "Chicago's Most Delicious" list, setting off the entire accidental encounter that changes Lila's relationship with her boss.

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Number one on Chicago's Most Delicious wasn't a restaurant.

It was my boss.

Nathaniel Wolfe. Glacial, terrifying, rumored to run on liquid nitrogen instead of blood. Somehow he'd topped a list of the most edible eye candy in the city.

And I'd just fat-fingered the whole thing straight to him.

Cold sweat, all the way down my spine. Then the phone lit up.

Him: [Want a taste?]

I had no idea what I'd walked into. I fired back in two seconds flat.

Me: [Can I?]

Chapter 1

The link had been sitting in my messages for a solid twenty minutes before I flicked it at my boss without even looking up.

Bestie had dropped it on me mid-match.

Bestie: [CHICAGO'S MOST DELICIOUS JUST DROPPED. you're welcome]

I'd swiped it away like the responsible professional I am and gone right back to carrying my team.

Then his name lit the top of my screen.

Snack (42-30-38): [Anything good to eat nearby? Send recs.]

Capitalism. Beautiful, bloodsucking capitalism.

I babysit this man's overtime until my vision blurs, and the second I clock out he's still in my phone like a subscription I never signed up for. I signed a contract. Not a bill of sale. There are three hundred people in that building, and somehow every single errand has my name on it.

So I made him wait. On principle. A workhorse can have a temper too.

I finished my game. Started another. Won that one, thanks for asking. Then I forwarded him the bestie's link, because it literally had eat in the title and that technically counted as a recommendation, and dove back in for round three.

When I finally came up for air, he'd written back.

Snack (42-30-38): [?

[You

[Want a taste?]

Well, well. Look who found his conscience. Something nice lands in his life and he thinks of little old me. Never let a freebie walk on by.

I sent him the drooling sticker.

Me: [Can I?]

The bubble popped up at the bottom of the screen. typing

Then nothing.

typing

Nothing again.

I flopped back and chucked the phone onto the pillow. Was he seriously getting cold feet? No wonder the whole message crawled out in three sad little pieces with ten-minute gaps between them. All that agonizing.

Over dinner.

Breathe, my guy. It's just food.

Chapter 2

Next morning I slipped into his office.

He'd just walked in, jacket halfway off, back to me. The white shirt pulled tight across his shoulders, sleeves straining over his arms, down to a lean waist, and lower

"Ahem."

I snapped to. Nathaniel Wolfe was watching me, something dark and unreadable in his eyes.

Right. The man docks your bonus for blinking wrong. I shoved the folder at him. "Mr. Wolfe. Last night's proposal."

He pulled his tie loose and dropped it over the back of the chair like it had personally wronged him. "Mm. Leave it."

He sat. I stayed put. He looked up. "Something else?"

The shadows under his eyes had shadows of their own. "Rough night?"

"Couldn't sleep."

Huh. Not because of me. Obviously not. Definitely not.

I pushed my luck. "So. That thing from last night. We still on?"

He went still. Something crossed his face that I could only file under uncomfortable.

Come on. It's a meal. I'm not asking for a kidney. Then again, the man's a certified icebox, a local legend of one, and getting spotted at dinner with some woman, alone, would do real numbers on the reputation. I'm his secretary on top of it. Maybe last night was just him being polite and I was too slow to catch it.

"You really think that," he said, low. Like the words cost him something.

I switched on my best good-girl smile. "Heh. I've been eating clean way too long. Just wanted something good, you know?"

Three weeks of sad desk salad. My face was going the same shade as the kale. A girl needs red meat.

He blinked. His ears went red. Slowly, from the tips down. "Let me think about it."

Unbelievable. Still dangling the carrot. And he had the gall to sit there wearing the face of the wronged party.

I roasted him top to bottom, silently, in the safety of my own skull, and out loud I laughed it off. "Kidding, Mr. Wolfe. You're swamped. I'd never waste your time. I'll just ask someone else."

Someone else.

The color drained out of his face.

His jaw locked. His brows drew tight. He stared at me like I'd pulled a pin on something live.

He fought it. I watched him fight it. Then, like a man signing his name to a deal he already regretted: "Fine. I'll do it. Don't go bothering anyone else."

I gave him the blankest look in my collection.

Why did that land like a shotgun wedding?

He cleared his throat. "It's my first with you. Anything I should know? So I can prepare."

Aw. Asking about my dietary restrictions. Thoughtful, in his stiff little way. And the whole floor knows I like it hot. I swallowed, practically tasting it already. "I run heavy, honestly. The more it burns, the better."

Nathaniel Wolfe went the color of a stoplight.

"Get out."

Chapter 3

Back at my desk, water cup in hand, my phone buzzed.

Bestie: [WELL?? did you pick one??]

Me: [already sorted it with Nathaniel Wolfe. he's handling it.]

Bestie: [YOU BRAT. FOR REAL??

[Josie Wells, how are you this feral. teach me your ways]

Me: [the man's been working me to the bone for years. i'm allowed one little treat.]

Bestie: [ICON. we've all been quietly thirsting over that man for YEARS and you just reached out and grabbed him. legend behavior]

I was halfway through a suitably withering reply about her thirst levels when a coworker slid up to my desk like she was defusing a bomb.

"Jo. Did something huge just go down?"

I blinked at her. "No? Where are you even getting your gossip?"

She dropped her voice. "Mr. Wolfe. The entire morning meeting, just staring into space. Scared us half to death. Is the company going under? Jo, if you know something, you have to warn me first"

I remembered exactly how thunderously red he'd gone when I left. My smile came out crooked.

God. I'd completely forgotten the man has the blandest palate in the building. I told him the more it burns the better, and now he's sitting in a conference room quietly unraveling over it.

"He probably just pulled another all-nighter," I said. "You saw the eye bags. Honestly, with a workaholic like that, worry about yourself keeling over at your own desk first."

I sent her off and snuck a look at Nathaniel, freshly out of the meeting room.

Brow furrowed. Jaw tight. Something lost and helpless sitting on a face that never lost anything.

I hadn't seen that look on him in years.

This was a man who'd built an entire career out of never once flinching. One time, some idiot fat-thumbed his shirtless gym selfie into the company-wide chat, and Nathaniel Wolfe just turned to me, standing right there, and calmly asked what I thought of it.

What was I supposed to say?

I praised the goods. Warmly. Every word true, and God help me, effortless.

That was the day half the women on the floor, me included, quietly tacked a little string of numbers onto his contact name.

Snack (42-30-38).

Look. A girl needs something to get her through the nine-to-five.

Chapter 4

Come Saturday, bestie summoned me to her place. Very important, she said. Life-or-death, she said.

I didn't see how one dinner warranted a war council, but I grabbed a bike share and pedaled over anyway. Between the job and the overtime, this was the closest thing to exercise I got. Might as well sweat off the sad desk salad.

His text came while I was mid-pedal.

Snack (42-30-38): [Strawberry or chocolate. Which flavor do you like?]

Ooh. Already picking dessert. My stomach did a happy little flip.

Steering one-handed, wobbling all over the lane, I thumbed back:

Me: [STRAWBERRY. NON-NEGOTIABLE.]

I didn't get to hit send.

A streak of orange shot out of the bushes. A kitten, tiny and suicidal. My body swerved before my brain caught up.

The bike lurched. The front wheel went one way. I went the other.

The pavement came up fast.

Pain drove straight through my ankle, white and total. I sat there stunned before the world swam back into focus.

I looked down. In the time it took to blink, the scrape had ballooned, fat and shiny.

I tried to shift my weight up. The second I leaned on it, the pain shot clean to my scalp.

I hissed, hopped one-legged to the curb, and called a car to the hospital.

The doctor, glasses shoved down his nose, gave my scan a bored glance, decided I wasn't worth his time, and waved over the intern beside him.

The kid clearly hadn't done this often. His hands actually trembled as he cradled my ankle and dabbed on the ointment. Green, anxious, painfully careful. He looked exactly the way I had, fresh out of school.

Back then I was nobody. The other new hires were Ivy League, or somebody's kid. I was just a regular person, walking on eggshells all day, terrified of one wrong step. They all found the right coattails to ride. I fit nowhere.

Except with him.

Nathaniel Wolfe never once looked through me for being an intern, never once pitied me for having no name behind me. He saw the work, or he saw nothing. Do it well and even a nobody got pulled up. Do it badly and he'd tear a strip off you, nobody or VP, made no difference.

That fairness was the kindest thing anyone had ever handed me.

There'd been nights before him when I sat shaking in the dark, the phone screen gone black in my hand, the day's insults still lodged somewhere under my ribs.

He was the one who taught me the trick of it. Get strong enough, and every blade thrown at you just glances off the shield. He handed me that shield. He handed me trust.

And now I could pass a little of it on.

The ointment stung. The doctor's palm worked it in, too gentle, then too hard, and I flinched.

My phone rang.

Right. I still hadn't answered him, and the man loathed nothing on earth more than being kept waiting.

I picked up. His voice came through startlingly gentle.

"Did you get my message?"

"Ssss. Yeah. Saw it."

"Then why didn't you answer? You don't like either one? Josie" A pause. "Don't tell me you run heavy here too. Fine. Tell me what flavor you want. I'll go find it."

I had no brain left to decode him, because right then the intern pressed down hard on my ankle and the pain went white behind my eyes.

"Ah, it hurts! Go easy, easier"

Not another word would form. I hung up on him and rode out the wave, breathing through my teeth.

When it finally ebbed, I realized I had the poor kid's hand locked in a death grip. Nail marks sunk deep into the back of it, the skin already blooming purple.

I let go fast. Before I could even apologize, his voice cracked out first.

"I'm sorry I'm so sorry. I'll go get the attending"

The boy shot to his feet, red to the ears, wearing the face of someone who'd just bombed an exam.

He was halfway to bolting when I caught his sleeve. "Go now and all you'll get is chewed out. Won't fix a thing."

He hesitated. "But your ankle"

I tugged him back into the chair. "It's fine. Keep going. I trust you."

He looked at me. Looked at the ankle. And under whatever he found in my face, he picked the ointment back up and started again, careful as anything.

"You're really not mad?" he asked. "Most people, as bad as I am at this, they'd have raised hell already."

I could have been. I'd met bosses who made an art of it, who fired words like arrows and left me bleeding quietly at two in the morning.

But I just smiled. "It's a bruise, not an amputation. You get another shot. Everybody's got more in them than one bad day shows. You included. Who knows, maybe someday you're the one who saves a whole roomful of people. I'd hate to cost the world a decent doctor over one sprained ankle."

He stared like I'd handed him something breakable.

"So," I added. "Don't you dare make a liar out of me."

Chapter 5

I called in three sick days with HR and eased into the sweet, horizontal life.

Slept until my body decided to wake up. Rolled over, thumbed my phone open.

The office group chat had been feral since dawn.

[why is Wolfe losing it AGAIN??]

[you did not see his face. dead of summer and I broke into a cold sweat]

[HELP our team lead turned in a deck, got verbally disassembled, and is currently crying to his wife in the third-floor bathroom]

[do NOT scare me I have a doc for him to sign in ten minutes. do I make it out alive]

[okay. rumor. RUMOR. Wolfe might, maybe, possibly have gotten his heart broken]

[WHAT. WHEN did that man date anyone]

[impossible. I have never once seen a woman within ten feet of him]

[sorry, and who are YOU]

I scrolled through it half-asleep. That was a genuinely alarming amount of information for this hour.

So that was why he wouldn't pick up when I called him back last night.

Some absolute legend out there had landed Nathaniel Wolfe, dated him, and dumped him. A hero. An icon. I hoped she was thriving.

Then I remembered I'd hung up on him mid-sentence, and a small guilty thing turned over in my chest.

I opened his chat.

Me: [Mr. Wolfe, something came up last night, I swear I didn't mean to hang up on you. Um is it too late to switch to strawberry?]

I'd barely set the phone down when he called. Didn't text. Called.

"Josie Wells." Every syllable came out chipped from ice. "I don't know how other people operate. I have never been the casual type. I have no right to interfere in an employee's personal life. But at the absolute minimum, it does not touch your work."

How does a mouth that runs at ninety-eight degrees turn out sentences that cold? I was on sick leave.

"I'm really sorry, Mr. Wolfe. I genuinely wasn't feeling well. That's the whole reason I took the days off."

"Is it that serious? You need three of them?"

Wasn't the reason right there on the form?

"Uh not that serious, honestly. Just a little swollen. Kind of hard to walk on"

"Stop." The word cracked out. "What do you take me for? Is this part of the little game you two are running?"

Game?

"Last night." His voice dropped, low and dangerous. "You picked up my call on purpose. While you were with him."

"What? There's no game. You're the one who said I always have to answer your calls."

"Then answer me this." Quieter. Worse. "Did I, or did I not, tell you not to go looking for anyone else. I already started getting ready. Two days. You couldn't wait two days. Or did you change your mind that fast?"

I held the phone away from my ear and stared at it.

"You chose me first," he said. "You don't get to walk it back. You're going to look me in the eye and explain yourself."

He hung up before I could get a single word in edgewise.

I sat there a long moment, phone dead in my hand.

I had no idea what he was talking about. But somehow, inexplicably, I felt like I'd just been cast as his cheating ex-girlfriend.

Does heartbreak scramble a man's brain this badly? Maybe he was looking at every face now and seeing the woman who walked out on him.

Absolute lunatic.

I chucked the phone across the couch.

Chapter 6

The doorbell rang while I was melted into the couch, scrolling.

I got up, caught sight of my pajamas, and seriously considered pretending nobody was home.

The bell kept going, relentless, like it had a personal grudge. I gave up, dug a pair of loose lounge pants out of the closet, yanked them on, and opened the door.

Two men stood on my doorstep, one on each side like a matched set of stone guardians, both wearing thunderclouds for faces. I actually flinched.

I skipped clean over the storm cloud that was Nathaniel Wolfe and looked at the unexpected guest on the right.

"Dr. Palmer? What are you doing here?"

The kid scratched the back of his head, drowning in apology. "Ma'am. I came to make it right. I hurt you last night because I wasn't good enough. I went home and practiced all night. I was hoping you'd give me one more chance to make it up to you."

He really didn't have to. We'd swapped numbers last night and he'd already apologized roughly nine times.

I was drawing breath to gently decline when Nathaniel Wolfe cut in, jaw clenched, every word ground out through his teeth.

"So when I called you last night. This is the loser you were with."

I didn't expect it to come out that ugly. It froze me for a couple of seconds. The air in the hallway turned solid.

I shot a panicked look at the kid. He wilted, visibly.

"I'm sorry, ma'am. It's all my fault, putting you through that." His voice shrank. "But I'm still young. I'll get better, I swear it. You said you'd believe in me, remember?"

Something in his careful, hopeful face got me. I went soft and nodded.

"Is this gentleman with you too, ma'am? Your uncle?"

Nathaniel looked like he'd been hit by lightning. He rounded on the kid, closing in, vicious, one wrong breath from throwing a punch.

The whole thing was two seconds from detonating. I threw myself between them. "Whoa okay, Mr. Wolfe! If there's nothing urgent, can this maybe wait until I'm back at the office?"

He stalled. Then his face settled into something cold and almost amused, the way a man smiles when he's too furious to actually laugh. "Josie Wells. The things I let myself sink to."

He turned on his heel and left. No hesitation. I had zero idea what I'd done to offend His Majesty this time, and I was still sighing about it in my head when he stopped. Turned around. Came back.

Bracing for whatever fresh horror was about to leave his mouth, I got there first. "What now?"

He looked at me through narrowed eyes.

"Just curious," he said. "Is this the type you women go for? The soft little pushover?" A beat. "Maybe I'll take some notes. You never know. Might come in handy one day."

Then he stepped past the kid, past me, and walked into my apartment like he owned the place.

Chapter 7

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