Dating the Heir She Called Broke

Shane practically dragged me into this blind date. He swore she had it all: old money, drop-dead gorgeous, five-foot-seven, and curves in all the right places. Unable to weather his relentless badgering, I finally caved and agreed to the dinner. Halfway through the meal, she excused herself to the powder room. She never came back. Wondering what on earth had happened, I pulled out my phone to text Shane. But as soon as I opened my feed, a viral local post hit my screen. [Truth or Dare with my crush: had to go on a blind date with an undercover gold-digger. Here’s the tea!] A cold knot tightened in my gut. I tapped on it. The very first picture was of me, head down, quietly cutting my steak. [A broke scrub trying to play the high-roller. Right out of the gate, he ordered two vintage bottles, practically drooling to get me hammered so he could crawl into my bed.] [He called it a blind date, but he clearly just wanted a shortcut into high society.] [A four-thousand-dollar tasting menu? The audacity of this freeloader.] The comment section was already past ten thousand, everyone screaming at her to run. She had pinned her latest update right at the top. [I ran, guys! Hanging out with my crush right now.] [He is honestly the sweetest. He dared me to go on the date with that deadbeat, but then he spent the whole evening getting jealous.] [Looks like we’re finally making it official tonight~] Attached was a crystal-clear photo of her, nestled comfortably in Shane’s arms. A dry, bitter laugh ripped from my chest. I locked my screen, brought up my contacts, and called my executive assistant. "Cancel Shane Larson’s final round interview. Reject his application immediately." "Also, revoke his access to the downtown penthouse I let him crash in, and have the transport team repossess the McLaren I bought last month." Without me funding his life, I wanted to see which one of us was the real gold-digger. … Setting the phone down, I looked at the lavish spread across the table and shook my head, amused by the sheer absurdity of it all. I’ve never liked owing anyone anything. While waiting for Bridget Hughes to arrive earlier, I had already settled the entire bill. And yet, in a matter of minutes, I had been branded an opportunistic parasite for the whole city to mock. My appetite vanished. Disgusted, I pushed my chair back and prepared to leave. Before I could clear the table, the server stepped into my path, a brittle smile plastered across her face. "Excuse me, sir. There’s an outstanding balance of eight thousand dollars on this table. How would you like to take care of that?" I paused, raising an eyebrow. "I paid for the tasting menu before we were even seated." Her brow furrowed, the professional facade slipping into outright disdain. "I’m sorry, sir. But the lady who was dining with you took two bottles of imported vintage reserve on her way out. She specifically told us you’d be handling the check." She tilted her chin up slightly. "You aren't about to pretend you don't know her, are you?" The open malice in her tone was unmistakable. I kept my voice flat and icy. "Since you saw her carry them out, you should call her back to settle it. That has nothing to do with me." I stepped around her, but she lunged forward, grabbing my wrist tightly. "Leaving in such a hurry? Rushing out to split the spoils with her?" She raised her voice, deliberately projecting across the dining room. "Sir, drop the act! Pay the bill right now!" Dozens of heads turned from surrounding tables. Whispers broke out like a rustling breeze. "Look at him. Dressed so clean, but pulling cheap hustles like that." "They’re definitely in on it together. She walks out with the vintage stuff, and he feigns ignorance to skate on the bill." "Eight grand in wine? Nobody does that by accident." At a booth nearby, an older woman in a plunging neckline gave me a slow, predatory once-over. "Handsome, it’s only eight grand. Need me to cover it for you?" She took a sip of her martini, smirking. "You wouldn't even have to pay me back. Just spend the night keeping me company." A wave of nausea hit the back of my throat. Ignoring her, I unlocked my phone and opened Bridget Hughes’s chat window. [You walked out with eight thousand dollars worth of reserve wine. Get back here and pay for it.] A moment later, a payment notification popped up. A Cash App transfer for $0.52. Followed by a message: [You do this a lot, don't you? Scrounging free meals under the guise of blind dates?] [How does it feel getting played at your own game?] [Consider that fifty-two cents an act of charity. Feel free to screenshot it and flex on your feed.] I sent back a single question mark. The red exclamation point appeared instantly. Blocked. Almost simultaneously, the viral post refreshed. [You guys called it! The deadbeat actually came crawling back to demand money from me.] [Consider those two bottles my early wedding gift to my crush and me.] The new photo showed two crystal glasses clinking together over the neck of the expensive reserve. The comments were eating it up. [OMG, queen move! Put the scammer in his place and locked down her man at the same time! Two birds, one stone!] [I wonder what that bum is doing stuck at the restaurant right now lmao. You think he’s hitting on random women at nearby tables just to get his bill paid?] The server tapped her foot against the hardwood, her patience entirely gone. "Sir, we don't have all night. Eight thousand dollars is grand larceny. If you don't pay immediately, we are calling the police." The police? A humorless grin touched my lips. "Go right ahead. Call them." The server froze, clearly caught off guard. The spectators fell quiet, sensing the sudden shift in the air. I crossed my arms and stayed put. "The food and reservation totaled over five thousand dollars, and I paid it in full before sitting down. Now you're accusing me of colluding in theft? Where is your proof?" Her face paled a fraction. "I never touched those bottles," I continued, voice cutting through the quiet room. "Yet you corner me and demand eight grand. Am I not entitled to suspect that you and that woman are working a scam together?" She stumbled back a step, flustered. "You—you're just twisting words because you're broke! Fine, I'm calling!" She stormed back to the host stand and dialed 911 on the landline. Just then, a hand caught my sleeve from behind. The woman from the booth leaned in, reeking of expensive perfume. "Honey, why make this so ugly? I told you, I can take care of it. A body like yours is easily worth eight grand." I turned, cold fury flashing in my eyes, and smacked her hand away with a sharp crack. "Remember what you just said. When the officers arrive, you can explain your proposition to them." Her face flushed crimson, and she stepped forward aggressively. "I was trying to help you, you ungrateful little—" Her words died in her throat. Her eyes locked onto the platinum crest pinned to my lapel, and all the color drained from her skin. "You... what is your relationship to the Prescott family?!" The heirloom crest was a piece passed down through generations of Prescott Holdings. Anyone moving in the city's highest financial circles knew the unspoken rule: whoever wore that crest was the designated heir to the Prescott empire. I didn't answer her. Cold sweat beaded on her forehead as she waved her hands frantically. "I—Mr. Prescott! Please forgive me, I was utterly blind! My name is Alison Stone, I'm a Vice President at Far Horizon Capital..." Seeing that I offered no response, she dropped her voice to a desperate whisper, leaning closer. "That girl who just left—I know her! Her name is Bridget Hughes. She’s the illegitimate daughter the Hughes family only acknowledged a couple of months ago!" Hughes's illegitimate daughter? The memory clicked into place. My father had mentioned it offhandedly over breakfast last week: "An out-of-wedlock kid they just brought home, and Hughes already has the nerve to float an arranged marriage alliance with us? Since when does my son need to settle for Robert Hughes’s desperate bids for legitimacy?" So she was Bridget Hughes. The irony was almost poetic. If my father found out she had publicly dragged his only son through the mud, he would terminate every joint venture with the Hughes Group by morning. Her days as an acknowledged heiress were already numbered. My phone vibrated in my palm. It was Shane. "Jack?! You called the cops?!" His voice screeched through the speaker. "Are you out of your damn mind?! Over two bottles of wine?!" Listening to his frantic shouting, the caption on Bridget’s post echoed in my mind: [He dared me to go on the date with that deadbeat, but then he spent the whole evening getting jealous.] A dark, hollow disgust settled over me. If he wanted Bridget, why not just pursue her? Why engineer this elaborate humiliation just to drag me through the dirt? Had I ever treated him poorly? When he was broke in college, I had my father’s charity foundation quietly set up a monthly stipend for him. After graduation, when he complained that entry-level jobs paid pennies for too much work, I forwarded his resume directly to our chief talent officer with a simple note: "A personal friend. Fast-track him." Four days a week, easy workload, a six-figure salary. I had never flaunted my family’s empire in front of him, but he knew damn well how much he owed me. And this was how he repaid it? "Jack, tell the restaurant to drop the charges right now!" Shane’s voice hammered through the line. "It's just wine! It's not like you can't scrape the money together! I set you up with Bridget out of the goodness of my heart! I'm your best friend—could you think about my feelings for once?!" "Out of the goodness of your heart?" My voice was lethal, measured. "Shane, as of tonight, we are done. That sports car I signed for? Cancelled. And pack your bags out of my penthouse tonight before I have building security change the locks." There was a beat of silence on the other end, followed by a low, mocking chuckle. "Jack, stop throwing a tantrum. If you keep pushing this, everyone’s going to find out what really happened back in college." He paused, his tone dropping into that familiar, suffocating pseudo-concern. "Did you forget? I was the only person in the world who stood by you. Without me, who’s going to believe a word you say?" A chill crept down my spine. "What really happened?" Unbidden, memory dragged me back to sophomore year. A fraternity mixer. I barely drank half a glass, yet somehow, I blacked out entirely. The next morning, photos of me were plastered across the campus forum. I was slumped over a table, flushed and disheveled, framed at intimate angles surrounded by several female classmates. The comments had been brutal. [Isn't that the quiet freshman everyone thought was so refined? Turns out he’s completely reckless.] [One drink and he’s ready to go home with anyone? Guess I should've made a move.] [Acts all proud and untouchable, but he's easy prey.] I had been trembling, terrified, and I ran straight to Shane. He had hugged me, tears in his eyes, cursing the people who took the photos. "Don't be scared, Jack. I believe you! Let me handle this!" That night, he went live on social media, putting on a grand show of defending me: "Is it fair to tear Jack down over a few photos?! Sure, he was sitting with multiple girls, but he’s just naive! He doesn't know how to set boundaries! And his alcohol tolerance is terrible—you can't blame him for getting sloppy off one drink! I know deep down he isn't a bad person!" Back then, I was too young to catch the poison wrapped in his defense. I thought he was protecting me. I spent years treating him like a brother out of gratitude. Now, the haze cleared. Shane had been by my side the entire night. He was the one who framed those photos. He was the one who leaked them. He had always operated this way—stepping on my neck just to elevate his own halo. I exhaled slowly, my voice stone-cold. "Shane. I didn't do it back then, and no matter how many lies you tell, you can't make it real. Tell Bridget Hughes that if she doesn't drag herself back here and pay for that wine, she will live to regret it." I hung up without waiting for his response. The server finished her call, standing nearby with her arms crossed smugly. "Just wait right there." Alison Stone stepped forward, eager to redeem herself. "What is your attitude? It's just eight thousand dollars! I'll pay it!" Without looking at her, I snapped, "Be quiet." She flinched and retreated immediately. The server let out a dry sneer. "No wonder the lady called you a freeloader. You haven't been abandoned for ten minutes and another woman is already opening her wallet for you. What a performance." I didn't dignify her with a glance. Instead, I refreshed the post on my phone. [The deadbeat called the cops! Lmao, he’s demanding I go back. Doing whatever it takes to latch onto my money.] A new comment sat pinned at the very top: [I know him personally. He’s always been this kind of parasite.] The avatar was identical to Shane's. The comment section erupted into a frenzy. [Holy crap, someone with real receipts? It's confirmed!] [Spill the tea! We want more details!] [Expose this loser to the entire city!] Within minutes, my full name and that blurry, years-old college photo were posted in the replies. My chest tightened, a familiar disgust churning in my stomach. I copied the link and forwarded it straight to my father. [Ask Robert Hughes how he plans to settle this.] Less than thirty seconds later, my phone rang. My father’s voice thundered through the line, vibrating with barely contained rage. "Insolent bastards! Jack, they don't get to settle this quietly. Stay right there. Dad is on his way!" Hearing his voice, the tension in my shoulders began to ease. Ten minutes later, the brass entrance doors swung open. Bridget Hughes sauntered back inside, oozing arrogance. "You're really something, aren't you? Actually calling the cops. Tell me, how much hush money are you trying to extort?" My brow furrowed. "I have zero interest in your money. Save your breath for the police." Before she could fire back, Shane scurried in behind her, his eyes rimmed with theatrical red. "Jack, you kept begging me to introduce you to an heiress! Bridget is the best connection I could possibly offer you!" He sighed heavily, pitching his voice for the room to hear. "She wasn't interested, but that’s out of my hands! If you hadn't ordered such ridiculously expensive food right off the bat, you wouldn't have scared her away!" Instantly, the murmurs in the dining room shifted. "I knew it. A girl like that wouldn't bolt for no reason. She clocked him as a gold-digger immediately." "Begging his buddy to hook him up with an heiress? Look in the mirror first, man." I let out a harsh laugh. "The issue at hand is the two bottles of wine she stole while sticking me with the bill." I turned toward the server. "When the officers get here, make sure your manager pulls the security footage." "Check the cameras?" Bridget scoffed. "Do you even know who I am? Who gives you the right to investigate me?" Right on cue, the general manager hurried out from the back office. "No need, no need!" He turned toward me, his expression harsh and dismissive. "Our security system is undergoing maintenance. The cameras are offline! Look, Ms. Hughes is not someone you want to cross. It's a minor dispute—there's no need to drag the police or camera footage into this." I smiled thinly. "If it's such a minor dispute, whoever took the wine should pay for it." Bridget’s face darkened. She reached into her designer clutch, pulled out a stack of hundred-dollar bills, and snapped them violently against my face, one by one. "At the end of the day, you just want cash. Jack, here's five hundred bucks. Enough for a scrub like you to fund your next three blind dates." She hooked her arm around Shane’s waist, turning to leave. "Take the cash and get lost. Don't ruin my night any further." Five hundred dollars? I drew a long breath, picked up the heavy leather billfold from the table, and slammed it hard against the back of her head. "Trashy, unacknowledged bastard," I said, every word dripping with ice. "Steals eight thousand dollars of wine and thinks five hundred covers it." "What did you say?!" She whipped around, her eyes wild with fury. "Who the hell are you calling a bastard?!" She lunged, digging her acrylic nails into my collar, aiming for my throat. "Say it again! I'll make sure you don't leave this building alive!" Alison Stone finally broke through her paralysis, shoving Bridget back. "Are you insane?! How dare you lay a hand on him?!" Shane gasped loudly, stepping back and covering his mouth in exaggerated shock. "Jack... who is this woman? You really are incredible. Five minutes alone and you've already found another woman to fight your battles. No wonder all those girls were all over you in college." He tilted his phone screen toward the crowd, displaying the old college photo glowing brightly in the dim light. The room erupted. "Surrounded by women while passed out... he was definitely faking it." "Clearly trying to seduce someone." "A degenerate back then, a grifter now." Bridget recovered her footing and shoved my shoulder hard. "Let me tell you something: going on this date was just a joke between Shane and me. A lowlife like you thinks he can step foot inside the Hughes family? Keep dreaming!" She pulled another thick stack of cash from her purse and slammed it onto a nearby table. "Anyone who pins this bastard to the floor gets every dollar on this table!" That stack was at least three thousand dollars. A collective breath caught in the room. Greed flickered across several faces. "I got him!" "Ms. Hughes, let me!" Before I could brace myself, someone shoved me hard from behind. My foot slipped, and my knees crashed heavily against the hardwood floor. Pain shot up my legs. I gritted my teeth. "You know this is felony assault, don't you?!" "Felony?" Bridget laughed coldly, looking around the room. "This restaurant partners with the Hughes family. Who here is going to call it a crime?" She pointed down at the bills scattered across the floor. "Keep him on his knees. Make him crawl and pick up every bill while shouting, 'I am a broke gold-digger.' If I'm entertained, I'll double the payout!" Instantly, a heavy hand clamped down on the back of my neck, while another man drove his knee into my lower back, pinning me flat. "Pick it up!" "Come on, yell it! It's not like she's lying!" From the corner of my eye, I caught the cruel, triumphant smirk spreading across Shane’s face. Then, the heavy front doors slammed open with a thunderous crash. "Outrageous! I’d like to see who has the guts to make Thomas Prescott's son kneel!" I lifted my head. Standing in the doorway was my father, his face dark as a storm cloud. And trembling right behind him was Robert Hughes.