The Long Game

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The Long Game
Summary
To put an end to Bruce’s relentless attempts at setting him up with the sons and daughters of Gotham’s wealthiest families, Jason agrees to a plan cooked up by Roy. The idea? Start fake dating. It’s foolproof, Roy insists—wouldn't it be funny either way?Jason will find himself unexpectedly caught up in his own emotions, panicking as feelings he didn’t anticipate bubble to the surface.
All Chapters Forward

Lian, The Chatty Cupid

Tim snickered as Duke clutched his stomach, dangerously close to collapsing to his knees as he wheezed for air. “Fuck!” Duke sniffled through a tear, face red and body trembling with laughter. “Who was she? And how did you even convince her to do that?”

A devilish grin spread across Tim’s face as he casually pulled out his phone and held it up like a trophy. “Cash,” he said simply, shrugging as if bribery were the most obvious solution in the world.

Duke blinked. “Ohhh,” he mouthed, nodding in understanding. “Yeah, okay, makes sense. But, like—seriously—who was she?”

Tim’s smug demeanor faltered as his gaze shifted over Duke’s shoulder. Approaching them with a slow, deliberate stride was Cassandra, her eyes boring holes into him like twin lasers. Duke didn’t need to turn around to feel the sudden shift in the atmosphere. A chill ran up his spine as his expression crumbled in horror. “No… don’t tell me…”

As if on cue, Cassandra was walking their way, and behind her, in a fit of unrestrained, tear-inducing laughter, was none other than Stephanie Brown, who dramatically ripped off a wig like she was unveiling a masterpiece. 

It was her. The woman who had been tasked with sidling up to Roy Harper and making him squirm with disdain. Duke’s jaw dropped. 

“Why??” Duke hissed, whipping around to glare at Tim, his voice somewhere between disbelief and betrayal.

“Well, she agreed to do it!” Tim shot back defensively, holding up his hands like he was the victim. “Plus, I couldn’t exactly bring a random hired actor to a gala, Duke! C’mon!”

“YES YOU CAN!” Duke exclaimed as he started shifting on his feet.

“Okay, makes sense,” Tim suddenly nodded. “You absolutely got me there.”

“But instead,” Duke growled, his face contorted in exasperation, “you made Steph, of all people, go undercover to hit on Jason Todd’s boyfriend?! Are you insane?”

Tim rolled his eyes and grabbed Duke’s arm. “Okay, first of all, Jason and Roy are not boyfriends. Not officially! Not yet! One of them is in denial and one is definitely planning something—”

“Doesn’t make it better!” Duke interjected, wrenching his arm free. “You’re dragging me into this mess, and I don’t wanna be in Cass’ line of fire, man.”

“Oh, don’t act like you didn’t enjoy the show!” Tim hissed, pointing an accusatory finger. “You were laughing so hard, I thought you were about to pass out!”

“Yeah, and now I’m gonna catch a ride to heaven!” Duke wailed, stumbling backward, putting as much distance as possible between him and Tim. “I don’t want her kicking my ass in sparring!”

Cass, who had been silently watching the exchange as she got closer, tilted her head. Then, with unnerving calm, she walked right up to Tim. He froze, like a deer caught in headlights.

She leaned in, her breath tickling Tim’s ear. “Check messages,” she whispered ominously, then turned on her heel and walked away, rejoining Stephanie, holding her ever so gently as Steph kept stumbling as she laughed.

Tim blinked. “Huh. That went… better than expected.” He couldn’t help but grin. “Maybe she’s not mad after all.”

But the hairs on the back of his neck suddenly stood up-Tim couldn’t shake the feeling that something was still very, very wrong. 

BZZZT. BZZZT.

Tim’s phone buzzed in his pocket. His smile grew as he saw who it was. “Kon!” he exclaimed, practically skipping toward the balcony for privacy. “Yes, you miss me or somethi—”

“Timothy. Jackson. Drake.” Kon’s voice growled through the line, tone dripping with fury.

Tim froze mid-step, his grin vanishing instantly. “Uh… hi?” Tim greeted weakly, praying Kon’s anger wasn’t as bad as it sounded.

“Are you fucking with me right now?!” Kon barked, his voice growing louder.

Tim frantically unlocked his phone, remembering Cass’s cryptic warning. His fingers fumbling as he scrolled through his messages, heart racing. Finally, he landed on an image Kon had sent in their messages a few minutes earlier.

His soul had left his body.

“Wait! I can explain!” Tim stammered, eyes glued to the photo that had just ruined his life. It was taken over a year ago at a gala—back before he and Kon weren’t dating yet. In the photo, Tim was clearly flirting with a group of attractive partygoers his age. Worst of all, there was a lipstick mark on his neck. 

“Kon! It’s not what it looks like!” Tim pleaded, scrambling for damage control. “This was before we were dating! I was just working on a lead! It’s—”

Click . Kon hung up.

Tim stared at his phone, his expression blank as the full weight of his situation hit him. He was so dead. 

In a daze, he turned his head, seeking solace from Duke. But he looked like he’d just been struck by lightning. Duke was holding his phone with trembling hands, his eyes wide as saucers. 

“Duke?” Tim asked cautiously, desperate for a distraction. “What’s wrong?”

Duke slowly turned his screen toward Tim. The headline read: “Signal, Gotham Hero Spotted on Grindr: A Deep Dive.”

“Oh, holy shit. She really got Barbara to help,” Tim whispered, biting down on his lip to keep himself from laughing out loud. “At least I can do my boyfriend a favor–I mean explain myself. You, on the other hand…”

“Shut up,” Duke groaned, sinking to the ground as if he were physically melting into the floor. “The hero image that I’ve built… down the drain. Just like that!”

Tim patted him on the shoulder, trying not to snicker. “Good luck, buddy. You’re gonna need it.” And with that, he vaulted over the balcony railing and disappeared into the night.


 

“What the hell was that?” Roy huffed as they snuck into one of Jason’s hideouts, out of breath from dodging paparazzi like they were bullets.

Jason rolled his eyes, fighting his heart to remain composed. “And what the fuck took you so long? I was this close to being auctioned off to heirs like a designer handbag at a charity auction!” He groaned as he stretched his back “You fucking owe me.”

Roy scratched the back of his head, wincing as he flopped onto the couch. “Alright, alright! It’s my bad, I admit it. I just got distracted, okay?”

Jason's eyebrow shot up, his expression sharp with disbelief. “Distracted? Are you kidding me? What was the call about?? And was the girl that pretty for you to be love struck!”

Roy winced, scratching the back of his head. “It was...uh… Dinah.”

Raising an eyebrow, Jason calmed down as he breathed out. “What is it?” He asked with concern. “Is it Lian? Is she okay?”

“No, no. She’s completely safe!” Roy smiled as Jason gave a relaxed sigh. “It’s Oliver.”

Jason grimaced at the name. “What’s it about your old man?”

“He’s not my old man,” Roy groaned, dragging a hand down his face. “Apparently, Lian’s been asking Oliver and Dinah about marriage. I guess she got the idea from that whole conversation we had. But when they asked why she was curious, she brought us up.”

Jason's face fell. “Ah... shit.”

“Yup.” Roy sighed heavily. “Now Oliver’s flying in. He’s gonna be at Bruce’s manor tomorrow.

“Fuck! ” Jason shouted, throwing his head back. “This whole thing can’t get any worse.”

“Yea…”

Jason growled, pacing. “Forget Oliver for a second—who the fuck was that woman? Was she really that hot for you to go completely brain-dead and leave me to fend for myself?!”

If Jason were to be honest, he didn’t understand why he was so frustrated at the fact that Roy got distracted with a woman. He wasn’t that angry about the call to begin with–he was just annoyed at the fact that Roy was at such a close proximity with someone else. His heart felt heavy, but he had to bury it.

“Hey! Let me defend myself for a bit here!” Roy blinked, momentarily stunned by the intensity of Jason’s outburst.

Jason crossed his arms, glaring. “Oh, this better be good.”

“It was... Steph,” Roy admitted, grimacing.

Jason’s brow furrowed. “Huh?”

“Yup.” Roy sighed. “In some half-assed disguise. She kept saying, ‘Bitch, just pretend with me here!’ and started throwing random quotes at me. It was weird. ”

Jason’s eyebrow shot up as he let out a big sigh. One didn’t need to be a detective to figure out what the hell just happened. “Tim fucking Drake,” He snarled as he tore off his suit and forcefully ruffled his hair, trying to get rid of the hairwax that was lathered on him. 

Roy snorted. Sneaky little bastard.”

“I’m definitely going to get even with that sneaky bastard–”

“Whoa, hold that thought.” Roy held up a finger, his lips twitching as he scrolled on his phone. “Shit’s wild right now. Check the news.”

Still battling his cemented hair, Jason unlocked his phone with his free hand and snorted so hard he nearly choked. The headlines were a circus:

  • Signal Allegedly Found on Grindr: Superhero or Super Swipe?
  • Tim Drake Photographed in Emotional Breakdown: ‘Mystery Partner’ Speculation at an All-Time High

Jason wheezed, practically collapsing onto the couch. “I’m betting Cass had Barbara pull this shit.”

“Didn’t know Cass could be this brutal,” Roy whistled as he tapped another article. “Oh look! Your love confession for me is trending. The comments are gold, man.”

Jason glared daggers at him and swatted the phone away. “You fucker. This is all your fault!”

“Yeah, yeah,” Roy grinned. “I’ll make it up to you. Dinner? Movie? Matching tattoos?”

“I’m never living this down," Jason groaned, slumping deeper into the couch with his shirt half unbuttoned and boxers peeking out. "Assholes. I’m surrounded by assholes.”

“Yeah,” Roy said with a smug grin. “You won’t admit it but you like having me around, though.”

“Whatever,” Jason grumbled, glaring at the ceiling as if it had personally wronged him.

Roy’s grin widened. “So, uh...how are we gonna spin this to Bruce? Think he’ll buy it?”

“Wasn’t this your genius plan? You fix it.”

Roy cocked an eyebrow, his grin turning devious. “Just leave it to me.”

Jason leaned on him, exhaustion taking over. “I swear to God, if all my hair turns white from this stress, I’m shaving it off and blaming you.”

“Sounds like true love, babe,” Roy laughed.


 

Jason woke up in his room in the Wayne manor, which was odd. He was sure he and Roy were in one of his hideouts just last night. Not only that, it was the first time he had slept that well ever since he came back to life.

“Is it the body warmth? The stress? Or something else entirely?”

"Morning, Sunshine." Dick stood with his arms crossed, looking far too judgmental for Jason’s liking.

“What do you want?” Jason grumbled, covering his eyes with his arm like he could wish Dick away by sheer willpower. “It better be important—”

“Oh, it’s important, alright!” Dick exclaimed, pacing dramatically. His hands flailed as if he was a drowning duck. “I knew he liked you! But seriously! He seriously went after his best friend's little brother!” He jabbed a finger toward Jason. 

Jason blinked, completely unfazed. “That’s cute. Real dramatic.” He sat up, scrubbing a hand through his hair. “Where the fuck is Roy, anyway?”

Dick huffed, pacing even faster. “Being interrogated by B.”

Jason froze. "Oh for fuck’s sake."

“Yeah,” Dick continued with a grim nod. “Bruce is making him explain himself. Had to leave before I get dragged into it for dating Wally.” Dick grimaced.

Jason groaned and flopped back down onto the bed. “Roy better not fuck this up.”

“Oh, he’s gonna fuck it up,” Dick assured him, hands on his hips.

Jason stared blankly at the ceiling. “Great! Just great.”

“I think Dinah called though, she said that Lian wanted to talk.”

At the mention of Roy’s daughter, life suddenly came into Jason’s eyes. “Oh? I wonder what she’s calling for?” He pondered loudly as he got out of bed and got dressed. “Probably missing Roy... I gotta make it up to her somehow.”

Dick cocked an eyebrow and smirked, “Now, now. Since when was our Jason so domestic? The mighty RedHood—now a family man?”

Jason flipped Dick off without missing a beat. “Go adopt another circus brat,” he muttered, tugging on his boots before stomping toward the stairs. Excited and annoyed in equal measure, he was looking forward to seeing Lian’s face but not to whatever mess Roy had probably made trying to deal with Bruce. “He better not have fucked up—”

“They want to get married! Dad also asked me how I feel about having Jason as a father!” a shrill, triumphant voice suddenly boomed through the manor. “They’ve been talking about it! Friends who fall in love are supposed to get married! Dinah said so! I love Jason staying with us! Please, Grandpa Bruce!”

Jason froze mid-step, the color draining from his face. What?!

He burst into the Batcave to find Bruce standing by the giant monitor, arms crossed with furrowed brows. Roy was next to him, wearing what could only be described as the world’s guiltiest smile, while Lian’s grinning face continued to glow on the screen like an innocent little angel.

“Oh my gosh,” Dinah's voice crackled through as she gently cupped Lian’s mouth in a last-ditch damage control effort. “Oops!” she said sheepishly, giving Roy an apologetic(?) wink before abruptly ending the call like it was a hostage situation.

Bruce’s eyes slowly shifted to Jason, ignoring Roy entirely. “How long?” he asked coolly, as though calculating their jail sentence. And who he needed to make disappear.

Jason blinked, mind scrambling. “Umm… surprise?” he offered weakly, shooting a withering glare at Roy.

Roy seemed to have been grinning for a second–Jason wasn’t sure if he saw right. Jason opened his mouth to unleash verbal murder, but Bruce’s stare dragged him back

Bruce exhaled slowly, his brows furrowing deeper. “Children may see things as more than they actually are,” he said in a tone that made Jason feel like a high-schooler caught sneaking out, “but they’re also highly perceptive.”

“You’d rather I elope or something?” Jason asked, sass dripping in his voice as he placed a hand on his hip. Dick, who had just entered the room, was proud—stifling a snort.

Bruce stayed silent, unmoving and unamused.

Thankfully, Roy finally found his voice. He stepped forward, shoulders squared. “It’s my fault,” he croaked under Bruce’s withering stare. “I’ve always been beating around the bush. Jason had to beat me to confessing—hell, even my daughter beat me to asking for Jason’s hand in marriage.”

Jason groaned audibly, pinching the bridge of his nose. “Not helping, Roy.”

Bruce’s expression softened, just a fraction. A faint flicker of amusement—or perhaps grudging acceptance—crossed his face. Jason swore he saw it. He wasn’t going to admit it, but Jason could tell Bruce liked the idea of being Lian’s grandpa... or, knowing Bruce, her godfather.

 And he was going to fight Oliver over that title.

“I’m not saying no,” Bruce said finally, his tone measured, as if he were formulating new contingency plans. “But I need to evaluate this situation.”

Jason blinked. “Evaluate? What, you gonna run a background check on Roy? Because I can save you the trouble—he fails.”

Roy shot him a glare. “Thanks, babe. That’s helpful.”

Bruce didn’t respond. He simply returned to working on a new case. “Dinner,” he said over his shoulder. “Bring Lian. I want to hear this... marriage pitch.”

From the corner of the cave, Dick burst out laughing, finally losing the battle to contain himself. “I don’t know what’s better—B’s murderous intent or Lian’s proposal. This is gold.”

Jason sighed, running a hand through his hair. “I need a drink.”

“You need a ring,” Dick quipped, earning himself another middle finger from Jason.

Before Dick could make a snarky remark, Alfred entered the room, clearing his throat with a dignified cough. “Sirs, I am here to inform you that Oliver Queen is currently waiting in the living room.”

“Fuck! ” Roy exploded, marching toward the living room, absolutely livid.

Jason snorted, arms crossed smugly. Oh, this is gonna be good. After all, Roy had been toying with him ever since the day they were at the restaurant with Lian. Jason fully intended to relish every second of Roy’s upcoming humiliation. They had the same brand of daddy issues, and this was Roy’s karmic reckoning.

“What brings you here?” Roy gritted out the moment he reached the living room, already fantasizing about smacking Oliver in his head.

Oliver, dressed like he was ready to host a billionaire yacht party, coughed awkwardly and adjusted his tone. “I heard...” He paused dramatically. “That you and Jason are getting married.”

Jason, leaning casually against the doorframe, cackled. “Oh yeah, Roy. Forgot to send your old man an invite?”

Roy pinched the bridge of his nose. “God dammit.

Roy must’ve wanted some privacy, even going as far as to drag Oliver outside to argue. It made Jason’s stomach turn with worry, he knew that Oliver wasn’t fond of him but would he really be against Roy marrying him?

Jason’s heart sank, a nasty, irrational thought creeping in. What if I’m just not worthy of Roy?

“Wait what the fuck am I thinking??”  Jason grunted, crossing his arms as he forced himself to snap out of his thoughts. “This marriage would only be for convenience. Nothing else! Nothing else…”

Anxiety gnawed at him anyway, despite his bravado. Unbeknownst to Jason, Bruce was studying him like a particularly troubling case file. The older man exhaled quietly, his expression unreadable.

Meanwhile, Jason’s internal spiral was cut short by the sudden return of Roy and Oliver—not even five minutes later. Roy looked visibly distressed, dragging his hand down his face, while Oliver strolled in like he'd just won a lottery.

“Marriage,” Oliver nodded. “Sounds good! And if I remember correctly, Lian doesn’t have a godfather yet.”

Bruce, who had remained stoic until that moment, narrowed his eyes. “She already does.” His tone was sharper than any of his Batarangs.

Jason blinked in disbelief. “How’d it go?” he asked Roy, nudging him. “I thought your old man hated my guts?”

Roy sighed, wrapping an arm around Jason’s shoulder like this was just another day. “Nah, turns out he’s just pissed that Lian broke the marriage news before we did. Guy’s got a weird complex about being left out.”

Jason raised an eyebrow. “So... he’s cool with me?”

Roy smirked and gestured across the room. “What do you think?”

Jason followed his gaze and nearly burst out laughing. Bruce and Oliver were locked in a heated argument, each gesturing wildly.

“I’m practically her father figure, Bruce!” Oliver fumed, jabbing a finger toward the ground like he was making a closing argument in court. “I’ve earned the godfather role!”

Bruce's voice was low and deadly, cutting through the chaos like a bullet. “You abandoned Roy on an island, Queen. You think that qualifies you as godfather material?”

“Oh, so emotionally neglecting your kids makes you a saint?” Oliver shot back, his tone dripping with righteous fury.

Roy shook his head. “This is gonna last all day.”

Jason snorted. “Should we let them duke it out or step in?”

“Nah,” Roy said, grinning as though Christmas had come early. “Let ‘em fight. I wanna see who wins.”

From the sidelines, Dick was holding a camcorder, looking like a kid who was seeing Godzilla vs. KingKong for the first time. His grin was so wide it looked like his face might split in half. “This is gold,” he whispered gleefully. “Gold.”

Jason squinted. “Is that a camcorder? Seriously?”

“Don’t question me,” Dick said, eyes gleaming.

Meanwhile, Bruce and Oliver had escalated from verbal sparring to full-on shoving, their perfectly tailored suits somehow still intact. Jason wasn't sure if he was witnessing a family drama or the start of a WWE  match. Either way, he was absolutely getting a copy from Dick.

Jason rolled his eyes but couldn't hide the warmth creeping into his chest. As dysfunctional as this situation was, it somehow felt... stable. Roy’s arm was still slung casually around his shoulder, and that simple gesture was enough to drown out every anxious thought Jason typically carried around.

He bit his cheek, trying not to read into it too much. "Love? Nah. Couldn't be that. I don't do that kind of shit. Definitely just... relief. Yeah, relief."

But the flicker of warmth in his chest refused to be dismissed.

“I gotta thank Lian for her chattiness when we get back,” Jason muttered, ignoring the gentle thrum of something dangerously close to happiness bubbling inside.

Roy grinned. “Yeah, kid’s a genius. Might’ve fast-tracked our plan, honestly.”

Jason narrowed his eyes. “Speaking of fast-tracking, how the hell did we even get here? What did you do while I was asleep?”

Roy’s grin faltered. He suddenly couldn’t meet Jason’s gaze. “Uh… so... about that…”

“What the fuck did you do?”

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