Work Text:
Donatello had wanted to tell you for a while, he wanted to confess his admiration for you, his need to be with you, his love for you. He's, of course, tried multiple times to confess to you, but every time something or more usually some one interrupts the delicate atmosphere around you both. The constant disruptions to his carefully devised plans took a toll on him, he was constantly trying to get a moment alone with you, sometimes sounding like a mad man when he'd drag you to his lab as soon as you had stepped foot into the lair.
Donnie dragged his legs to his bed, sitting there with his mask hanging low on his neck. He gazed at his phone flicking through old pictures of you and the guys hanging out together, his thumb stalled on one of the pictures. It was a selfie of you and him cuddled together in Central Park, the autumn leaves falling softly around you and your scarfs were pulled up to your chins. He smiled at the photo, the memory of your hair blowing in the cool breeze and your excitement when he brought you a hot chocolate from one of the street vendors. He remembered thinking, no not thinking... Knowing , that was the day he started falling for you.
He finally lied back in bed staring up at the high ceilings thinking back to the times he's tried confessing to you, all his failed attempts and yet you were somehow still friends with him. Friends . He felt like that was the only thing he'd be to you.
February 2019
Valentine's day was just around the corner and with the constant emphasis from the media of having a partner to celebrate this special day with the boys felt more alone than usual. Sure, they had their friends: April and (Y/N) but it wasn't the same as having a lover. They all took it differently, Mikey would gush about all the creative acts people did to impress their significant others and dream of creating the most heartwarming valentine's day card ever. Raph would sit in the projector room late at night and watch all the crappy romcoms he could find, a box of tissues and chocolate by his side as he blew his nose into the tissue crying his eyes out at the scene in front of him. Leo would constantly make fun of the way people walked around like they'd been shot by cupid himself, gagging at the romantic acts he saw around New York and Raph's movies. And then there was Donnie, he'd sit in his lab coming up with a plan to woo (Y/N) and somehow convey his feelings to them.
He'd never go to his brothers about it they'd only make fun of his over-thinking nature, to everyone else it seemed pretty clear that (Y/N) had a thing for the purple-clad turtle and even when told this by others he pushed it aside and said they were only trying to make him feel better. He had called April on the eve of Valentine's day her gruff voice moaning at him.
"Oooh boy, this better be good, do you know what time it is?"
"I know and I'm sorry but I've been losing my mind and I need your hmm" Donnie mumbled the last bit, looking down at his desk covered with glitter and craft paper he stole from Mikey's room. "What was that?" April asked he could her the snarkiness in her tone, he released a loud sigh "I need your hmmm." April laughed down the phone "Sorry D but I can't hear you, you'll need to say it agai-"
"HELP! I NEED YOUR help," Donnie calmed his voice down afraid he'd wake his brothers and father. "Sure D I'll help you, I'll be over in the morning." He smiled this is why April was his best friend "Thanks April." Her hushed voice came from the other side of the phone "No Problem Donnie, now get some sleep." He yawned in response "Yeah maybe you're right."
"I know."
Valentine's Day
April and Donnie had spent the whole morning decorating the garage for his little confession with (Y/N). Fairy lights littered the walls, while cut-out hearts were pinned randomly around the room, smooth jazz was playing from a speaker in the turtle tank. The pair stood back, hands-on-hips, taking in the sight of the totally transformed garage; now they just had to wait for you to arrive.
A few hours later you came bounding into the lair with valentine's cards for all the turtle brothers, they graciously accepted and thanked you. Donatello was just opening his mouth to ask you to follow him so he could set the plan in motion but someone had beat him to it.
"Hey (Y/N), come to the kitchen we just ordered some fresh pizza!" Mikey yelled from presumably the kitchen, Donnie watched as your form retreated with the others. His anger started to bubble but he sucked in a deep breathe "It's okay, it's fine just a little road hump but it's fine." He whispered to himself following the noise to the kitchen.
As the night went on Donnie had tried multiple times to drag your attention away from the others, he'd call your name multiple times but it only fell on death ears as you and Leo had a dance battle in the arcade. He would try dragging you by your arm only for Raph to pick the both of you up and carry you to the projector room to watch a movie, no matter what he did somehow his brothers always seemed to unintentionally ruin his plans.
April 2019
It had been a few months since his last attempt to confess to you but Donnie was still determined to show you his true feelings. He thought he'd hit jackpot when his three brothers told him they were going out for the night to watch some sports game. Perfect , a chance for you and Donnie to sit in the lair... Alone ... The perfect chance to confess to you.
He had invited you over with the claim you were going to have a marathon of Lou Jitsu movies. You arrived bag full of sweet treats, parking your ass on a beanbag chair close to Donnie your eyes widened as you watched the screen. An hour into the movie Donnie thought he'd try a move he saw in one of Raph's romance movies, he yawned really loud stretching his long limbs out and it just so happened that one of his arms settled around your back. Donnie kept his eyes on the screen but kept flicking his attention back to you gauging your reaction. You blushed a little but snuggled into Donatello's side and a small smile on his face.
"AW isn't that adorable." The sudden voice shocked the awkward teens, Donnie's arm flew from your back and slapped to his side. Donnie stood to attention facing the voice, your eyes wide and face blushing red.
"DAD!" Donnie yelled, Splinter hobbled around the couch and planted his ass onto it releasing a sigh "Oh don't mind me kids, I'm just here to watch this Lou Jitsu marathon." He held a smirk as he stroked his whiskers eyeing his son, Donatello started sweating profusely "I-I thought no one was going to be in the lair tonight." He somewhat gritted through his clenched teeth. Splinter threw his arms in the air, hands gesturing to the projector screen "And miss a Lou Jitsu marathon? I don't think so purple."
The rest of the night Donnie made sure there was a small gap between you both while his father snored loudly above them, you kept sneaking glances at Donnie he seemed pretty mad as his long limbs were curled in on himself, his arms crossed over his plastron, a pout gracing his lips.
August 2019
Summer break had just begun meaning you and April could spend more time down in the lair with the turtles. Today you had planned to head to a secluded beach where the guys didn't have to wear thick hoodies and pass out due to heatstroke. Leo, Raph and Mikey made a bee-line for the sea along with April, Splinter had set up shop under an umbrella his snores slightly disrupting the peaceful environment. You had just layed down your towel while Donnie continued to explain to you how the ocean is one of the most dangerous places in the world. Hearing him speak about something that actually interested him was a nice change than just hearing about yoki and mutants. In the time they sat together Donnie couldn't help but think that now was the perfect time to confess to you, he could see his brothers and April in the sea and it seemed they weren't planning on coming to land anytime soon and Splinter was knocked out.
He turned to face you, your eyes stuck in the book you were reading. He lovingly sighs and began to think of what to say. Should I just straight up say I like you? No that's to forward you should build-up to it. How about, I don't want to be friends anymore I'd rather be- no that's awful, ugh why is this soooo harddd. I see you like reading, you should read me someday- ugh now I just sound like Leo. Just keep it simple Donnie, just ask them if they want to hang out some time like a date. Okay, perfect that's it. Ask them on a date.
"Hey (Y/N) I was wondering if-" He turned to see an empty space beside him where his crush had once resided, looking around panicked he lifted the towel off of the sand and looked below it, of course, they're not under the towel idiot! Examing the dumb-dumbs in the sea his eyes landed on you on top of Leo's shoulders playing chicken with April on Raph's shoulder while Mikey referees.
December 2019
Snow had settled over the rooftops of New York, Christmas songs could be heard playing from the radios of the oncoming traffic, mouthwatering smells coasted through the night air. It was Christmas Eve and the turtles were all wearing festive jumpers that Raph had knitted, sure Mikey's had an extra arm-hole but it was the thought that counts. April and (Y/N) were able to join them for a short while, dancing along to their make-shift Christmas party. April had told the guys about Donnie's attempts to seduce you and all the times he's failed, Leo of course laughed at the pathetic attempts his twin made "I don't get it, why didn't he just tell us what he was planning?" Mikey asked.
Meanwhile, Leo was still laughing in the background lying on his shell, legs kicking in the air. Raph looked over to Leo then back to Mikey "I think he had his reasons." April snapped her fingers trying to get their attention "Guys, listen. We need to help Donnie, it is partially our fault he hasn't been able to confess." A lightbulb appeared over Mikey's head "I got it!" He clicked his fingers and dashed to the opened box of Christmas decorations, after rummaging around for a few minutes he pulled out a withered piece of holly. Leo looked up at him, wiping a tear from his eye "You're going to romance them with a dead plant? Miguel this is your greatest idea yet!"
"It's not just a DEAD PLANT Leon, its mistletoe," Mikey stated matter-of-factly, April's eyes widened "Whatever c'mon we gotta put that thing somewhere, then we lure the both of them under it!" April placed her hand in the middle of their small circle, each turtle placed a hand in too "3, 2, 1, Get D and (Y/N) together!"
"Mistletoe!"
"Romance!"
"For Donnie's honour!"
April pulled a hand down her face "We should have practised what we were going to say."
With April and Leo
Donnie seemed constantly stressed, for days he would just sit in the lab working away to the obnoxiously loud techno beats. While you were at the lair he'd try to make an effort to seem happy and relaxed but as soon as you'd leave he'd be back to his isolated self. Leo and April strolled into the lab seeing Donnie's hunched over form tinkering on some random piece of tech. Leo stood behind Donnie, pulling his chair out along with his brother, Donnie turned to face Leo with a stern look "I'm not in the mood Leonard."
"Oh c'mon Donnie, we're here to help you~" Leo replied sweetly, Donnie shoved Leo back with his hand on his face "Yeah right, when have you ever tried to actively help me?"
"Gasp! Donnie, I am offended you'd think that of me, your twin brother!" Leo feigned hurt Donnie grumbled under his breath turning back to his work "Stop calling us that!" April watched the brother's interaction from the entrance trying to think of a way to outsmart D. "Hey D, could you come help us with the projector? It kind of stopped working when Raph knocked into it." Donnie released a guttural sigh and dragged himself from his desk. "Oh, so he'll listen to you but not his dear twin brother. Typical." Leo grumbled.
With Raph
Raph stood in the doorway of the projector room looking over at your occupied form, he was freaking out on the inside, he knew you were smart and would easily see through his lies. He lingered there for a minute coming up with an amazing excuse.
"Hey (Y/N), can you follow me and Mikey for a sec?"
"Erm sure, what for?" You asked moving yourself off of the beanbag, Raph started sweating "Er, erm. Because I asked nicely?" You chuckled and shook your shoulders "You got me there." He breathed a sigh of relief that was easier than I thought.
Raph had led you to the kitchen entrance and stood cautiously by the door, Mikey had joined him with a small step ladder under his arms. You laughed a little "Okay guys, what's going on?" The brothers unintentionally looked up towards the ceiling, you followed their gaze and saw a dried holly plant or at least what was left of it.
"Is that-" You were interrupted by the sound of angst. Leo and April came into the kitchen through the other entrance dragging Donnie with them, shoving him into you roughly. The group quickly made their exit while you and Donatello both stared deeply into each other's eyes, Donnie seemed to suddenly realise where he was and pushed away from you coughing awkwardly. "Sorry about my family, I didn't think I'd have to apologise for them now but here we are."
You chuckled lightly and waltzed back up to Donnie placing your hands around his neck, his arms automatically swivelled around your hips your blushes rivalling Raph's mask. "It's okay, they have good intentions." You joked. Donnie looked confused until you pointed up to the dying mistletoe swaying in the airconditioned breeze, Donnie's mouth formed an 'O' shape. You both began to lean in, gradually getting closer you couldn't wait to have the feeling of his lips finally on yours. Just as your lips were about to touch your phone's ringtone blared through the quiet atmosphere, you both separated your heart thumping in your chest.
Quickly answering the call you sent Donnie a 'sorry' look, Donnie stared at you as you wandered around the kitchen talking to your mum a worried look on your face. I can't believe we nearly kissed, I was so close. Stupid technology! "Hey D," You asked, he looked up from the floor a gentle hum leaving his lips a blush still apparent on his cheeks. You looked nervous "I have to go home now, my mum wants me back before it gets too late." Donnie swallowed the lump in his throat and approached you "Th-that's fine, I-I can take you back if you want?" You nodded at him a smile adorning your face "I'd like that, thanks."
Back to the present
Donnie cringed at the memories of all his failed attempts, god he was so dumb not as bad as his brothers but close. Squinting his eyes shut he continued to think about that night, even though the set up by his family failed miserably the fond memory of the walk back brought a blush to his cheeks.
December 2019
Donnie had grabbed Sheldon and held you close to his plastron as he flew to your apartment, you remember blushing madly when he had suddenly swept you off of your feet; he thought your little squeal was adorable. Dropping you off at your bedroom window Donnie hung around for a bit just floating outside the window frame, a dopey look on his face. The moonlight up his figure as he hovered over your window, smiling deeply at you. Sheldon must have been complaining about the weight of the turtle on top of him but overall he didn't seem to mind too much.
It was now or never Donnie thought.
"(Y/N) I've been wanting to tell you, no, trying to tell you something for over a year now," he had started, his eyes boring into your own, a look of want reflecting in them. You slumped your arm on the window sill and gazed back up at him "Go ahead D, I'm all ears."
"Okay, well I-I-" he started to mumble and stutter, Sheldon had clearly had enough of the timid turtle's behaviour over the past year and decided to take the situation into his own rotors. Moving forwards Donnie's lips crashed onto (Y/N)'s. The two stared wide-eyed at each other not sure what to do, but as (Y/N) started to close their eyes and relax into the kiss Donnie too started to get comfortable, he placed his hands on their shoulders to steady himself better while they wrapped theirs around his neck.
Pulling apart the two stared at each other with rosy cheeks, "Well that happened" Donnie stated (Y/N) just chuckled and replied with a soft "Yeah." Donnie scratched his neck out of anxiety as he chose his next words carefully.
"Trust me you would not believe how long I've wanted to do that for" he joked, you held his hand and rubbed your thumb over his palm. You both stared at your intertwined hands as you spoke: "I think I could guess." You smiled warmly at him.
He looked past his shoulder at all the dark, empty streets behind him and sighed "I should be getting back," Donnie turned away from your window, Sheldon wavering slowly. Donnie's eyes widened as he turned back to you quickly remembering something he's been dying to ask you "Oh, by the way, would you like to go out next Saturday?"
"Absolutely" You swooned. "Great it's a date." Sheldon started to fly away taking the pair back to the lair where Donnie would no doubt brag to his brothers about his kiss.
"I've got a date! A date Sheldon! Oh, this is amazing."