Dreams of Stardom (Hollywood SI)

(Flashback)

"Robyn," a middle-aged woman called out from the seat beside her. "When will you let me meet this boyfriend of yours? I'll be honest with you, I don't like you dating some white boy. I need to see if he's good enough for you."

Rihanna rolled her eyes but didn't look away from the road as she drove her new Audi R8. "I don't think anyone will ever be good enough for you, Mama. And why do you have a problem with his race when Dad wasn't fully black either?"

"He was black enough for me," she said seriously. "Listen, baby girl, and listen carefully. It's not about race; it's always about culture. This boy grew up with serious wealth, but we didn't. His nationality, upbringing, family, and of course, race, is all different from you. No matter what he does or says, there will always be a divide between you two because of that. I know you're a very good singer, and one day you may even surpass him, but that cultural difference will always be there."

Rihanna stayed silent for a few moments, shaking her head slightly. The older woman spoke again before she could counter the argument.

"I know you're stubborn and won't back down. That's why I need to meet this Troy fella to make sure he's good for you."

"He is, Ma," Rihanna lied smoothly, as she had been doing with many people recently. "Would anyone else give me a car like this? And before you ask, he even promised to pay my portion of the taxes on it."

Rihanna's mother, Monica, was an accountant. If she found out Rihanna went bankrupt because of a gifted car, there would be no end to the lectures.

"That's... nice of him," Monica admitted reluctantly before her tone turned suspicious. "But that's something I've noticed about these rich folks. I've done bookkeeping for some very wealthy people, and one pattern always sticks out: whenever a man gifts his woman something expensive, it's usually to cover up something bad—a cheating scandal or something similar."

"Troy's not like that, Mama," Rihanna said hotly. The unspoken truth was that they weren't even dating for real, so it wouldn't technically be cheating if he was with another girl.

"Every man is like that, child," Monica replied gently. "It doesn't help that you're here in California while he's in Britain. Long-distance relationships almost never work out the way you want them to. If you're serious about this guy—really serious—do something about it."

Rihanna glanced at her mother briefly before focusing back on the road. "What exactly do you mean?"

"Either move to London or get him to come here. Permanently."

That was impossible. Troy had [Harry Potter] to shoot, and Rihanna was legally bound to Jay-Z for five more albums, one of which was set to release in April. She could talk to Jay-Z about it, but she loved her career too much to jeopardize it by moving to London. Besides, she had no other connections there. She knew that if she asked, Troy could help her build her career in London, but she didn't want to rely on him for that.

"If you can't do that," Monica continued, "then be mentally ready for the day he cheats on you. Because he will. I know that."

(Flashback End)

That conversation with her mother still echoed in Rihanna's mind whenever she thought about her newly defined relationship with Troy. Deep down, she knew her mother was right: if they stayed continents apart, there was a high chance Troy would cheat on her one day. So, she decided to do something she'd only ever read about in gossip magazines—a one-sided open relationship.

One-sided, because most men wouldn't tolerate their girlfriend being with someone else. Rihanna, however, didn't mind if Troy was with other women while they were apart, as long as he remained emotionally loyal and didn't brag to her about her conquests. She had proposed it for one simple reason—there was no one else in the world like Troy. He checked every box anyone could want in a boyfriend.

And it was only for a few years. Once [Harry Potter] wrapped up, she was confident Troy would want to move to Los Angeles and live with her.

But all of that was a distant future. Tonight, her focus was on the event right in front of her. She felt stunning in her champagne-colored, floor-length Chanel gown. The low-cut dress, with intricate embroidery that looked like it belonged in a museum, was the kind of piece reserved for top models and A-list actresses. Rihanna had the honor of wearing it tonight because she was Troy's date for the Oscars. And since he was the one nominee almost guaranteed to win, it made sense that they'd want his date dressed in something exceptional.

The only lingering doubt in her mind was whether she should have been the one to accompany him to such a prestigious event.

As soon as they stepped out of the car, camera flashes bombarded her, almost blinding in their intensity. Rihanna blinked twice, steeling herself to maintain composure. Meanwhile, Troy appeared completely at ease, waving charismatically to fans, exchanging handshakes and hugs, all while making sure Rihanna was close at his side.

"Hey," he said warmly, taking her hand in his. "Ready to head in?"

He looked effortlessly handsome in a simple yet elegant navy-blue tuxedo with a black bow tie and matching dress shoes. Every major fashion brand had tried to dress him tonight, eager to associate their name with an actor poised to accept at least one Oscar. But Troy had surprised everyone by choosing a tux from an unknown London tailor who valued anonymity over fame.

"Are you sure I should've come tonight, Troy?" Rihanna asked, her happy smile never wavering under the relentless gaze of photographers.

"What are you talking about?" he asked with an easy grin. "If I don't bring my girlfriend to the Oscars, who else am I going to bring?"

"I don't know," she teased. "Maybe your mother? Even Leonardo DiCaprio brings his mom as his date."

"She's my father's date," Troy reminded her. "Remember, he's also nominated tonight for producing [The Perks of Being a Wallflower]."

"Remind me again, why was he nominated for the film?" Rihanna asked curiously. "I thought you produced it on your own."

"I delegated a lot of production work to him," Troy explained. "Well, to Tobias as well. Since I'm a minor, I needed an adult to stand in as a co-producer, so I chose Dad. It's just a technicality."

"What about Evan?" Rihanna asked.

"He's here too," Troy replied. "Just not sitting with me. Each nominee gets two guest invites for family and friends, but if you write to the Academy, they'll give you two more, which is the limit. So, Dad and I both got four guest seats each."

"Who else did you invite?" she asked, curiosity piqued. "In the other five seats, I mean."

"You'll find out soon enough," Troy replied with a mischievous smile. "At least some of them. Dad invited a few friends of his as well that you won't recognize." Then he lead her down the red carpet. Ahead, George Clooney stood speaking with a reporter, his eyes now drifting toward them.

Rihanna was such a huge fan that she struggled to keep herself composed. Her knees felt weak, but Troy's firm grip on her arm grounded her.

"Hey, George," Troy greeted the older man casually, shaking his hand. "Man, I watched your two films this year, and you were incredible in both. I'm sure you're taking home the acting award tonight."

"Not the other ones as well?" George quipped, flashing a cocky grin. "If we're predicting each other's wins, I'd bet you're nabbing Best Original Song."

Rihanna, though a fan, fought the urge to roll her eyes at the lame joke.

Troy ignored it, smoothly shifting the conversation. "Allow me to introduce my girlfriend, Rihanna."

"Hi," Rihanna said curtly, trying to hide her nervousness. "I'm a big fan, Mr. Clooney."

"George," he corrected with a warm smile, before bending forward to take her hand in his. He kissed her knuckles lightly. "You're a lucky man," he said to Troy as he straightened but didn't release her hand, "to have such a beauty by your side."

"Of course I am," Troy said, his tone making it sound like a universal truth. He gently pulled Rihanna closer, forcing Clooney to let go of her hand.

Rihanna glanced up at Troy and caught the possessive glint in his eyes. It was unexpectedly intoxicating. Without thinking, she lowered her hand and gently squeezed Troy's ass. Troy didn't flinch, but the way his smile widened, she knew he'd gotten the message that she liked this behavior of his.

Clooney chuckled and offered them both a nod. "Well, I think I should head inside. It was nice meeting you, Troy, Rihanna."

He turned and walked away.

"So, Troy," the reporter, who had remained mostly quiet until now, said eagerly, "how do you feel about your win for Best Original Song tonight?"

Troy turned to her with his signature grin. "I've had a few weeks to process the idea, so it doesn't feel like much of a surprise anymore. I'm sure most of the other nominees will feel that way too."

"What about the other categories you're nominated in tonight?" she asked.

"I'm not winning anything else tonight," Troy said jokingly. "I mean, if I saw a teenager other than me with two Oscars already under his belt, even I wouldn't vote for him." The three shared a laugh before Troy continued, "Jokes aside, I'm humbled to even be nominated. If we win, that'll just be further acknowledgment from our peers, and we'd be honored to have it."

Before any more questions could be directed at them, Troy smoothly guided Rihanna inside the Kodak Theatre.

"Troy! Rihanna!" a familiar female voice called out as they stepped in. The speaker was Emily—better known to the audience as Emma Stone.

"Hi, Emily," Troy said, releasing Rihanna's arm to give Emily a warm, gentle hug. "Glad you could make it."

"Of course! How could I not?" she replied playfully before turning to hug Rihanna. "Thank you for inviting me, by the way. Never in my wildest dreams did I imagine I'd be seeing the Oscars in person."

Troy inclined his head modestly. "Mark my words, one day you'll win one of these if you keep up the amazing work you've been doing."

Before she could respond, another voice joined in.

"Hey, guys!" Emma Watson greeted, arriving with Jamie Bell and Evan Spader in tow.

As the group grew, Rihanna quickly pieced together who the other guests were. Emma and Jamie were clearly two of Troy's additional invitees, along with Emily and Evan. It seemed strange that Troy would invite his ex-girlfriend to such an event, but the realization dawned on her: [The Perks of Being a Wallflower] was nominated for several awards, including Best Picture. Emma Watson was likely invited by the studio, and Troy had probably extended his invitation to Jamie to round out the 'Golden Trio'.

Her theory was further supported when Jonathan Groff joined the gathering. Since he wasn't particularly close to Troy, Rihanna reasoned he must have been another guest of the studio.

"Let's head to our seats," Troy announced after a few moments of conversation. "The show's about to start, and believe me, you don't want to lose your spot to those seat fillers they employ."

As the others filed toward their assigned seats in the middle and back rows, Troy and Rihanna were escorted toward the front, where the A-listers were seated. Troy's spot was in the very first row, which made sense—he was undeniably an A-lister, unlike his teenage friends. Emma Watson was the closest to that status but hadn't yet proven herself outside films where Troy held the lead role.

Everywhere Rihanna looked, she saw Hollywood royalty: Meryl Streep, Jake Gyllenhaal, Reese Witherspoon, Charlize Theron, Steven Spielberg, and so many more. These were the absolute elite, and Rihanna was acutely aware of just how surreal this moment was.

"Hey, do you recognize me?" a voice called out to Troy.

He turned immediately and broke into a wide smile at the sight of Michelle Williams standing nearby with a handsome man at her side—Heath Ledger.

"Michelle!" Troy exclaimed, standing up and embracing her warmly. "I can't believe it's been so long."

"It is so good to see you too, Troy," Michelle said with a warm smile. "I can't believe you've grown up so much. You even have a girlfriend now."

"This is Rihanna," Troy introduced her smoothly. "Rihanna, this is Michelle Williams. She played my sister in my very first film, [Sex Education]."

Michelle smiled warmly, holding onto her partner's arm. "And this is my partner, Heath."

Troy extended a hand to Heath. "It's a pleasure to meet you. I just love everything you do."

"You do?" Heath asked, raising an eyebrow with a hint of skepticism.

"Yes," Troy said with genuine enthusiasm. "[10 Things I Hate About You], [Monster's Ball], [Ned Kelly], and now even [Brokeback Mountain]—I've seen all your work. Honestly, I'm baffled you haven't won an Oscar already."

Heath chuckled modestly. "You flatter me too much. I'm not that good."

"Yes, you're better," Troy said earnestly. "Say, Michelle, Heath, if you guys are ever in London, come stay at my place for some time. You can even bring your daughter. I would love it."

"We would love that too," Michelle replied for the both of them.

"Ladies and Gentlemen!" boomed a voice from the speakers before the conversation could continue. "Please take your seats; the ceremony is about to begin."

Troy asked Michelle, "Where are you two seated?"

"Right beside you two," Michelle replied, pointing to the seats with their name cards attached. With that, the four took their respective seats.

Rihanna grasped Troy's hand excitedly as everyone quieted down. Moments later, a short clip played about the difficulty of finding a host for the Oscars. The humor fell flat, leaving the audience's reactions lukewarm.

Then Jon Stewart, the host, took the stage and launched into his monologue.

"Thank you, everyone. I'm so excited to be here," Stewart began. "Ladies, gentlemen, Felicity."

The audience erupted in laughter at the jab at Felicity Huffman, who had portrayed a transgender in [Transamerica].

As Stewart continued his jokes, the crowd laughed sporadically. He riffed on politics, movies, and even piracy.

"To the people involved in piracy, don't do it. Just look at these faces, these innocent people. Look at them!"

The camera panned directly to Troy and Rihanna. Without missing a beat, Troy pulled a wide-eyed, mock-innocent expression as if he might burst into tears at any moment. Rihanna struggled to keep her laughter in check at his theatrics.

"Look what you've done!" Stewart continued. "There are women here who can barely afford enough gown to cover their breasts."

Rihanna felt a jolt of flustered embarrassment as the camera lingered on her, highlighting her plunging neckline. Just as she was starting to feel uncomfortable, the camera shifted to Michelle Williams, saving her from the moment.

"There are some really big stars here tonight," Stewart continued. "The man himself, Mr. George Clooney—triple nominee for writing, acting, and directing."

The crowd erupted in polite applause.

"And then there's Troy Armitage," Stewart said, turning his gaze directly to Troy before continuing, "Nominated a total of six times tonight in four different categories: acting, producing, music, and song. If we add all of Troy's nominations and wins together, it would be greater than the number of years Troy went to school."

Troy laughed heartily at the playful jab about his education, which was true because Troy had finished his schooling when he was very young.

"It's the first time since 1969 that a single person is guaranteed to walk away with an Oscar before the ceremony even took place," Stewart added, his tone both teasing and reverent.

This time, the applause was thunderous as the audience fully grasped the historic significance of the moment. Troy responded with a gracious bow of his head toward Stewart, silently thanking him, before the host moved on with his monologue.

The best part about Jon Stewart's monologue was that it never veered into cruelty. All his jokes were lighthearted, harmless fun, which the audience clearly appreciated. No one was singled out in an uncomfortable way, and the atmosphere remained celebratory.

When Stewart wrapped up his segment, the show transitioned to the first award of the night: Best Supporting Actor.

As Nicole Kidman stepped gracefully onto the stage, Troy leaned closer to Rihanna and whispered, "George Clooney."

True to his prediction, Nicole read out the same name moments later.

Rihanna's longtime crush ascended the stage to accept his award, delivering a smug speech. He began by referencing his title as the "sexiest man alive" in 1997 and then pivoted to a tongue-in-cheek boast about how the Academy and Hollywood were perfectly in tune with the real world and calling them out of touch was false.

By the time he finished, Rihanna leaned closer to Troy and murmured, "I'll be honest with you, I used to have a crush on him, but after today, I can't help but think he's an asshat."

Troy chuckled softly, shaking his head. "That's why they say, 'don't meet your heroes.'"

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