Work Text:
1 - The first time he tried proposing was in public.
In retrospect, proposing to his girlfriend in public was bound to be a disaster. Simon just didn’t realize it yet.
Agatha Danbury, his godmother, was hosting a fundraising event for the orphanage where she was the patron. Several of the richest members of the society were invited - his godmother’s way of gaining more donations than expected, knowing fully well that they would want to one-up each other when it comes to charitable acts.
Scanning the room, he can’t help but fidget, his usual cool and collected facade slipping ever-so-slightly. Daphne had mentioned earlier that she would be arriving soon with her mother. As he waited from the sidelines, he couldn't help glancing out at the gardens. The venue his godmother chose for the event had an exquisite garden, fairy lights dotting it out like twinkling stars - perfect for a proposal. Not to mention the fact that the garden had access to the parking area for a quick getaway so that they can celebrate in peace. Most especially, to avoid nosey guests.
“You seem to be in a rather unusual mood, fidgety.” Agatha Danbury in all her glory, wearing her signature dark red colors, remarked. Sidling next to him, her hands folded elegantly on her cane, and mirth glinting in her eyes. “One would assume you are up to something.”
There was an amused smile on her face as if telling him she knew what he was planning for tonight.
“Aunt Agatha,” He greeted, feigning innocence. “What are you talking about?”
“Don’t play dumb with me, boy,” Her finger poked at him with each word. “You forget I raised you. I know your quirks like the back of my hand.”
Simon gaped at his godmother contemplating whether or not to deny her accusation. Even if it was in fact true, he must have looked like a fish out of the water as he opened and closed his mouth, searching for the words to say. His godmother let out a hearty laugh, almost doubling over.
“I suggest you find your voice soon.” Her laughter dying down. Simon turned his attention towards where his godmother was pointing at. Daphne was near the entrance, along with her mother, exchanging pleasantries with a few of the guests. Her light blue dress shone under the light, making her look ethereal like an angel descended on earth. “Best of luck, my boy.”
With those words, he quickly made his way toward her. Daphne noticed him, her smile growing brighter, making him feel at ease for the first time the entire night. “Hi.”
“Hi,” He replied, placing a chaste kiss on her cheek before turning his attention toward her mother. “Mrs. Bridgerton, you look wonderful tonight.”
“Thank you and how many times have I told you to call me Violet?” The Bridgerton matriarch chided good-naturedly. They exchanged small talks for a while before Violet Bridgerton spotted his godmother, leaving them to go speak to her.
His arm found its way around Daphne’s waist. Holding her close to steady his resolve and just because he can. Leaning in close, he whispered so that only she can hear. “Do you want to go walk outside? The garden’s quite beautiful.”
“Planning on avoiding other people?” Daphne teased, a playful smirk marking her lips. Simon resisted the urge to lean down and kiss that smirk off her lips. “Oh look, there’s Nigel Berbrooke. You might want to say hello.”
“Daphne,” He groaned, holding her tighter. She was poking fun at him, knowing full well how much he detests interacting in social functions. Especially, towards people like Berbrooke.
She laughed, stepping out from his hold. She grabbed his hand, inclining her head towards the exit. “Well… let’s go.”
Smiling, he quickly leads the way through the throng of people in the ballroom. Narrowly avoiding guests that would latch unto them and bored them with mindless conversation.
Barely five steps out of the room, Simon heard the familiar shrill of Cressida Cowper calling for Daphne. Normally, he would just walk away not caring about the other person. But, knowing Daphne she’d stay and interact with them, too polite for her own good. Daphne would always chide him about his manners or his lack of. He would only smirk in return, knowing that she meant no harm as an amused smile would soon creep into her face.
“There you are. I’ve been looking for you,” Cressida said as she made her way toward them. “Simon, you look good.”
Simon rolled his eyes as Cressida practically purred at him. He could feel Daphne tense next to him, annoyed at Cressida’s blatant flirtation. No matter how many times they would declare that they are in love and has no plans of ever breaking up, Cressida never seems to get the hint and stop her flirtations.
“Cressida, what a beautiful dress.” Daphne greeted courteously. Simon itched to just drag Daphne away.
“Mama had the best seamstress make it.” Cressida looked down at Daphne up and down. “You should go to her sometime.”
Daphne’s smile was strained. “I…”
“Oh, the girls want to talk to you. You wouldn’t mind, right, Simon?” Cressida grabbed her hand, leading Daphne to a group of girls that looked like they were ready to pounce the minute someone paid them any mind. Cressida was unstoppable not letting Daphne or himself voice their disagreement. Simon watched as his girlfriend was dragged back inside, stunned at what just happened.
Daphne turned back to look at him, mouthing an apology before disappearing inside. He groaned, making his back inside the ballroom to look for something to drink.
He’ll try again tomorrow.
2 - An unexpected guest got in the way of his second attempt.
After a failed first attempt at his godmother’s event last night, Simon thought that a more private setting would do the trick. The complete opposite of the glamorous setting, maybe in the vicinity of their home, he can finally take their relationship to the next level.
It was a Sunday, a perfect day for staying in and lazing about. No work that needed their attention and no one would be bothering them. They even both turned off their phone to ensure complete peace and privacy.
It was the perfect opportunity.
After what happened last night, he can’t shake the feeling that this too will also end badly. Simon pushed the thoughts away, focusing on the fact that the velvet box is currently stashed between the couch cushions. Daphne’s currently curled up by his side, wearing one of his jumpers. Half-eaten Chinese take-outs littering the coffee table. The television playing some random rom-com movie. Daphne was commentating on the movie, her witty remarks making him chuckle. He was barely paying attention to the movie, all his attention was solely on her. He was waiting for the perfect opportunity to go down on one knee.
It was peaceful and Simon knew that no one would be bothering them today. No one would get in his way.
Daphne squealed beside him, clearly adoring how the male lead confessed his undying love to the main protagonist. It was admittedly cheesy, but it did provide Simon with the opportunity to go ahead with his plan. Carefully reaching for the engagement ring that was carefully hidden. Simon was gathering his words, preparing himself for what he was just about to do.
Just as he was about to open his mouth, a rapid and loud knock quickly broke the silence. They both quickly sat up, staring at each other, wondering who could that be. They weren’t expecting any company nor did they other any more food.
Before either of them could ask who it was, a male voice wafted in. “Daphne, it’s me! Open up!”
“Colin?” Daphne called out, quickly rushing to the door to open it. “What are you doing here?”
Ignoring his sister’s question, Collin made his way inside their flat. Throwing a quick greeting to Simon, who was still glued to his seat and fighting so hard to not let his annoyance show. Colin flopped down on one of the armchairs. “I need to talk to you, Daff.”
The soft click of the door was heard before Daphne sat back down next to Simon. She reached for the remote control turning off the television, ready to give all her attention to her brother. Colin was squirming in his seat, his eyes darting back between Daphne and Simon.
“Colin,” Daphne started before pausing, watching Colin reach for the uneaten dumplings and chew on them nervously. She shared a look with Simon, who only shrugged and leaned back on the couch. “What’s wrong?”
Colin hastily swallowed his food, wiping the corner of his mouth with his jacket sleeve. “You weren’t answering your phone so I had to go here.”
Simon almost spoke out of turn, almost telling the other Bridgerton that that was the whole point. Instead, he kept his mouth shut, allowing Daphne to deal with her brother.
“And I needed to talk to you because I don’t know what to do,” Colin rambled on, getting up from his seat to pace around the floor. He continued pacing which was honestly making Simon a bit dizzy. Daphne, ever the saint that she is, stayed quiet. She was patiently letting her older brother speak his mind.
“I think I’m in love with Penelope.” Colin declared after his rambling. Daphne was shocked and so was Simon.
“What?” Daphne gestured for her older brother to seat back down. “Tell me everything.”
“Last night, when I went to go pick Eloise up,” Colin said, making his way back to his seat. “Penelope was with her and I just…”
“I’ll go make some tea,” Simon sighed, placing a pensive kiss on Daphne's head before standing up. She smiled at him in thanks. Simon figured to just let the two Bridgerton talk, a talk that was going to be lengthy.
He could hear Daphne asking about the whole story with Colin jumping in to tell everything from the beginning as he made his to the kitchen to boil some water.
So much for the perfect opportunity.
3 - In his third attempt, nature was not on his side.
Daphne has always loved the outdoors. Having spent most of her childhood in the countryside, the outdoors always brought out the childish glint in her eyes and the lightness in her step. It was no countryside, but the park they are currently strolling through had the same effect. She adored the place ever since they found it. It was close enough to their apartment that they can go there anytime and quietly tucked in the city ensuring that it won’t be packed with other people. It was no wonder she quickly jumped at his idea for a stroll.
Walking through the park, holding her hand, and basking in her happiness. It was pure bliss. Surely a sign that his proposal would go well today. He had it all planned out. Once they reach the group of trees at the end of the path, he’ll get down on his knees. He even had a speech prepared. The box in his pocket felt heavier as each step brought them closer to their destination. He can’t help but pat it, making sure that it was there.
He half-listened as Daphne retold the latest trouble her youngest siblings have gotten themselves into. Apparently, Gregory and Hyacinth managed to create glitter bombs with Benedict being their first victim. He can’t help but laugh, picturing the whole scenario in his head.
The Bridgerton family was too much the first time he met them, especially as someone who did grow up in that kind of household. They were boisterous, something to be expected with eight children. They were all different yet they all fiercely love each other. Their home was warm and loud, filled with genuine laughter. Quite the opposite of what he grew up in - a home that was cold, quiet, and a father that was never there. Her family always made him feel welcome even before he and Daphne started dating. Theirs was a family that everyone would be lucky to have.
They were near the trees now. Daphne walks ahead, his steps slowing down as he gingerly grazed the box in his pocket. She was gorgeous underneath the trees, her hair being swept away and a small smile gracing her face.
“Daphne,” He called out softly, his hands grazing the box. Waiting for the right moment to take it out. She turned to him, her smile never leaving her face.
This was it.
“Daphne, I love you.” His voice was low, declaring his unwavering love for her.
“I love you, too.” She replied instantly, without any hesitation making his heart soar. He took a step closer, gathering his words to tell her how much she means the world to him. Ready to get down on one knee and dedicate his entire life, his very being, to make her happy and safe.
“I…” His words were cut short by the sudden downpour of rain. Daphne shrieked, as the cold rain hit her. Apparently, he forgot to take into consideration the weather for today. “Shit.”
“I think we should make a run for it.” She’s grinning at him, eyes ablaze with that glint he knows so well. Before he could even respond, she was running down the path, splashing in puddles and laughing. She stops in the middle of the empty pathway and turns to him. “You coming? Or do I have to get out of these wet clothes by myself?”
She’s teasing him and truth be told, Simon kind of likes it.
Then he’s running.
They’re running and laughing. It’s a bit childish but it's freeing. The rain soaks their clothes, tangles in their hair, and coats their skin. As they near their flat, they slow down, holding hands and shivering. They head up to their flat, huddled together for warmth.
Simon tried several times to unlock the door, his hand fumbling because all he can concentrate on is the way Daphne’s fingers have slipped under the hem of his clothes, brushing against the top of his jeans. He finally opens the door and pulls her in, dropping the keys haphazardly on the hardwood floor.
He stares at her intently as he moves towards her, backing her into the door. She slowly unzips his jacket as he leans in, lightly grazing his lips against hers. He plants kisses along her jaw and down her neck. Daphne moans softly, tugging his jacket off him before taking off her own. They subconsciously move toward the bedroom, leaving a trail of wet clothes behind.
He slowly pulls her shirt off, letting it fall to the floor. His fingers ghosted along her spine, chuckling as she shivered. She loops her fingers through belt loops in retaliation, drawing him even closer. He can’t help but groan in response. She slides her hands under his shirt, running her hands down his back. Simon briefly pulled back to take his shirt off, Daphne quickly pulling him down to her. Their lips were meddling together as they fall back on the bed, hands barely leaving each other.
It’s dark inside their room, the rain tapping the windows rhythmically. His jeans lay abandoned on the floor, with the engagement ring still in its pocket. The rain might have foiled his proposal but Simon couldn’t even be mad. Not when the rain is the reason for having Daphne this close to him and basking in her love.
Maybe next time.
4 - The fourth time he tried, he nearly lost the ring.
By the end of the night, he can finally say that Daphne Bridgerton is his fiancee.
Simon Basset sincerely hopes so. It’s been a few days after his third failed attempt at a proposal. He was currently on his way to pick up Daphne from her work. They had a dinner reservation to catch. He had it all planned out - a romantic, candle-lit dinner. Afterward, during a walk by the riverbank and under the stars he’d ask the question. It’s somewhat of a cliched way of proposing,
But honestly, after three failed attempts, he is sticking to the tried and tested method. Who was he to argue at this point?
Easing into the empty spot in front of the building, he parked his car and got out. Sending a quick text telling her he’s outside. He receives her reply a few seconds later, informing him that she’ll be done in a bit. Shoving his phone back into his pocket, he immediately took the blue velvet box out of his pocket. The ring was sitting in it, glimmering under the street lights. He can’t help but imagine Daphne finally wearing the ring on her finger.
“Simon!” Quickly shoving the box back into his pockets, he smiled as Daphne made her way toward him. “Sorry, I had to meet an annoying client.” She huffed, her frustration making itself known.
He chuckled in response, kissing her briefly. “It’s fine, shall we?”
Dinner went smoothly. So smoothly, in fact, that Simon has a good feeling about tonight. They were currently strolling down by the river. Daphne was wrapped up in his jacket, the gentle breeze blowing through.
So far, so good.
“Oh, Simon look!” Daphne squealed. Grabbing his arm in excitement before sprinting towards a small concession stand. She quickly chatted up the young girl manning the stand, selling all kinds of knick-knacks.
He turns his back, taking the box from his pocket. He can't help but smile picturing the ring on her hand. Simon was lost in his thoughts that he barely had time to register a group of people walking. One of whom accidentally bumped into him causing him to fumble with the box. Almost dropping it into the river.
Fortunately for him, he managed to grab the box before it fell into the river.
Unfortunately, he failed to calculate his momentum, making him lose balance and fall head-first unto the river.
Gasping for air, he could hear Daphne calling out to him. There were quite a number of people looking at him. Rising out of the water, Simon stuffed the box into his back pocket before Daphne reached him.
“Are you okay?”
“I’m okay.” She took off his jacket and draped it on him, muttering the need to get him home and out of his wet clothes. Fearing that he might get a cold.
“I can’t believe you fell into the river.” There was no mirth in her words, just her pure concern for him. She held his cheeks, desperate to give him some sort of warmth. “What happened?”
“Someone bumped into me, I lost my footing.” Sensing that she would be going on again with concern, he grabbed hold of one of her hands leaning into it. “Really I’m fine.”
“We should go home.” Daphne realized they have gathered a small group of spectators. She was pulling him back into his car and Simon let her, too cold to argue. Simon sighed as his plan failed. On the bright side, at least he didn’t lose the ring. He would have probably dove into the river to fetch the ring if it fell.
It was halfway back home that he realized that this incident would end up being reported by Whistledown. Groaning, he knows Daphne’s older brothers would never let him leave this down.
After all, he literally made quite a splash.
5 - In his fifth attempt, he almost ended up in jail.
Simon was honestly at his wit’s end.
He was in a foul mood. Four failed attempts! Failing once was fine, but four times is entirely unreasonable.
Who the hell fails at proposing four times? Apparently, him.
His foul mood was made worse by the problem he had to deal with at the law firm. Buried deep into work for days, leaving him no time to plan or at least think about how he’ll propose. He barely even had time for Daphne.
Luckily for him, his girlfriend was completely understanding - letting him rant about the problems plaguing him at work and providing him comfort when he had a bad day. Her gentle smile and soothing fingers never failed to bring a certain peace to him.
He was looking forward to spending time with her after work, looking forward to actually spending quality time with her. She suggested a new pub near her workplace that her co-workers have been raving about. Maybe at the end of the night, they’ll go for a drive and when the opportunity presents itself, he’ll be able to pull out the ring that’s currently stashed in his car’s glove compartment.
What he was not expecting to see was someone else flirting with Daphne. His Daphne.
Simon was not a possessive man.
Scratch that, he was possessive. He just never let his possessive side shine. He trusted Daphne and knows how much she loves him. He never had a reason to assert the fact that he was her boyfriend.
Until tonight. She was seated alone in the booth, waiting for him. He can’t help but twitch in anger as the man kept on invading Daphne’s personal space. He could tell that Daphne was already getting annoyed from telling the man off. He didn’t want to make a scene, didn’t want the night to be ruined because a random man could not take no for an answer. But, when the man got physical, grabbing Daphne’s arm to force her to stay put. Leaning down to try to kiss her.
All Simon could see was red.
With quick strides, he made his way toward them. Grabbing the man by his shoulder and pulling him off Daphne, practically throwing him down the floor.
“What the fuck?” The stranger cried out, staggering from the force of being pulled off. Simon chose to ignore him instead he focused on Daphne, her eyes wide with shock at what just happened. He delicately held her arm, which was starting to red from how hard the man grabbed it, gathering all his willpower to not tackle the man down. She whispered assurances that she was fine.
“Hey! I’m talking to you.” The asshole clearly doesn’t back down. Frustrated by the fact that Simon wasn't paying him any attention, the man grabbed Simon’s shoulder to turn him around before punching him square in the face.
“Simon!” Daphne yelled. Simon touched his lip, already feeling the blood seep through. He quickly tackled the man down, throwing punches. The fight was all a blur to Simon. All he could remember was the sting of his punches, the creams of the other people in the pub, and the sensation of someone trying to pull him away.
Currently, they were outside. The police trying to get the story of what just happened. Daphne was by his side, telling the police what happened inside. The other man was a few feet away from them talking to the other police and Simon could not stop glaring at him.
“He suddenly just attacked me!” The man declared pointing at him.
“I attacked you because you were harassing my girlfriend!” The policemen quickly got in between them sensing that this could escalate into another fight.
“Your name, asshole! I’m gonna sue your ass!”
“Be my guest, the name’s Simon Basset!” The man was stunned, turning pale the minute he uttered his name. No matter how much he hates his father, he knows that the Basset name holds a lot of power.
Several more minutes later, the policemen let them both off with a hefty fine and a stern warning. They were inside his car, the tension thick. Daphne was gently ceasing up the dried blood from his face.
“You shouldn’t have done that.” She muttered. “I can take care of myself.”
He winced as she cleaned the blood from a nasty spot. He’s going to be sporting quite a number of shiners tomorrow. “I know. I’m sorry.”
“We should go home so I can properly clean your wounds.” Placing a soft kiss on his cheek, careful not to hurt him. He only hummed in return before starting his car.
Simon sighed, this was not how he pictured the night to end.
+ 1 - When he finally manages to propose to a Bridgerton...
Simon never planned on getting wasted but after five failed attempts in proposing, the sight of Anthony Bridgerton by his office door, inviting him for a drink was truly welcomed. Every attempt he tried so far has ended up in disaster.
This was probably his karma for saying he’ll never marry.
He downed his third glass of whiskey as he miserably tried to listen to his friend’s problem.
“I swear, she’ll be the death of me!” He only managed to catch the last bit of Anthony’s rant before the man ordered another drink from the bartender. He barely managed to suppress his scoff. Anthony’s relationship with Siena was doomed from the start, everyone saw that. Countless fights, breakups, and makeups, it’s a disaster. Every time they had a fight, Anthony would drink which seems to happen once a week. Heck, it’s a miracle if they last two weeks without any incidents. Simon getting dragged into a bar on a Friday night was not a new thing.
Normally, Simon wouldn’t encourage such behavior, knowing full well that his friend would do something stupid or crazy or, God forbid, both. Gesturing to the bartender to get another drink.
“You’re eager to drink tonight. Rough day?”
“Rough weeks.” He murmured, reaching for his new drink.
“Wanna talk about it?” He looked at Anthony and pondered on whether or not he should tell his predicament.
“Well…”
Simon woke up with his head pounding, a testament to the number of drinks he consumed the night before. Thankfully, the curtains were still drawn shut, blocking out most of the sun’s rays. Groaning, he slowly sat up, taking in his surroundings.
It wasn’t his room. That was the first thing he realized. The light blue wallpaper was nothing like the grey of his own room. The second thing he realized is that he’s still wearing his clothes from last night. Minus his jacket and tie, which were neatly folded at the bedside table.
The third thing he noticed was Anthony sprawled on the floor, the blanket tangled up with his legs. He must have fallen off in the middle of the night. His friend was drooling on the hardwood floor and like him, still in his outfit from last night.
“Anthony,” Nudging the man with his foot to wake him up.
His friend groaned in response, attempting to swat his foot away. Simon sighed, nudging his friend harder. “Anthony, get up.”
Anthony opened his eyes, winching a bit as he got up from the floor. “What happened?”
Simon could only shrug in response. He did not have any recollection as to what they did last tonight or even have the faintest idea as to how they ended here. They both gathered themselves, making themselves somewhat presentable as they made their way downstairs to the kitchen.
Thankfully, Violet Bridgerton was nowhere in sight. Unfortunately, Benedict and Colin were both downstairs waiting for them, sharing a look.
“Good morning,” Benedict greeted in a sing-song manner from the stool he was perched in, a steaming cup of tea in front of him.
“I’m guessing both of you know what happened last night?” Anthony asked his brothers as he poured two cups of coffee, passing one to Simon who took it gratefully.
“Look at them, acting like an old married couple.” Colin chirped next to Benedict, leaning on the kitchen island. Colin was trying to keep a straight face but failing to do so. The young man burst into a fit of laughter, Benedict quickly following him. Simon shot them both a confused look, clearly missing the joke.
“Can you two just tell us what happened?” Anthony cried out, annoyed at his two brothers. It took a while for the two to calm down but every now and then they would giggle.
“So, last night we came to pick you up.” Benedict started. “We got to the bar and well…”
“I think it's better if we just show them,” Colin interrupted, placing his phone on the island. Simon and Anthony quickly huddled next to each other. On the phone was a video of them, intoxicated. They were swaying and drunkenly singing their old university’s alma mater song.
Anthony let out a frustrated sigh, “So, we embarrassed ourselves last night.”
“Not only that brother, dear.” Colin replied, swiping to the next video. It was shaky due to the fact that Colin was snickering as he took it.
The moment Simon watched the next video, he just wanted the ground to swallow him whole.
It was him and Anthony out on the streets, acting all mushy and touchy. But that wasn’t the worse part. The worse part that was captured for anyone to see was him down on his knee, dramatically proposing to his friend. Anthony, for his part, was screaming yes.
Simon cringed, closing his eyes. He could hear Anthony groan beside him. Benedict and Colin started laughing again, throwing in congratulations and when’s the wedding between their peals of laughter.
This went on for a while, only stopping when Daphne with a pastry box in her hand walked in. “Morning.”
“Daff...” Simon sighed out of relief. Daphne only looked at him, with a smile on her face that tells him she has already seen the videos. Oh no.
“How are the lovebirds?” Daphne asked, placing the box down on the island. Colin and Benedict burst into laughter again. Anthony groaned, his head falling into his hands. “Can’t believe my own brother stole my boyfriend.”
She was teasing them.
“That proposal was supposed to be for you,” Simon confessed. Ignoring the three other Bridgertons in the room.
“I know.” A soft smile gracing her face as she made her way to him. “So…”
“So?”
“Ask me now.” Simon was stunned for a second before smiling widely, wrapping his arms around her.
“Marry me?” He asked her softly.
She laughed, pulling back a bit before wrapping her arms around his shoulders. “Yes.”
The second she finished uttering those words, Simon leaned in kissing her passionately. He can hear her brothers howling congratulations in the back. They stayed wrapped up in each other's arms as her mother and other siblings made their way to the kitchen after hearing all the commotion. It didn’t take a genius to guess what just happened. He could hear the rest of the joining in. He leaned his forehead against hers, softly telling her that there was a ring ready for her. That he’ll place it in her finger once they get back home. She only laughed in return.
It might not have been the proposal he had in mind. It took a while and a lot of struggles but this proposal was perfect. They were surrounded by the people that matter the most and after five failed attempts, he finally managed to do it.
He finally gets to marry Daphne.
Finally.