Faking It With The Boss's Son
Plot Summary
New office worker Tessa agrees to become an honorary big sister to her coworker Marlene's son, assuming he is a young child. When she meets Marlene's son, she discovers he is an adult doctor two years younger than her named Reid, who quickly starts teasing her with the playful nickname "Ma'am".
Marleen arranged for the two to spend time together, revealing she originally hoped Tessa would become her daughter-in-law after learning Reid hasn't dated anyone in years, setting up an unexpected romantic connection between the pair.
Search Tags
- Character-focused:
- Tessa, Reid, Tessa and Reid, Marlene and Reid
- Plot-focused:
- what happens to Tessa when she meets Marlene's son in Faking It With The Boss's Son, will Tessa date Reid in Faking It With The Boss's Son
Character Relationships
1. Tessa & Reid: Tessa is arranged to be Reid's honorary older sister by Reid's mother Marlene. The two are around the same age with Tessa slightly older, and Reid playfully teases Tessa with the nickname "Ma'am" after their first awkward meeting. There is clear romantic tension between them that Marlene actively encourages.
2. Marlene & Reid: Marlene is Reid's loving, meddling mother who wants Reid to start dating again after years of being single. She pushes the relationship between Reid and her new coworker Tessa, hoping Tessa will become her daughter-in-law.
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My coworker asked me to be a big sister to her son.
I said yes. Obviously. I figured the kid was, what, six? Seven? Missing a front tooth?
He's two years younger than me. He's a doctor. He's a full head taller than I am.
And right now he has me backed into my own couch, one arm braced on either side of my head, his mouth at my ear.
His voice comes out low. Rough. Almost amused.
"Ma'am?"
Chapter 1
The thing about agreeing to be someone's honorary big sister is that you really should ask how old the brother is.
I did not.
So when I clocked out that night and found a man waiting outside the building, I did what any functioning woman would do. Black jacket. Shoulders that took up the whole doorway. A jaw that made me lose my train of thought mid-step.
I looked. Then I looked again.
That was when my coworker waved at him. "Sweetheart! Over here!"
Sweetheart. Her son. The one I had signed up to be a big sister to.
I'm five-four on a good day. He cleared me by a head.
Someone bury me.
Let me back up.
I'd started at the new company a few weeks before, and somewhere between the first awkward lunch and the third, Marlene from two desks over decided we were destined. Not romantically. The other kind, where a woman twenty-some years older takes your wrist in the break room and informs you that you're family now and the matter is closed.
She called me her little sister. She kept my drawer stocked with snacks. And she talked about her son like a brochure: top school, a doctor, the whole package. I should be a big sister to him too, she said.
I'd pictured a child. I would like that noted for the record.
Back in the parking lot, the child in question was reaching out a hand. Not to me. To his mother, who beamed up at him like he'd personally installed the moon.
"This is Tessa." Marlene towed me forward by the wrist. "Reid, honey, I've got a feeling about you two"
"Mom." Low. Even. "I've told you. I'm not looking to date anyone."
"Who said date?" She swatted his arm. "She's family. She's older than you, and you'll show her some respect."
The whole lot went quiet.
He looked at me then. Actually looked. A slow drag from my face down and back up again, unhurried, like he had all the time in the world and had decided to spend it here.
Then he chose the single most dangerous word available to him and delivered it perfectly flat.
"...Ma'am?"
I had nothing. Not one word.
Bless her, Marlene took my silence for a yes and folded me bodily into the passenger seat of his car. "Drive her around, show her the good food, she's new in town." And then she was gone, and it was just me and the son.
He pulled into traffic. Caught my eye in the rearview, and the corners of his did that almost-smiling thing.
"Sure," he said softly, to no question at all.
Fifteen minutes later he parked, came around, and had my door open before I found the handle. He held it. Watched me climb out with the same not-quite-smile.
"After you, ma'am."
He'd decided. I could see it land. Ma'am was a permanent fixture now, and he was going to enjoy every single one of them.
The place had no sign and a line out the door. He waited until we were seated to say anything at all.
"It's good here." He didn't glance up from the menu. "Eat."
I nodded and murmured a thank-you to my water glass. Very smooth. Very big-sister of me.
Marlene, meanwhile, was a one-woman welcome parade. She poured my tea before I could reach the pot and launched into the full origin story of why her son now owed me the rank of elder.
Reason one was simple: she liked me. Liked me on sight, decided we were sisters, end of discussion. And a mother's sister outranks a son. That's the hierarchy.
Reason two, she had to lean in and drop her voice for.
Chapter 2
"Honestly?" Marlene squeezed my hand like we were trading state secrets. "I'd hoped you might be my daughter-in-law."
My brain tripped over daughter-in-law and went down hard.
"But." She sighed, long and tragic. "Reid doesn't date women. Hasn't in years. I've mostly made my peace."
Oh.
Oh.
Well, that solved the mystery. You don't get to look like that and stay single by accident. The math finally closed: I hadn't gained a devastating maybe-something. I'd gained a daughter. A tall, scowling, gorgeous daughter who would never once look my way.
Shame.
I lost my appetite somewhere around tragic and stared at a spread of food I no longer wanted.
"What are you thinking about, ma'am?"
A piece of chicken landed on my plate. I looked up. Reid was watching me, one brow raised, close enough that it was a problem.
Marlene was gone.
"Restroom," he said, before I could ask. Flat. Helpful.
"Oh."
The quiet stretched. I jabbed at it with small talk, because I am a coward.
"So. Where'd you go to school?"
"Med school."
"...Right." I sipped my tea. "Do you read?"
"I do."
A reader. Finally, something to work with. I sat up. "What kind?"
He leaned back, set one hand flat on the table, and took his time. Then, with a perfectly straight face:
"Older woman. Younger man."
Not a flicker on his mouth. But it was there, way back in his eyes, the laugh he wasn't letting out.
He was doing this on purpose.
He might as well have said your kind of book, ma'am.
I was still rummaging for a comeback when Marlene swept back in, and dinner became a party, because that was her gift. She could make a folding chair feel like a holiday.
Right up until she went to the restroom a second time and didn't come back.
She'd run into people she knew. A whole table of them, it turned out, short one player for cards and unwilling to take no.
She patted my hand on her way past. "Tessa, baby, the girls need me. Reid'll run you home after. He drives careful, I trust him."
And then, again, she was gone.
I swallowed and turned to the man across from me.
He had a toothpick between his teeth and the patient look of someone who'd been waiting all night for the table to clear. He raised a brow.
"Eat, ma'am."
I'd spent the whole evening certain I was babysitting a stiff, buttoned-up doctor.
Watching him now, the easy sprawl, the toothpick, the way the whole room seemed to angle itself toward him, I revised the file.
This was not a doctor.
This was the kind of man who ran things. And his mother had just left me alone with him.
Chapter 3
I glanced at the barely touched food and opted for a strategic retreat. "I'm full."
He tilted his head. "Full. Guess your appetite's smaller than it looks."
I nearly choked on air.
Smaller than it looks. As in, what, exactly, had it looked like?
He raised a hand for the check before I could mount a defense. I leaned in and added, "Could we get a couple of to-go boxes? Thanks."
He looked at me like I'd ordered a second dinner.
"It's a waste to leave it," I said quickly. "I'll pack it up for Marlene."
He didn't comment. Just tapped his card to the reader and helped me box the leftovers, one neat container at a time.
"Reid." His name came out stiff on the walk to the door. He could call me ma'am all night; I drew the line at calling a grown man "son."
He pushed the glass door open and stepped aside to let me through. I shrugged my jacket up around my shoulders. "Let's swap numbers. I'll Venmo you my half."
He looked down at me for a few seconds. Then he laughed.
"Ma'am. That's a pretty old-fashioned way to ask for my number."
Excuse me?
I glared at him. "Don't flatter yourself. I want to split the check. Because"
Because I pay my own way. Because I had a whole two years of seniority on this man and not one cent less of pride.
"Because I'm the adult here," I finished. "I cover my own meals."
That the adult was a grand total of two years older than him was beside the point.
He didn't look remotely wounded by adult. If anything, the corner of his mouth ticked up. He rattled off his number, then added, helpfully, "That's my cell."
I pulled up a new contact. His photo was the back of his own head. His name, just: Reid.
Mine, sitting there beside his, looked unhinged by comparison. A fat orange cat mid-yawn, under a handle that read itstessaaaa.
We got back in the car. I had my thumb hovering over the Venmo button when a hand came down flat over my screen.
Pale. Long fingers. Knuckles you could have sketched.
That was the first thing my brain reported, unasked. I looked up and caught his profile, and here is the thing about certain people: every time you look, you resent the universe a little more. No bad angle. Not one.
"Don't bother," he said. "Just buy me dinner next time, ma'am."
There was no graceful way to argue with that, so I nodded.
He drove me home. At my gate he turned, one wrist draped over the wheel. "Want me to walk you up?"
"No." I unclipped my belt and ran the script on autopilot. "Drive safe. Go slow."
"Sure."
I climbed out, and through the lowered window I watched him prop an elbow on the frame and light a cigarette.
It looked fine. It looked annoyingly fine.
I made myself stop looking, waved, and went inside.
Strange man. A doctor in a white coat with the manners of someone who had never once been told no. Younger than me, and somehow running every room he stood in. Gorgeous. And, per his mother, completely uninterested in women.
I slept well.
I slept well because I dreamed about him.
In the dream he had me backed into the couch, the two of us close in a way we had never been, and he leaned in and set his mouth against the edge of my ear, soft, and called me one thing.
"Ma'am."
I woke up.
What. Was that.
Chapter 4
The dream cut off there.
I woke against the headboard and sat with it a minute, which was a mistake, because the longer I sat the more my chest ached.
The tightness had been there for days. This morning it had teeth.
I did the responsible thing and looked it up online, then did the irresponsible thing and pressed around where it hurt, and somewhere between the two I'd convinced myself I could feel something. A knot. Something hard that had no business being there.
I am not a brave person. By the time I'd spiraled through three terminal diagnoses, I'd called in sick, flagged a cab, and pointed it at the nearest ER.
Weekday morning. The place was nearly empty. Two people ahead of me, a few minutes on a hallway chair, and then a speaker crackled out my name.
I went in clutching my paperwork and stopped short.
A male doctor. Of course. Head down, backlit, face in shadow.
Fine. Doctors are doctors. A body is a body. Very mature of me.
I sat, slid the paperwork across the desk, and started in. "Hi, so, my chest's been hurting for a couple days, and I"
He looked up.
A word my mother would not have approved of nearly made it out of me.
White coat. A pen turning idly between two fingers. That same not-quite-smile, aimed right at me. That ridiculous, unfair face.
"Ma'am?"
"R Reid?"
It came out in pieces. Shock does that.
He raised a brow and settled back, elbows on the desk, hands loosely laced, taking his time looking at me.
"Where does it hurt, ma'am? Given our relationship, I'll be thorough."
He was doing it on purpose. He was always doing it on purpose.
I sat in the patient's chair, unable to leave, unable to stay.
"Ma'am?" he prompted, once I'd stalled long enough. "There are other patients waiting."
Translation: move it along.
I repeated thorough to myself a few times like a hostage, then slid the paperwork back at him. "My chest. For a few days. I looked it up, and when I press on it I think I feel a lump."
He skimmed the page. Looked up. "On the table."
My face went hot and I opened my mouth to argue, but he was already nodding at the exam table by the door.
I went. I sat.
"Lie back."
"It's my chest that hurts, not my spine. Why am I lying down?"
His brow arched. "Are you the doctor, or am I?"
I lay down.
He crossed over and pressed two fingers exactly where I'd pointed. "Here?"
"Ow."
"Here?"
"Also ow."
Maybe it was nerves. Everywhere he touched, I yelped. His frown deepened, and so did my certainty that I was dying, and somewhere in there the embarrassment burned off and left plain fear in its place.
For the record, he was nothing but professional. Clinical, careful, not one inch of him out of line.
"You can sit up."
He went back to the desk, wrote something, tore off a slip. "Go get some imaging done."
I checked his face as I reached for it. No smile. Nothing at all.
My stomach dropped, and I took the slip and got out of there before he could put whatever it was into words.
Chapter 5
I came back with the report and a low, crawling dread. "Is it bad?"
Reid glanced at me and pushed his glasses up his nose.
That was when I noticed he wore glasses on the job. Wire frames, settled just so. The exact look of a man who is polite right up until the second he decides not to be.
"It's nothing," he said. "You probably just slept badly."
I blinked. "That's it?"
"What were you hoping for?"
I pressed my lips together. My voice dropped without my permission. "But this morning I really did feel a lump"
He looked at the screen and gave me the diagnosis in four flat words. "It's in your head."
Right.
Whatever. My heart finally climbed down off the ceiling. And, miracle of miracles, my chest didn't even hurt anymore.
I was working out whether to say something grateful on my way out when he spoke again.
"Ma'am. For what it's worth, you came to the wrong place for this."
I snatched the slip back. "ER. Chest pain. Seems right to me."
"Pain like yours, you'd normally get sent up to a specialist." He said it mildly, eyes on his screen.
"And you couldn't have led with that?"
He leaned back. When he looked at me, there was something almost like a smile in his eyes.
"Because the specialist on call today is also a man." A beat. "And it's minor. I can handle it myself. No reason to let another man put his hands on you."
No reason to let another man. His, apparently, were the exception.
I didn't ask. Obviously I didn't ask. I said a mangled goodbye and walked out with my whole face on fire.
Whether it was all in my head or whether his two-finger poking had worked some medical miracle, I couldn't tell you. The point is the chest pain packed up and left.
Since I'd already burned the sick day, I skipped the office entirely and called in reinforcements. Shopping. Facials. Maybe a club after.
Cleo picked up on the first ring. Cleo always picks up. My trust-fund best friend has never once turned down a plan in her life.
The club, though, she vetoed on sight. Her reason was simple and shameless: car show tonight, and the place would be crawling with gorgeous male models.
Which. Fair. Men. Models. I am only human.
So we spent the afternoon trying on new clothes and getting buffed to a shine, and then we walked into that car show glowing, ready to appreciate some scenery.
The first thing I spotted in the crowd was not a male model.
It was Reid.
What kind of cursed luck is this. I cannot go anywhere without tripping over this man.
I caught that face across the floor and lost my nerve on the spot. "Cleo." I tugged her wrist. "You know what, let's just"
She shoved my hand off without looking, eyes locked across the room, lit up like Christmas. "Hush. I just spotted treasure."
Naturally I assumed my little heiress had clocked a car. Half the floor was women's models, after all, which was the entire reason for the parade of long-limbed men.
I had, however, miscalculated.
Chapter 6
Cleo's treasure was not a car. It was not one of the male models either.
It was Reid.
I trailed after her and watched, helpless, as she crossed the floor to where he stood studying some sedan, arranged herself against the driver's door in that scrap of a dress, and tipped her head.
"Hey, handsome. Buying?"
She looked like she belonged at the show, smiling up at him, a professional. Cleo is gorgeous. Pale, lethal, raised on money, with the easy arrogance of a girl who has never once had to ask twice. The kind of pretty that does not miss.
It missed.
Reid gave her one glance. "Just looking." Flat. Cold. He turned back to the car, then moved to go, and walked straight into me.
He stopped. Something thawed at the back of his eyes.
"Small world, ma'am."
I was still assembling a polite response when his mouth tipped and he slid the knife in.
"Chest still bothering you?"
The chest was fine. The head had developed a problem.
I laughed it off and made a point of sounding professional. "All better. Thank you, Dr. Reid."
Cleo arrived at my elbow, hooked her arm through mine, and looked Reid up and down with zero shame. "Tessa. This gorgeous man is a doctor?"
I clicked my tongue. One look at her face and I knew: Reid had been filed under prey.
And something in me, for no reason I cared to examine, did not like that.
An elder's protectiveness, surely. A duty of care. I simply couldn't stand by and watch my own family get devoured by a little vixen like Cleo.
Although, with a face like his, the question of who would devour whom stayed wide open.
Reid finally turned and gave Cleo his real attention. She seized it. "Cleo. Tessa's best friend."
He nodded. Then he introduced himself, and I died on the spot.
"Reid," he said. His eyes cut to me, dead serious. "Tessa's family. I'm supposed to show her respect."
He said it. Out loud. Like it cost him nothing.
Cleo's face did something I had genuinely never seen it do. Her eyes went huge. She turned, planted both manicured hands on my shoulder, and shoved.
"Tessa. TESSA. When did you get your hands on a snack like this?"
I said nothing. There was no version of the explanation that fit in two sentences.
She wasn't wrong, though. Snack was accurate. Reid had worn a gray trench coat tonight, all long lines and shoulders, the kind of man clothes get designed on. From every angle, certified leading-man material.
While I was busy cataloguing Reid, Cleo was quietly cataloguing me.
I'd braced for her to make her move. Instead she did the opposite. A quick goodbye, and then she had me by the wrist and we were leaving.
No more car show. No more models. Cleo towed me straight out the door and pointed us at a bar.
I got in her car, still completely lost.
Chapter 7
"No more wild models for you?"
Cleo laughed. "They're legitimate male models, thank you very much." She flicked a glance at me. "I'm taking you out. And while we're at it, I'm going to teach you how to land him."
"Land who?"
Red light. She draped one hand over the wheel, turned, and winked, slow and loaded. "Your little family doctor. Obviously."
She put a spin on family that sent heat straight up my neck. "Who said I want to land anyone?"
Cleo has fox eyes, all the more dangerous under a good smoky liner. When she narrows them she looks like she's seen through every soul in the room. She narrowed them at me now.
"The way you were looking at him? You were one blink from peeling that trench coat off him in front of the cameras."
Me:
Was it that obvious?
I went quiet, which was its own answer, and offered up my last weak defense. "His mom said he doesn't date women."
I expected Cleo to mourn the waste alongside me. Instead she snorted.
"Relax. The way that man looks at you, there is absolutely a chance."
The light went green. She pulled away and added, almost an afterthought, "'Doesn't date women' is just what you tell your family so they'll leave you alone. Believe me."
From anyone else I'd have argued. But Cleo would know.
Her family had been after her for years to marry up, specifically to the son of some business partner. Cleo dodged and dodged, and when they finally backed her into a corner, she told them the one thing guaranteed to end the conversation.
She told them she was in love with me.
These days everyone in Cleo's house is fully briefed. Her parents. Her grandmother. The dog. All of them know that Cleo is hopelessly, tragically in love with her best friend.
So when she says a man might be lying to his family, she's speaking from experience.
Every light was green. We were at our usual bar in no time.
Park, walk in. Cleo had them bring out the bottle she kept on reserve and ordered enough snacks and liquor to suggest she fully intended to put me under the table.
She didn't get the chance to start pouring.
She stepped away to the restroom, and in the ninety seconds she was gone, I ran into a ghost.
My ex. Jesse.
Just going by the names, you'd assume we were made for each other. Tessa and Jesse. Adorable.
In reality, the man was a walking dumpster fire.
Two years in college. I gave him everything I had, and he repaid it by cheating on a scale I still can't fully picture. I could have run out for coffee and passed three girls he'd slept with on the way.
It ended when someone dumped a folder into the campus group chat. Screenshots, dozens of them. Jesse running half the women on campus at once, full conversations, three different dating apps. His name was mud overnight. Mine got dragged right along with it. Every cute couples post I'd ever made turned into a punchline.
Cleo handled the breakup the way Cleo handles everything. She showed up with two of her father's security guys, let them help Jesse rethink his choices, then dropped a stack of cash on him like a tip and walked me out under her arm.
Cleo has always been the fierce one. Years of friendship, and when I really sit with it, it was always her standing between me and the worst of it.
By the time I surfaced from all of it, he was already there. Close enough to touch. Smiling at me like the last two years had happened to somebody else.
Chapter 8
He dropped into the seat beside me, a drink in one hand and a girl with a spectacular figure on his other side.
"Well. If it isn't my ex."
The face hadn't changed much. It just looked a little more worn around the edges. Used up.
My stomach turned. "Don't call me your ex. It's disgusting."
I let the disgust sharpen. "And technically? I'm one ex on a very long list. Don't make it sound exclusive."
Jesse took a sip and leaned in to murmur against my ear like it was charming. "No, you definitely count as the ex." He laughed and tipped his head at the girl beside him. "The rest are just hookups."
Repulsive. Genuinely.
I leaned back and put real distance between us, then glanced at the girl. She was scrolling her phone, supremely unbothered by whatever Jesse thought he was doing. I caught her screen on the way past. A tidy column of incoming payments. She was doing great, actually.
Jesse followed my eyes, then looked back at me and smiled. "Told you. Just a hookup."
I was done with the whole pointless tug-of-war. I slid one seat over. "Say what you came to say or get lost."
It didn't faze him. Shameless to the bitter end, he laughed low, leaned in again, even reached for my hand.
I pulled it back. He grabbed air.
"Tessa. Real talk. I've had my fun, I'm tired of running around. Let's get back together."
I stared at him, genuinely unable to process the words.
Was he serious? How did a sentence like that survive the trip out of a human mouth?
But Jesse hadn't clocked my expression at all. He just kept going. "These last couple years, I couldn't stop thinking about you. All those girls, and you're still the one who mattered."
I drank alone and refused him a second glance.
Did he honestly think this was romantic?
He didn't get the chance to find out, because Cleo came back.
She didn't ask a single question. She upended a full glass of red over Jesse's head.
I turned and looked, briefly mourning the wine.
Cleo planted herself in front of me, square between us. "Jesse. You came back to bother her again? Guess I didn't make my point last time."
Jesse wiped his face, expression curdling. "Cleo. Don't think I won't hit a woman."
Cleo smiled, slow and contemptuous. "And don't think I'm bluffing. You lay one finger on either of us tonight, and by tomorrow my lawyers own your name, your job, and the lease on whatever hole you live in. I know exactly where to find you. Try me."
A couple of the closest tables had gone quiet, eyes politely elsewhere, ears wide open.
The standoff held a long moment. Jesse folded first.
He collected his girl and left, muttering "psycho" the whole way out.
The encounter left me wrecked, and the old memories came up with it, the way they always do.
Jesse was trash. I'd known that for years, and I'd told myself, just as many years ago, that I was over it.
Turns out you can be sure a wound has closed right up until someone strolls past and leans on it.
Two years. Seven hundred-some days. I gave every one of them in good faith.
Which was, in the end, the whole problem.
Chapter 9
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