How To Break The Heartbreaker
Daveed Diggs x Reader
Warnings: kinda gets spicy, but eh nothing to bad. swearing probably somewhere
Authors Note: sorry this isn’t a request, but I had this title awhile ago and out of me sprung this word vomit. enjoy.
The plan was set, the choices pre-made. The only thing left was to put this plan into action.
You’d checked and re-checked for errors or flaws in your plan, and made backup plan after backup plan.
The only problem?
You never thought of the possibility that you’d fall in love with the heartbreaker.
Known mostly as the Heartbreaker.
He had the most perfect body, the curly hair, and the bright smile. The only problem? He lacked commitment.
Girl after girl, he never settled. He got bored, broke her heart, and was onto the next.
He never reused old ways, he found new ways to shatter girl’s hearts and ruin their love life, at least for awhile.
He made them fall helplessly in love with them, and then?
Well, onto the next.
You absolutely despised Daveed Diggs, but couldn’t help but let him catch your eye every once in awhile.
How could you not? He was quite perfect, there was no denying that.
Until he broke your friend’s heart, you tolerated his acts of immatureness and turned the other cheek.
Step #1: Catch his eye
The make or break of the plan. If you couldn’t catch his eye, the plan was useless.
You stood in front of your closet, willing for your inner fashion diva to come forth and find the perfect outfit. To no avail, she stayed hidden inside you, and you were left to your own devices.
To catch his eye, you needed something that caught your eye…
Your eyes stopped on a black shirt, the string crossover in the front showing more skin than you were used to, but you knew that you’d be turning heads with this shirt. You slipped it on, along with your signature tight leggings. And shoes…?
Being as short as you were, you needed to be able to be seen. And for that to happen…
Heels it was.
Stepping into school that day was a sight to see, with your heels clicking the floor as you made your way past a gaping Diggs. You kept your demeanor cool, but on the inside, your heart was shooting out of your chest.
Phase 1 completed.
Step #2: Talk to him
Absolutely not what you had on your mind when you had woken up this morning, but you weren’t going to break his heart without any sort of conversation.
Fortunately for you, people followed like lemmings as you walked around that afternoon, and Diggs was bound to steal the spotlight somehow.
Much to your gratitude, you saw in your peripheral vision the approaching shadow of him, and you willed your awkwardness away and let your much cooler alter ego take over.
You shut your locker and turned around, finding yourself almost getting lost in the sea of brown that his eyes housed. You willed your heart to relax and smiled, leaning against your locker to assume a more relaxed stance.
You saw his muscles tense, maybe because the girls were always the ones fawning over him.
“I don’t seem to know your name. Do you have one, or can I call you mine?”
You fought the urge to roll your eyes and scream. The classic pickup line, he’d used it on every girl that he talked to. And weirdly, it worked every time.
“It’s actually Y/N, but to get that other title, you’ll have to work for it.”
You pushed off the locker, and made your way down the hall, praying that you had done the right thing and that Diggs would try again tomorrow.
Phase 2 completed.
Step #3: a gesture
This wasn’t something you could control, it was something that you prayed and hoped all night that Diggs would get the message to do.
Your friend had said that he always made some kind of gesture when talking to girls, and you weren’t sure what to expect, but a locker full of roses sure wasn’t one.
When you arrived at school the next morning, made up and dressed to impress yet again, there were quite a few eyes on you as you walked down the hallway, and you could feel Diggs’s eyes boring into your back as you opened your locker to reveal a huge array of multi-colored roses, but predominantly, red.
You fought the urge, once again, to roll your eyes. Roses, and on display for all to see. The gesture was sweet, but it was so public that it didn’t feel genuine. The sickening smell of the perfumed roses was starting to nauseate you, so you turned to Diggs and smirked.
His expression was hard to read, and you settled for a look that read satisfied.
You weren’t looking for satisfied.
So, you closed your locker and went on your way, much to the confusion of Diggs.
Phase 3? Completed.
Step 4: make him find you
You hated not being able to control this part of the plan, but you had to leave it up to fate that Daveed Diggs wanted you enough that he had to come find you. You didn’t expect it to happen so quickly, but when it did, you couldn’t help but feel proud of yourself that you were growing on him so fast.
You had stayed after school for a couple minutes to talk to your friends about to upcoming choir concert, and the building had mostly cleared up by then.
The teachers were in a meeting room, so the hallway was eerily quiet as you advanced to your locker to get some books for homework that night.
You felt a hand touch your back, and you jumped out of your skin and flipped around.
“Relax, it’s just me.”
You clutched your chest, and willed your breathing to slow down.
“Sorry for scaring you. I just wanted to talk to you for a bit.”
You nodded, feeling much like the professional plan maker in that moment.
He started, expecting you to say something. When you didn’t, he filled the silence.
“So, Y/N, why have I never noticed you before?”
He drawled out the syllables in your name, making you both surprised and smug that he had remembered your name.
“Maybe because I never wear something that makes you stare at my ass and boobs all day?”
His eyes drifted down when you spoke, and he cleared his throat as his eyes went back to meet yours.
“I suppose that could be a reason. But I regret not noticing you until now… Y/N, are you single?”
The question caught you off guard, because this part of the plan wasn’t supposed to happen quite yet.
“Mm. I’m not sure. I could be…”
You bit your lip, smirking.
“But you don’t have to know.”
You slid under his arm, and out of the school, breathing a sigh of relief as sunlight and fresh air greeted you as you began your walk home.
Phase 4 was complete.
Step 5: tease him
How in the hell does somehow who’s never been kissed before TEASE a man who’s broken half of the girls in your school’s hearts?
You wracked your brain for ideas, and went to your friends as well. They were as lost as you were, until your friend brought up some useful information.
“He really likes the color red. Could that help you at all? He’s having a party tomorrow night, and he’s inviting everyone in the grade. Are you gonna go?”
You thanked your lucky stars of the convenient timing of the party, and set to work on how to tease Diggs.
You arrived at school the next day in a tight, white v-neck shirt, ripped maroon pants, and a flannel tied around your waist, making this day the laziest of them all, and still somehow, Diggs followed your every move with his eyes.
He approached you as you were waking to lunch, cornering you.
“Hey. So tonight, I’m having a party at my place. I’m inviting the class, but I wanted to make sure you’d be there.”
You smirked, and raised your eyebrows.
“Yeah I’ll be there, but only if…”
You pushed closer to him, and his eyes darted to your lips.
You quickly backed away.
“…my friends can come too.”
You finished, successfully leaving him flushed.
“Oh, yeah. Yeah they can come too.”
“Great, see you tonight then.”
You pushed past him and walked to lunch, in a trance-like state. You just teased Daveed Diggs into thinking you were going to kiss him. That was just part of the plan, because tonight was the real deal.
When you arrived at Diggs’s house, the loud music was already pulsing throughout the street, and you winced as you struggled through the throng of people in your long black heels.
Your short maroon dress was making it more difficult to maneuver around the room, but you had to make sure that Diggs would notice you tonight.
Luckily, his eyes caught yours as soon as he saw you, and he made his way over.
His voice was a bit rugged, and you pushed away any thoughts of sexiness that were brought immediately to mind.
His eyes scanned your body.
“You look good tonight.”
“Thank you. I wasn’t sure about the red, do you like it?”
You spun for him, and he bit his lip to suppress a comment on how much it turned him on.
“I-I like it. It suites you.”
You smiled as he blushed.
“You don’t look to bad yourself.”
You put a hand on his chest, and he put a hand on your waist.
“Yeah, well I try sometimes.”
You laughed, and removed your hand from his chest.
“Well, I’m going to go find my friends. Catch ya later.”
You walked away, swishing your hips a bit more than usual, and when you glanced behind you, Diggs was staring with lust filled eyes.
Phase 5 was completed.
Step 6: get him to ask you out
Every time you thought about the next step in your plan, butterflies would fill your stomach until you crushed them, denying the fact that you were slowly falling for Daveed Diggs.
It wasn’t like it was a possibility; he was your friend’s ex, he was a renowned heartbreaker, and you were trying to break him, not fall in love with him.
Yet, it was a struggle to constantly ignore your feelings everyday when you saw him staring at you.
For 2 days nothing happened, and you were worried that you’d done something wrong. Was your whole plan ruined because Diggs’s couldn’t keep it in his pants?
Thankfully, on a Friday afternoon, you saw Diggs coming down the hallway, and straight towards the place where you were standing with your friend.
Your friend smirked.
“I see you have company. See ya later.”
She’s linked off, leaving him to fill her spot.
“Would you like to go-”
“-out on a date with you?”
You interrupted, half shocked that he still wanted you.
Did he want you? Yes.
Did you want him?
Phase 6 was considered accomplished.
Step 7: have him fall in love with you
The date had you stressing out, 1. Because it was in a super fancy restaurant and 2. Because Diggs would be there, all alone, with you.
Not ideally what you had planned for a Saturday night, but you went along with it as you dressed in a dark red dress that hugged your curves and went down to your ankles. You had really went all out, with your red lipstick and curled hair, ready to walk out the door into Diggs’s car.
Unfortunately, your mother stopped you at the door and told you to invite him in.
Sighing, you grabbed your phone and texted Diggs, letting him know of your situation.
Seconds later, you heard a door slam and a doorbell ringing.
You opened the door to reveal a pretty (you hated to say this) handsome looking Daveed Diggs standing on your doorstep with a bunch of roses.
You smirked and invited him in. He handed you the roses, and leaned down to whisper in your ear,
“For old times sake.”
You smiled, and felt the butterflies returning, but this time you didn’t squish them back down.
Instead, you let them fly around your body.
Your mother came out from the kitchen, and her eyes widened when she saw Diggs.
“Well, Y/N. You have some magic left in you after all.”
You smacked your forehead as Diggs laughed and shook your mother’s hand.
“I’m Daveed Diggs, nice to meet you ma'am.”
God dammit. It would be 10 times harder to break his heart now that you learned he had manners.
Your mother was impressed with your date.
“Don’t stay out too late. And no funny business you two!”
She waggled her finger, laughing.
You turned bright red as Diggs wrapped an arm around your waist.
“Don’t worry Mrs. Y/L/N. I’ll have her back soon.”
Your mother stood waving on the porch as you drove off. You put your head in your hands and groaned. Diggs laughed and patted your back.
“Sorry about her. Always looking to embarrass me.”
He stopped at a stoplight, and turned towards you.
“I think it’s cute, how flustered you get. How your mom cares about you a lot.”
He smiled, but there was a sad look in his eyes, something that was hidden away.
Something you didn’t know about.
In that moment, you knew there was more to Daveed Diggs than what met the eye. Sure, he was a heartbreaker and the school player but…
There was something more there.
And you felt bad for judging him.
Once you reached the restaurant, Diggs got out of the car and raced to the other side to open it for you.
You smiled at him.
“Such a gentleman.”
He flushed, and you let him lead you inside.
Once seated, you were faced with an array of menu items, all of them so fancy sounding and so French sounding that you pronounced yourself incompetent of being able to order, and you placed the menu down.
Diggs peeped at you from over the menu, and laughed at the sight of you struggling to pronounce the French names.
“This place is kind of snobby. You want to just get out of here and get coffee?”
You immediately perked up at the mention of coffee.
“I’ll tell you what, Diggs, I’ll get coffee with you only if you promise me doughnuts.”
You reached across the table and shook on it, and then sprang up and ran out of the restaurant, leaving Diggs to laugh and promptly follow you.
You laughed all the way to the Doughnut Shoppe, a local place that you absolutely adored.
After ordering 2 cappuccinos and a dozen doughnuts, you settled at a table in the corner of the restaurant, and laughed at how out-of-place you and Diggs looked in your fancy attire.
You bit into a chocolate doughnut with M&Ms and groaned.
“I love this so much.”
What you didn’t know was the Diggs wanted to say the same thing, but about you. He admired you from across the table, how cute you looked with your hair in your face and a bit of chocolate on your lipstick.
Instead, he laughed and swiped the chocolate off your lips, leaving you a bit dazed and slightly giddy.
He loved the sight of you, laughing and smiling.
And without you knowing it, Phase 7 was complete.
Phase 8: break his heart
You couldn’t do it.
You could hardly stay away from Diggs now, and he was your every thought when you weren’t together.
You had gone on several more dates with him, each of them leaving you as lovestruck as the last.
Word around the school was that this was the longest Diggs had kept a relationship going, and with this gossip, your friends were pressuring you to break his heart.
“I mean, that’s the only reason you’re doing this plan, Y/N.”
Your friends all began to seriously doubt your belief in the plan, and you were doubting yourself as well.
“I can’t do it.”
Not to him.
After all this planning, after all these phases, you had never expected to fall for the heartbreaker.
And yet, you had.
Phase 8 was not completed. Not yet.