CHAPTER ELEVEN     BLURRED LINES

          It was early evening when Sam stepped into the warm, bustling din of Il Nido, a quiet little bistro tucked between two brownstones in the West Village. The scent of fresh basil and garlic wafted through the space as laughter bounced off the brick walls and wine glasses clinked on marble tabletops. The city outside buzzed in the way only New York could, but here, it felt a world apart. Like a small, welcome bubble of familiarity.

          Rhiannon and Mitchel were already at the table in their usual corner booth, Rhiannon nursing an Aperol Spritz and Mitchel halfway through a glass of wine that Sam could already tell was too expensive for a casual Thursday.

          "Finally," Mitchel said dramatically, standing to air-kiss Sam on both cheeks. "The elusive Miss Alcott arrives. Have you been detained by secret government work again or just playing house with Mr. Castillo?"

          Sam rolled her eyes, setting her tote bag down with a heavy sigh. "Can we not?"

          But Rhiannon was already grinning like a fox with a secret. "Oh no, honey. You are not skating past this. Rhode Island? For three days?"

          "Two and a half," Sam muttered, grabbing a menu.

          "With your boss," Rhiannon added, swirling her drink like a courtroom prosecutor. "At his private mansion."

          Mitchel leaned in. "You do know this sounds rather suspicious, right? It feels like you are breaking the rules which is very unlikely."

          Sam sank a little into her seat and groaned. She wished that the ground would just swallow her whole at this point, "I'm tired."

          "You're dodging," Rhiannon sing-songed.

          "Because there's nothing to tell."

          Mitchel tilted his head. "Then tell us the nothing."

          Sam hesitated for a beat too long. And that was enough.

          "Oh my God," Rhiannon gasped, eyes wide. "Did you fuck him?!"

          "What?! No!"

          Rhiannon leaned back in her chair, one perfectly arched brow raised in open disbelief. "Are you sure?"

          Mitchel rolled his eyes. "Rhian, she would never. Sam would sooner jump off the Manhattan Bridge than risk her sense of professionalism."

          Sam gestured toward Mitchel. "Thank you.."

          "But it's Harry," Rhiannon said, undeterred. "The man has literally sent you Cartier. Hell, even Buccellati."

          Sam winced. "That was for the company gala."

          "That was a $12,000 bracelet, Sam."

          "Okay—"

          "And the necklace for the Hong Kong conference," Rhiannon added, holding up her fingers as if counting the receipts. "That wasn't a loan. You still have it. Don't you?"

          Sam opened her mouth, then closed it again.

          "And remember the stiletto disaster last time she went to fashion week with him?" Mitchel jumped in. "He sent a car, had two pairs of Louboutins waiting, and upgraded her hotel suite to the one with a marble bathtub and private terrace."

          "He's generous," Sam said, feeling her cheeks warm. "He does that with people."

           Mitchel squinted. "No, babe. Rich people don't even do that with their spouses."

          Rhiannon sipped her drink with dramatic pause. "Tell me again how many other assistants he's flown out to his secret coastal mansion?"

          Sam pressed her lips together. She hates it that Rhiannon would do all her can to squeeze out the details from her and to make it worse, she's quite an expert of it. Maybe being with them tonight is her worst decision.

          "Exactly," Rhiannon said, triumphant. "That place is his safe space. So, you're the only person outside of his family who's even been there. And you suggested the property in the first place, right?"

          "Yes," Sam said slowly, as if saying it out loud would shrink the implications. "But that's only because I manage all his estate scouting and logistics."

          "And who else does he cook for?" Rhiannon pressed. "I mean actually cook, not cater. You said he made seafood pasta from scratch. The Harry fucking Castillo."

          Sam groaned, dragging a hand over her face. "He said he took some world-class cooking classes in Italy and Thailand. I don't know. Maybe he was just being polite."

          "Sam," Mitchel said gently, leaning forward now. "Sweetheart. I know you. You can compartmentalize better than anyone I know. But don't gaslight yourself. You've worked with him for what—six years?"

          "Six," Sam nodded, voice quieter.

          "And in six years, has he ever treated you like just an assistant?"

          Sam didn't answer right away. Her fingers curled around the stem of her wine glass.

          "It's complicated," she said finally.

          "Why?" Rhiannon asked, suddenly softer. "Because you've been working for him so long, you're scared to question it? Or because you've already questioned it, and didn't like what the answer might be?"

          That one hit too close. "Stop psychoanalyzing me, for the love of god."

          "Babe, you're being indenial." Mitchel tells her.

          Sam blinked down at her wine. She wasn't drunk, but the edges of her clarity felt a little less sharp.

          "I've seen how lines blur," she murmured. "And how people lose things they worked hard for because they confuse kindness with something else. And I've spent years making sure I don't do that. I don't flirt. I don't misread signals. I don't let myself think beyond what's appropriate. Because at the end of the day, I'm still his assistant."

          Rhiannon frowned. "But are you?"

          Sam looked up. "I mean... is that all you are now?"

          The table fell into a brief, unexpected silence.

          Sam's heart gave a small stutter. She reached for her water glass just to feel like she was holding something steady.

          She couldn't deny that she'd felt something different in Rhode Island. Not just comfort or affection but the weight of being seen. Of course the main catalyst is Harry paying attention to the version of her that existed outside spreadsheets and calendars.

          But what did it mean? She can't tell anything anymore. Sam shook her head. "I don't know. I've worked for him too long to feel anything. Or maybe, I've worked for him too long to let myself admit I might."

          The words hung between them like steam rising off a dish too hot to touch. And in that moment, Sam couldn't tell if her heart was racing from fear or something far more terrifying.

          Rhiannon leaned forward, her brows knitting together as she pushed her now-empty cocktail glass aside.

          "So what about Vincent?"

          The question came gently without judgment but it landed with a weight that made Sam's spine go taut.

          Mitchel stirred his espresso and looked away, suddenly very interested in his demitasse. Rhiannon, however, held her gaze steady on Sam, who, after a beat, dropped her eyes to the rim of her wine glass.

          "What about him?" Sam said, almost too casually.

          Rhiannon tilted her head. "You've been dating him for what? Three months?"

          "Four," Sam corrected automatically. "He's nice."

          "Nice?" Mitchel muttered under his breath.

          "He is," Sam insisted, though even to her own ears it sounded weak. "He understands how busy I am. He doesn't complain when I cancel on him or reschedule our dinners. He sends coffee when I have back-to-back meetings. He respects my space."

          "He sounds like a calendar app," Mitchel quipped.

          Sam gave her a withering look, but Rhiannon's gaze didn't waver.

          "So what happened after Rhode Island?" she asked.

          Sam hesitated. Her fingers traced the condensation down the wine glass. "We went back to work."

          Mitchel raised a brow. "That's it?"

          "We went back to the usual like doing calls, meetings, deadlines. Deadlines that I had postponed, mind you. And Harry didn't say anything else. He didn't mention what happened on the yacht. Or the coral reef. Or the way he said I mattered. Not a word."

        Rhiannon looked confused. "But how did you two act around each other?"

       Sam exhaled slowly, sinking deeper into the booth.

      "It's strange. We're doing everything we normally do like emails, pitches, meetings with vendors but something's changed. The rhythm is off. The banter isn't the same. It's like we're playing the same song but in a different key, and neither of us wants to acknowledge it."

        She paused. "There's this heaviness to it. I speak to him with more distance now, strictly professional and surprisingly enough, he does the same. Even Rita noticed it."

        "Oh?" Mitchel perked up. "What did she say?"

         "She looked at me the other morning while I was briefing Harry in the car and said, 'Someone sounds like they swallowed a corporate handbook.' And the worst part?" Sam laughed, humorless. "She wasn't wrong. I sounded so formal. So flat. Like I was trying to erase every trace of who I was before Rhode Island."

          Rhiannon frowned. "And Harry?"

          "He doesn't push," Sam whispered. "But he knows, I can tell. Sometimes he looks at me like he's trying to figure out what I'm thinking, and I can't tell if I want to scream or..." She trailed off, then forced a breath. "I don't stay long in his penthouse anymore. I do what I need to do, then I leave."

          Mitchel leaned forward. "Because it's hard to be around him now?"

          "Because I don't know how to be around him," Sam said. Her voice cracked just slightly.

          She shook her head and stared down at her hands.

          "Vincent doesn't make me feel like this," she continued. "There's no tension. No confusion and tightrope of unspoken things that would stress me out. It's easy and predictable."

          Rhiannon's voice softened. "But do you feel anything?"

          Sam hesitated again.

          "I want to," she said. "I want to want him. He's kind and charming. He texts me in French and calls me ma chère. He never makes me feel like I have to apologize for being busy."

           "But?" Rhiannon prompted gently.

          "But when I talk with him," Sam whispered, "There's no spark."

          There it is. The truth that is already brewing inside her chest since she came back from Rhode Island. The confession wasn't even liberating for her, in fact, it made her even more afraid of whatever is happening between her and her boss. She leaned back in her seat, the weight of it pressing on her chest. Her mind flicked back to the car ride from the landing strip in Rhode Island to the mansion, the silence between her and Harry. That thick, electrified stillness that followed them even after they got back to the city. He didn't ask for an explanation and she didn't offer one.

          She hadn't let herself think about why his silence mattered so much. But now, in the amber-lit comfort of a booth with her two best friends and the city humming outside, it felt impossible not to. Sam stared down at the swirl of dark red in her wineglass, her fingers curled loosely around the delicate stem of glass. The candlelight on the table flickered, casting golden shadows across her face as she gave a small, almost imperceptible shrug.

          "I mean... whatever this is," she said, her voice quiet but clear, "it'll pass."

          Rhiannon tilted her head. "You think so?"

          Sam nodded, though the motion felt heavier than she expected. "It has to. It always does. We do have a way of falling back into place and I can think of countless scenarios that we have misunderstandings for the past six years. Eventually, once we're neck-deep in contracts and launch events and a dozen other things, this weirdness, this tension, it'll dissolve."

          She took a sip of wine, longer than before, and smiled like she was trying to convince herself of the very words she spoke.

          "I've been through enough work cycles with him to know the rhythm. It's just an offbeat moment like a skipped note in a song. It doesn't mean the whole piece is ruined."

          Mitchel looked at her over the rim of his glass, but said nothing.

          "I shouldn't be stressing over it," she added quickly, as if pushing the thought before either of them could interrupt. "I have a full calendar next week, a backlog of emails, and Vincent wants to meet for dinner when he gets back from Montreal. I don't have time to overthink a—" she paused "—a moment."

          Rhiannon's brows lifted, her lips parting slightly, but she still didn't speak.

          Sam looked at both of them, waiting for a reaction. Maybe an argument, a sarcastic quip or something but nothing came. There's silence on the table and two pairs of eyes watching her slowly drain the rest of her wine in one long, steady sip. The glass clicked softly when she placed it back down on the table. Her pulse was still a little too fast and her throat a little too dry. She glanced at her friends again at their worried, quiet faces and something inside her flinched, not because they were judging her. But because they weren't. They weren't saying a word and that silence said more than she was ready to hear. She leaned back in her seat once again, folded her arms across her chest, and let out a breath that trembled more than it should have.

          "It'll pass," she repeated, softer this time.

          But for the first time, she wasn't sure if she wanted it to.

          The week blurred into a string of checklists, vendor calls, and endless revisions. Sam's planner had started to look more like a battlefield than a schedule, there are ink smudges, last-minute additions, and too many flagged pages. Benjamin Castillo's wedding was in just a few days, and the air in the Castillo offices had become tighter with every passing hour. Everyone had started speaking in slightly hushed tones, like even their voices had to stay coordinated.

          That afternoon, Sam sat across a polished table in the Castillo conference room with Benjamin, Margarita, Anna and their the lead planner brought in after the venue debacle. Swatches of fabric, printed floorplans, and a rapidly annotated guest list were spread out between them like a mosaic of elegant chaos.

          Sam tapped at her tablet while listening to Anna and Benjamin discuss the final placement of the string quartet. She adjusted the stylus in her hand, already noting which vendors needed confirmation within the next hour. She was in the zone as she hoped to god that this damn event would finish so she can have a breather.

          Until Margarita casually asked, "Sam, do you have a plus one?"

          Her stylus froze mid-stroke. She blinked and looked up, brows furrowed. "I—sorry, what?"

         Margarita smiled as if she had merely asked about the weather. "For the wedding. Have you decided on your plus one?"

          Sam paused, visibly thrown off. "I haven't really thought about it," she admitted, straightening in her seat. "I've been kind of swamped."

          Benjamin gave a short laugh. "You? Swamped? I thought chaos was your default."

          Anna chuckled while cross-checking vendor names, and Margarita just leaned forward a little, that glint in her eye unmistakable now.

         "Well, you still have a few days," she said. "What about your dress? Found one already?"

          Sam tucked a strand of hair behind her ear and gave a sheepish shrug. "I was planning to check after my shift today. Or maybe dig through my closet. I've got one or two pieces that might still be salvageable."

         Margarita's smile sharpened. "And if you can't find a dress, I'm sure Harry wouldn't mind you picking one on the company card."

          Sam didn't respond immediately. She focused too hard on her tablet, typing something that didn't even make sense. She frowned as she reread what she just wrote, the youngest Castillo really loves teasing her and she hoped that she would just drop this conversation.

          It wasn't the word she meant. Not even close, Margarita watched her reaction like a hawk. "Harry doesn't have a date, you know."

          Sam stilled, the hum of conversation around her faded into a low buzz.

          She tried to say something but her throat caught around the first syllable like pesky fishbones stuck inside. She glanced up at Margarita, who was still looking at her like she'd just casually tipped over a secret.

          Before Sam could form a proper response, Margarita leaned back in her chair, smiling lazy but loaded.

          "I'm sure if you asked him to go with you, he'd say yes." Sam blinked twice.

          Benjamin was suddenly far too absorbed in a seating chart and Anna didn't seem to notice, flipping through vendor files as if the entire atmosphere hadn't shifted. Sam lowered her gaze back to her tablet, her fingers tightening just slightly on the stylus.

          Her heart tapped unevenly against her ribs.

          She wasn't sure what rattled her more, the suggestion or the part of her that didn't hate it.

          Sam had barely recovered from Margarita's loaded smile when she heard the soft but unmistakable sound of polished shoes against the marble floor. Her stomach dropped and she didn't need to look up to know who it was.

          Harry.

          He had just returned from a back-to-back meeting upstairs, sleeves rolled to his elbows, a folder tucked under one arm and a phone in the other. He was already speaking when he stepped into the room, but then his voice paused mid-sentence, "I heard my name," he said nonchalantly.

          Sam felt heat rise up her neck, and she forced herself to keep her expression neutral. She needs to remain calm but Margarita Castillo is now the bane of her existence. Professional is a skill she'd mastered over the years, but right now, it felt like someone had swapped her internal wiring with static.

          Margarita didn't miss a beat. "We were just talking about dates for the wedding."

          Harry raised an eyebrow as he set the folder down on the table. His gaze flicked across the room; Benjamin barely glancing up, Anna pretending to review centerpiece choices, and Sam who had suddenly found her tablet far more interesting than it ever had any right to be.

          He turned to his sister. "And?"

          Margarita leaned forward slightly, like she was about to share a delicious piece of gossip at a dinner party. "I said Sam doesn't have a date."

          At that, Sam looked up sharply, lips parting to interrupt, but Margarita continued without hesitation. "And you don't have a date either. So I said you should go together. I mean, you always bring Sam to charity auctions or fashion shows."

          A silence settled over the table; not heavy, but thick with anticipation. Harry's eyes moved to Sam, slowly and measuring how she would react. Not in that calculating, corporate way she was used to but in that maddeningly unreadable way that made her pulse skip a beat.

          He didn't look amused or annoyed. If anything, he looked rather surprised of what is happening. Sam scrambled internally to pull herself together. She straightened a little, cleared her throat, and forced a thin smile.

          "Rita was just teasing," she said lightly, even though her voice came out a bit too fast. "I'm sure you already have someone in mind."

          "I don't," Harry said simply. That one word made her freeze.

          He glanced back at Margarita. "But what do you mean by 'I'd say yes'?"

          Margarita gave him a little shrug, feigning innocence. "I just figured if Sam asked you, you'd go."

          Sam's fingers gripped the stylus a little too tight. "You're making it sound like I already did."

         "Well, did you?" Margarita asked, eyes twinkling.

          Sam gave a quiet laugh, feigning amusement, but her voice cracked just slightly. "It's not really something you just drop in the middle of a logistics meeting."

          Harry was still watching her, his expression hadn't shifted much but there was something softer now, something unreadable, caught in the small furrow of his brow. Like he was trying to piece something together. Like he wasn't sure if she was flustered because of Margarita or because of him. Sam hated that she didn't know either.

          She looked down at her tablet again, desperate to steer the attention elsewhere. "Anyway, we were reviewing the vendor flow for Friday's event. Anna needs your approval on the transportation for the immediate family."

        Harry didn't press on to the matter. He simply nodded, his voice even. "Right. Let's go through it."

          But as he took the seat across from her, Sam could still feel it.

          There was that undeniable silence beneath the words, his glance that lingered a second too long and the way his presence seemed to fill more space than it should have. And worst of all, the way her own heart responded, it wasn't out of panic or dread but with the quiet thrum of something she wasn't ready to name.

          The rest of the meeting moved on in an odd rhythm, the way things do when something unsaid lingers just beneath the surface. Sam kept her eyes on the documents, her stylus tapping gently against the glass screen, but she felt Harry's presence more acutely than usual. His glances were rare and brief but she felt them. And the weight of their exchange or lack thereof, hung between them like a curtain neither wanted to draw open.

          When the final details were settled and Anna collected the last of the contracts to forward to legal, Sam stood, ready to excuse herself and bury herself back into the security of her task list. But before she could make a clean exit, Anna's voice interrupted.

          "Harry wants a quick word before you go," she said gently, as if it were nothing.

          Sam blinked. "Oh, I already sent him the updated emails this morning. Everything's approved. He doesn't really need me."

          But Anna just gave her a small smile, one Sam recognized. The kind of smile that said don't try to wiggle out of this. She sighed quietly, nodding.

          Sam sighed heavily, "Alright."

          She followed the now-familiar path to Harry's office, trying not to overthink it. She wasn't being summoned about what Margarita suggested earlier. It was just work, maybe a check-in for his upcoming schedules. Why the hell is she overthinking this? She shouldn't be overthinking any of it? And yet, her pulse was louder than it should've been.

          Harry was already inside, standing near the window, his arms crossed and his expression unreadable. When she stepped in, he gestured to the seat across from his desk.

          "Close the door, please." That didn't help the nerves. Sam obeyed to his request, trying not to let her unease show, and took a seat across from him, smoothing the hem of her skirt unnecessarily. For a moment, Harry didn't speak. He just looked at her with that quiet, thoughtful intensity that always made her feel like he could see more than she ever wanted to reveal.

          Then finally, he said, "I just wanted to apologize."

          That caught her off guard. She blinked. "For...?"

          "If Margarita made you uncomfortable earlier."

          Sam gave a tight smile, waving a hand lightly. "Oh, that? Don't worry about it. Rita has always been like that to me. It's nothing."

           Harry tilted his head slightly, his gaze steady. "Still. I know how she can be."

          "It's fine, really," Sam repeated, trying to sound breezy, unaffected.

           But she could hear her voice faltering at the edges. She felt too stiff in her chair. And she knew that he could see right through her.

           He leaned against the edge of his desk, arms still crossed. "Are you alright?"

          Sam's breath caught. "What do you mean?"

          Harry didn't soften the question. "I just want to know if there's something bothering you."

          Sam felt her throat tighten. Her first instinct was to say no, to brush it off, to keep the line between them as straight and untangled as she could manage. Instead, she forced a crooked smile. "No. Nothing's bothering me. I think I'm just burned out. Too many spreadsheets since last Monday. Also, too little caffeine."

          Harry didn't look convinced, but he nodded. His eyes lingered for a beat longer than usual before he spoke. "You should take an early out today."

          Sam blinked. "Are you sure?"

          "I insist," he said. "You've earned it."

           She stood, collecting her tablet, grateful for the lifeline, even though everything inside her still felt off.

          She had just reached the door when his voice stopped her. "Sam."

          She turned around and saw him looking at her, almost losing her breath by the way he looked at her. Harry's tone was softer this time, careful. "Do you want me to be your plus one at Benjamin's wedding?"

          Her eyes widened, caught between surprise and something warmer she wasn't ready to define because deflection was her last defense, she tilted her head and gave him a teasing grin, "Do I even have a choice?"

          Harry's mouth twitched, just slightly. "Not really."

          "Then I guess I'll take you," she said, feigning a sigh. "But only if you behave."

          He nodded once, and even though the room felt heavy with everything unsaid, her heart still managed a quiet, unwelcome flutter.

          And as she stepped out into the hallway, alone again, Sam couldn't help but wonder, how did this all start feeling so dangerous and so impossible to walk away from?

anj speaks!

i would like to ask if you all want a prequel for harry and sam, basically what happens during six years working with harry and eventually forming their feelings for each other! i'm thinking on naming it as "when harry met sam" inspired to the title of the film, when harry met sally (1989) lmk your thoughts!