I stared at the glowing screen of my phone in the dead silence of my apartment, the blue light harsh against my exhausted eyes. It was past 2:00 AM, and a trending thread on Reddit’s r/TrueOffMyChest had suddenly snagged my attention. The original poster was claiming, with absolute, agonizing sincerity, that he had fallen hopelessly in love with five different women. All in the exact same day. He went into excruciating detail about the objects of his newfound affection: the young barista at the local boba shop, the DoorDash girl, his morning Uber driver, a quirky TikTok streamer, and, finally, his newly hired executive secretary. The comment section was a bloodbath of cynical internet humor. “Bro, loving one person in this economy is exhausting enough. You’re trying to roster five?” one top comment read. “This is honestly terrifying. It’s giving severe attachment issues,” another user chimed in. “You order a burrito and fall in love with the delivery girl? You get in an Uber and want to marry the driver? Seek therapy.” But as I scrolled through the digital roasting, a quiet, hysterical realization bloomed in my chest. I knew a secret none of these keyboard warriors did. Those five distinct women? They were all me. Because in order to survive in this city and keep my bank account out of the red, I was currently juggling five different jobs. And the tragically earnest poster getting crucified in the comments? That had to be my boss. The billionaire CEO who suffered from a documented, severe case of prosopagnosia—face blindness. 1 I had just kicked off my shoes after finishing my late-night side hustle when the post popped up on my feed. [Title: I think I’ve fallen in love with five women at the same time. What do I do?] Normally, I scrolled past relationship drama. I didn't have the luxury of time for romance; time was money. But as I went to close the app, the OP’s avatar caught my eye. It was a very specific, pretentious geometric logo. Wait. Is that Payne? My boss, Payne Sinclair? I clicked back into the thread, my fatigue momentarily vanishing. His narrative style was… uniquely unhinged. He explained that within a single twenty-four-hour window, he had been utterly captivated by a boba barista, a DoorDash rider, an Uber driver, a TikToker, and his new secretary. [This morning, both my Lamborghini and my Porsche refused to start. I had to resort to an Uber. The driver was this woman with a fiercely focused energy. But what really sealed the deal was the graceful, poetic way she rolled down her window and absolutely destroyed the lineage of a guy who tried to cut us off. It was beautiful.] The comments were relentless. “Which Wattpad billionaire romance did this guy escape from? ‘My Porsche wouldn’t start’? Bro, where’s the Rolls-Royce?” “The reason you fell for her is wild. She cussed out a dude in traffic and that did it for you?” Payne had actually replied to that one: [The Rolls-Royce is in the shop for detailing. And she didn't just cuss him out. I told her I was running late for a crucial board meeting, and she defied the laws of physics to get me there on time. She was protecting my schedule. She cares about me.] I sat on my lumpy mattress, staring at the ceiling in stunned silence. This morning, I had been doing my usual 5:00 AM Uber shifts. By some cruel twist of algorithmic fate, I had picked up my own boss. His gated community had a ridiculous speed limit, and just getting out of the neighborhood took ten minutes. He had a meeting at ten. I had to clock in at the office by nine-thirty. I was driving like a stunt double in a Fast & Furious movie. If anyone tried to merge into my lane, I verbally dismantled them. I got us both to the high-rise with two minutes to spare. That was how Payne Sinclair fell in love with me? Before I could even process the absurdity, I refreshed the page. He had updated the post. [Because I was so distracted by the memory of the Uber driver, I couldn't stomach the thought of going out for a proper lunch. I just ordered delivery. When the DoorDash girl arrived at my corporate lobby, some creep was harassing a woman on the sidewalk. My delivery driver took off her helmet and launched it in a perfect, parabolic arc, nailing the creep right in the back of the head. It was so badass. I am obsessed. The best part? She was holding my Thai food in her other hand, and she didn’t spill a single drop.] The comment section was losing its mind. “‘Couldn't stomach a proper lunch so I ordered delivery.’ Ah yes, the male capacity for making excuses is truly boundless.” “So you fell in love again? What happened to the Uber driver? Are we over her already?” Payne replied immediately: [I still love the Uber driver very much. We are currently at two women.] I put the phone down, grabbed a towel, and went to take a shower. Mid-shampoo, my phone buzzed on the sink. It was the manager of the boba shop. "Jill, you only worked a two-hour shift today. Do you even want your paycheck this week?" I didn't even bother rinsing the suds out of my hair before going on the defensive. "I did four hours' worth of prep in those two hours, and I didn't even charge you overtime. Plus, some guy practically choked to death in your lobby today and I gave him the Heimlich. I saved you a massive lawsuit. You're welcome." The manager paused. "Fair point. See you tomorrow. Don't be late." He hung up. I wrapped a towel around myself, picked up my phone, and saw another update on Reddit. [After work, I needed something sweet to calm my nerves, so I went to a boba shop. The barista there… her eyes looked so familiar. It felt like I had known her in a past life. I was staring at her, trying to figure it out, and I got so flustered that I inhaled a tapioca pearl right into my windpipe. I nearly died. But she vaulted over the counter and saved my life. I think I love her too.] [This feeling of having my heart pulled in so many directions is agony. A friend told me to just doomscroll on TikTok to distract myself. I did. I found this streamer. She is incredible. She can balance an entire dining chair on her chin while reciting the alphabet backward.] I stepped out of the bathroom and nearly tripped over the ring light I used for my streams. The comment section had officially turned into a circus. “This is unhinged. You’re just falling for every woman you make eye contact with.” “If you’re such a rich CEO, act like it. Call your secretary right now and demand background checks on all of them. Assert dominance.” Payne actually responded to that one too. [I absolutely cannot do that. Because I think I’m in love with my secretary, too. She is fiercely competent, and today she helped me yell at the board of directors. I really, really like her.] Before I accepted the job at Sinclair Holdings, the senior staff had warned me. The man at the top was brilliant, but he had face blindness. Because of his inability to recognize people, he had accidentally fired seven secretaries in the past two years, mistaking them for interns or trespassers. I was the eighth. On my first day, I made sure my massive corporate ID badge was pinned right at eye level. When I walked into his office, I said, "Good morning, Mr. Sinclair. I am your new executive secretary, Jill Gallagher." He had looked up from his mahogany desk, his eyes lingering on my face without truly seeing it, before nodding. "Jill… hard to break, highly valued. Good name." And I lived up to it. My goal in life was simple. Make money. Make a lot of money. 2 I took the corporate job not just for the competitive salary, but for the predictable schedule. Nine to five, with a strict two-hour lunch break. It fit perfectly into my ecosystem of survival. Wake up at 5:00 AM. Drive Uber until 8:30. Clock in at the corporate office at 9:30. Use my two-hour lunch break to run high-surge DoorDash orders in the financial district. Clock out at 5:00 PM. Head straight to the boba shop to shake teas for three hours. Go home, turn on the ring light at 9:00 PM, and stream ridiculous balancing acts for tips. Every minute of my day was monetized. My savings account was finally starting to look like a safety net instead of a countdown to eviction. Everything was going exactly according to plan. Except for the part where my billionaire boss was falling in love with my entire fragmented existence. The Reddit thread was going viral. The comments were getting sharper, the internet tearing into him with glee. “I’m struggling to text one girl back, and this dude is out here assembling the Avengers of crushes.” “Men who perceive every transactional interaction as romantic are a menace to society. She gave you your pad thai, bro, she doesn’t want your hand in marriage.” “If you’re so rich, stop whining on the internet and do something about it. Give the secretary a raise. Drop a grand on the streamer’s live. Tip your drivers.” I was reading that exact comment when my phone chimed with a text from Payne. “Miss Gallagher, your performance has been exceptional. Effective immediately, I am bumping your salary by 30%.” I physically leaped off my mattress. Seconds later, my Uber app dinged. A retroactive $100 tip. Then the DoorDash app. Another massive tip. A DM popped up on my TikTok account. “Hi. I find your content mesmerizing. When are you going live next? I would like to sponsor your stream.” My fingers were visibly shaking as I typed back a response. Then, my phone buzzed again. It was the executive Slack channel. Payne had tagged his chief of staff. “Please arrange for a custom floral arrangement and a cash bonus to be delivered to the boba shop on 5th Avenue tomorrow morning.” The chief of staff replied instantly: “Right away, sir.” I sat on my bed, clutching my head, my brain short-circuiting as it tried to process the influx of cash. After a few minutes of frantic pacing, I opened a burner Reddit account and left a comment on his thread. [OP, ignore the haters. I believe you. I understand exactly what you are going through. You need to follow your heart. Be bold! Show them you’re serious! And remember, the best way to show a woman you care is to support her financially. Throw money at the problem. Do not hesitate!] From that day on, I essentially became the phantom orbiting Payne Sinclair’s entire life. The next morning, I managed to snag his Uber request again. Compared to his cold, detached demeanor the first time, today, the man sitting in my backseat seemed… different. As soon as he got in, the expensive, cedar-and-bergamot scent of his cologne filled the car. His hair was meticulously styled, and his cufflinks caught the morning light. He glanced at the driver profile on the app, then looked up at the rearview mirror, a spark of genuine delight in his eyes. "You're the same driver from yesterday, right?" I kept my eyes on the road, lowering my voice slightly. "Yeah. That's me." Payne’s smile widened, softening the sharp angles of his jaw. "Two days in a row in a city this big. You have to admit, that feels like fate." I had to suppress a snort. Fate had nothing to do with it; it was the sheer, unadulterated finger-speed of a woman who had spent years fighting for the best gigs on the app. I drove with my usual terrifying efficiency, pulling up to the corporate plaza. I tapped my phone screen and turned around. He leaned forward, looking eager. "Do you think I could get your num—" "That’ll be $136," I interrupted, pointing to the app. "Five stars would be appreciated." As soon as he stepped onto the curb, I slammed the gas, ducked into an underground parking garage two blocks away, stripped off my casual driving jacket to reveal my tailored silk blouse, and sprinted into the lobby to clock in. The morning at the office was mostly normal, aside from the fact that I caught Payne staring wistfully at me through the glass walls of his office at least four times. At noon, I hit the streets for DoorDash. Thanks to my aggressive refreshing, I snagged his lunch order from a high-end sushi place. Result: A $200 tip. In the afternoon, I ran a few local courier errands on my way back from a corporate meeting. In the evening, I shook cocktails of sugar and tapioca while Payne stood awkwardly by the register, trying to make small talk before leaving another absurd tip. At night, I went live. A user named "T_SINC" dropped the equivalent of five hundred dollars in digital gifts while I balanced a broom on my chin. It was exhausting, but my bank account had never looked so beautiful. I was counting my digital earnings, my hands practically cramping, when I checked Reddit. Payne had posted a new update. [Loving five women is emotionally draining. But the strangest part is… in my mind, they are all starting to blur together. They’re beginning to look like the exact same person.] Because his previous posts had gone viral, the internet descended on this one like vultures. “The CEO is still at it! Bro, are you just projecting your mommy issues onto a specific type of working-class brunette?” Payne fired back: [I am taking this very seriously. My feelings for all of them are pure.] “Pure? You’re emotionally two-timing five women! You just have a type and you're collecting them like Pokémon.” “If you’ve been pining for this long, make a move. Give your secretary a corporate card. Tell the DoorDash girl you'll pay off her student loans. Drop a grand on the streamer and ask her out to dinner.” Alarm bells started ringing in my head. Sure enough, ten minutes later, a DM popped up on my streaming account from T_SINC. “Hi. You’re incredibly talented. Could we exchange numbers?” I hesitated, my thumb hovering over the screen. But the capitalist in me won out. I sent him a Google Voice number. To his credit, Payne was a complete gentleman. No weird comments, no crossing boundaries. He just asked why I was always streaming so late at night. I typed back, “I have a lot of day jobs. Just trying to stay afloat.” “That’s awful,” he replied. “You have to work all day and stream all night? Your boss must be a tyrant. He sounds like a terrible person.” 3 You have no idea, I thought, nodding to myself. Playing into the algorithm's love for a sob story, I crafted a tragic backstory for my streamer persona. An absent dad, a mountain of medical debt for my mom, a younger brother trying to get through college. A shattered American dream. It worked like a charm. Payne’s sympathy was palpable through the screen. I pressed my advantage. “But it’s okay. Knowing there are generous people like you watching my streams makes it worth it. Your gifts really help.” Payne immediately promised he would be back every single night. “By the way,” he texted. “Can I ask your name?” “I’m… Jane,” I typed back. Over the course of the next month, Payne practically funded my entire existence. He drank enough boba to reach their highest VIP tier. He became a legendary "whale" on the delivery and rideshare apps, known locally as the guy who tipped 200%. He had successfully acquired the contact info for every single one of my alter egos. I interacted with this man in some capacity half a dozen times a day, and thanks to his broken facial recognition, he remained blissfully oblivious. To keep my stories straight, I built a mental spreadsheet. The delivery girl was a broke college student. The streamer was the tragic heroine. But sometimes, the wires crossed. A few days ago, working as his secretary, I had tried to dodge a weekend shift by claiming I needed to visit my sick father. Payne had looked up sharply from his tablet. "Miss Gallagher? Didn't you tell me during your interview that your father passed away when you were seven?" I froze, the blood draining from my face. "My… stepdad. He stepped up." By some miracle of my own fast-talking and his inherent gullibility, he bought it. In fact, my "dedication to my family" only seemed to make him respect me more. Which was great for my paycheck, but terrible for office politics. The other assistants were starting to sharpen their knives. "Jill. Take this contract to the downtown branch." Courtney tossed a heavy manila folder onto my keyboard. She was the quintessential nepotism baby—her father sat on the board of directors, and she treated the administrative pool like her personal sorority pledges. The other girls in the office had warned me to keep my head down. “She’s had a crush on Mr. Sinclair since they were kids. Any woman who breathes his air gets targeted.” I had rolled my eyes at that. “Why target the women? For all we know, he’s not even into girls. Where’s the feminism?” But Courtney didn't care about feminism. She cared about territory. "Did you hear me, Jill? I need this downtown in two hours." I looked out the floor-to-ceiling windows. The sky was the color of bruised iron, and rain was lashing against the glass in aggressive sheets. "It's a monsoon out there. Can't you just use the corporate courier app?" "No. I want you to do it." She crossed her arms, her designer heels clicking against the hardwood. I let out a long, slow breath. "Fine. Open the courier app and request a runner. Put it under the corporate account." "Are you deaf? I said you are taking it." "I heard you perfectly." Without breaking eye contact, I reached under my desk, pulled out my bright yellow rainproof courier jacket, and zipped it up right over my silk blouse. I gave her a dazzling, corporate-approved smile. "Thanks for the gig, Courtney. Good looking out." It was raining, which meant surge pricing. Delivering this folder across town would net me an easy fifty bucks. If she wanted to play petty power games, I was going to get paid for it. As I waited for the elevator, my phone buzzed. A coworker texting me: “Omg, you broke Courtney’s brain. She’s practically foaming at the mouth in the breakroom.” I didn't care. I finished the delivery, internally calculating how I was going to force Courtney to give me a five-star rating on the app, and headed back to headquarters. But the moment I walked through the revolving doors, water dripping from my yellow jacket, my heart stopped. Damn it. Payne was standing in the lobby. What was a CEO doing loitering by the security desks in the middle of a workday? "Jane? What are you doing here?" My breath caught in my throat. I froze, dripping rainwater onto the pristine marble floor. His eyes lit up, and he walked toward me, completely ignoring the security guards. "Are you making a delivery? How is the fund for your brother's tuition going? I meant it when I said I could write you a check." I didn't say a word. Cold sweat mixed with the rain on the back of my neck. He has face blindness. How the hell did he recognize me? "How did you know it was me?" I asked, my voice tight. Payne stopped a few feet away, suddenly looking shy. He shoved his hands into his tailored pockets. "I… I still can't really picture your face. But I remembered the way you stand. The silhouette. And the jacket." The corner of my mouth twitched. I forced a laugh, desperately looking around for an exit route. But the universe hates me, and at that exact moment, Courtney stepped out of the executive elevator. "Jill? You're back already?" Courtney sneered. "Jill? Wait, I thought your name was Jane?" Payne looked between us, utterly bewildered. Courtney was closing the distance, looking ready to cause a scene. Panic seized me. I lunged forward, shoved the signed delivery receipt directly into Courtney’s chest, and inhaled deeply. "Hi, your delivery is complete, please remember to rate five stars—ACHOO!" I let out an ungodly, theatrical sneeze, spraying a fine mist of (fake) saliva in her direction. Courtney shrieked, stumbling backward in horror, wiping at her face. "You are disgusting!" She spun on her heel and sprinted for the restrooms. I slowly turned back to Payne. I gave him a weak, trembling smile. He stared at me, his brow furrowed in deep confusion. "Who exactly are you?"
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