Hey-o! 20, stressed student, sporadic writer, and a closet fangirl. This is for all of my closeted fandom loves (Arrow/Olicity, Brooklyn Nine-Nine/Peraltiago are my main loves as of now). Everything else will be other fandoms or things I find too hilarious not to share. Welcome, feel free to hit me up with messages! xoxo
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The Best Worst Proposal
Fandom: Brooklyn Nine-Nine Pairing: Jake/Amy Rating: General/Teen (nothing explicit, or particularly mature. This is pure fluff) Disclaimer: Obviously I own none of the characters etc. Also, this is my first B99 fanfic, so beware (??). All mistakes are mine (feel free to point any out - I welcome constructive criticism/feedback).
Summary: It’s been a long week for Amy, and the last thing she expects is for Jake to pull an elaborate hoax to celebrate one of their anniversaries - and it’s not even an anniversary they’ve really celebrated before. But, because she loves him, she puts up with it (and in the end, it’s totally worth it).
Amy was exhausted after following up leads for almost a week concerning what seemed to be a low-level drug dealer. But after this many dead-ends, she couldn’t help but wonder if it was potentially more complex than she originally thought. Well, imagining that it was more complex was better than the alternative—that she missed something.
She entered the bullpen close to midnight, focused on how else she could approach the case. Case file in hand, she reread all available information. She just needed a new perspective, and potentially a new binder. She could organize all her leads and maybe she’d get that new perspective she needed.
“Five, four, three, two, one…”
Confused, Amy looked up to see Jake finish counting down before turning on celebratory music. Various members of the squad shot confetti into the air and began dancing in place with Jake before he slid forward on one knee. He only stopped when he was kneeling in front of her with a familiar red velvet jewelry box in his hand. It brought on an intense sense of déjà vu, but also made her heart stutter in anticipation.
Is this- could this be- no. He wouldn’t- her mind was struggling to process what was happening. All she could think was that her hair was probably a mess, and her makeup was probably smudged and everyone was looking at them, and Jake still wasn’t speaking. This was not how she had imagined (or planned) on being proposed to—if that was what this was! There was no evidence that Jake was proposing after three years of dating. Except the kneeling. And the ring box. And his smile. Oh God.
“Amy Santiago, you have made me the happiest man on earth for the past three years. I spent a liiiiiiiitle bit more than one whole dollar on this ring. In honor of our anniversary of the best worst date ever, will you go out with me again tomorrow? You have to say yes.” He paused, wrinkling his nose. “Except not really. Because you have equal say in this relationship. Obviously. And I know you’ve got that one case that just isn’t working out. But I checked your calendar before setting all this up. Whaddya say?”
Amy felt like laughing (and crying, but that wasn’t the point). Jake wasn’t proposing. She was so stupid. All that worrying (and excitement and giddiness, shut up) for nothing. He was just being a dork and trying to celebrate one of their anniversaries.
“Ames?”
“Oh! Of course. I can’t wait to celebrate the best worst date ever with you.” She says, unable to hold back the giggle at the back of her throat.
Jake looked at her a little oddly at the giggle before sliding the ring on her finger—her left ring finger, not that it was important.
“Promise to keep it on, Ames? This one took a few tries to get, and I’ll be crushed—nay, devastated—if you lose it.” He requested with a goofy grin, holding her hand tightly. The goofy grin though...was it a little strained at the edges?
Before Amy could examine it more closely, Jake’s face shifted into his normal dopey look. Accepting that the ring was part of whatever scheme he had brewing for their date (it brought to mind a few other dates he had planned that were met with only moderate success—like the roller-skating incident) Amy nodded. “Sure, babe.”
Finally getting up to both feet, Jake grinned enthusiastically. “Thanks. You’re the best Ames.”
“I know.” She shrugged her shoulders nonchalantly before grabbing her bag. “You ready to head home?”
“Yep. Just gotta put a few files away.” He waved three casefiles at her before jogging over to the records room. Amy contemplated following him (they’ve had some good times in that room) before deciding that it would require far too much energy. Falling into her chair, she began reorganizing her drawers while waiting.
She’s only made it through her top drawer when Jake reappeared. Putting on her coat and swinging her purse over her shoulder, she accepted Jake’s hand and waved goodbye to the rest of the squad.
With the familiarity of Jake’s conversation washing over her, the difficulty of her current case prodding the back of her mind and the exhaustion of a long day finally setting in, there was barely any room left in her mind to notice that the ring felt a little heavier than the one from five years ago.
Amy is nothing if not conscientious, but the ring that she told Jake she would keep on created some problems in her regular routines. She couldn’t shower with it, and had to remember to put it back on in the morning (after she had forgotten to put it on last night, after washing her face, Jake had complained—he was really serious about her keeping it on, for whatever reason). It got caught in her hair a few times as she ran her fingers through her hair after waking up, and it pulled at a loose thread in her pajama top as she was changing. But, Amy kept the ring on, because she told Jake she would (and Jake had put up with her and worn the matching sweaters she thought would be so cute on Thanksgiving. The least she could do was wear this stupid ring even if it made her heart beat a little funny).
She only had to tell two people that she wasn’t actually engaged. The first was her barista, Lauren. Lauren was their ‘regular’ barista, and Amy would almost consider her a friend. Almost. Upon seeing the ring, Lauren had squealed and attracted the attention of a few customers and her coworkers.
“Jake finally popped the question?” Lauren was grinning. “Lemme see that ring!”
Ignoring the embarrassment (God, it was so similar to the actual worst date, when she had been so goddam embarrassed in that horrible dress. Was that Jake’s plan all along? Because if it was, she had underestimated his planning ability) and everyone’s curious faces, Amy grinned ruefully. “No. He didn’t propose. This is just a gag – celebrating one of our anniversaries.”
Lauren looked crestfallen. “Really? Too bad, it looks like a nice ring – and it suits you.”
Except for the fact that it was plastic and cubic zirconia, Amy would have agreed. It could have been a tasteful round diamond bracketed by smaller baguette diamonds in a simple setting. Something she would have chosen for herself. But Amy knew better. “If only it weren’t plastic, right? Can I have our usual?”
“Sure thing. It’ll just take a second.” Lauren accepted the debit card and ran it before gesturing Amy to the side to wait.
The second person she tried to explain it to was a well-meaning older woman, also waiting for her drink.
“I don’t understand. You’ve got the boy, and the ring, but you aren’t engaged?”
“Yes. My boyfriend has an…interesting sense of humor. He likes to celebrate things a little differently. This is a joke.”
“What kind of joke is a fake engagement?”
“It’s not a fake engagement. We just…aren’t engaged.” Amy had to physically restrain herself from saying yet. “We’re only celebrating one of our anniversaries.”
“Hmph. I just don’t understand you young people.”
Before Amy could defend her generation of young people, the woman had gathered her tea and left.
After that, she just accepted the congratulations. It was easier. Also, only like two extra people offered congratulations.
Getting to the precinct, Charles took one look at her and giggled. Amy ignored him. He was probably just imagining that the ring was real (not unlike what she was doing), and was demonstrating his overinvestment in her and Jake’s relationship. Or he was in on whatever joke Jake had planned.
Surprisingly, a few of the perps around the bullpen and in the holding cell congratulated her (their frequent flyers - ones who remembered that Jake and Amy together. Amy tried to ignore how touched she was that they cared). Someone tried to steal the ring (she got to twist the dude’s arm up behind his back like she’d seen Rosa do before), and another gave her a lead on her drug case. After a late (late, late, really late) lunch, Jake texted her about their night. He and Rosa were on a stakeout for a string of B&Es they were working.
Wear something nice tonight. Idk when I’ll be back, so ill pick you up @ home @ 8
. . .
You mean you’re not going to choose my outfit this time?
. . .
Haha, Santiago. Not tonight. Unless you can finally admit that my fashion sense is superior
. . .
Never. You forget that I’ve seen you in a speedo.
. . .
And you loved every second of it. Gtg, think the perp is here. Love you!!!!
. . .
Love you too.
Putting her phone down, she couldn’t help but be distracted by the stupid ring again. It was remarkably shiny for a gumball machine ring and reflected surprisingly well in the precinct’s harsh fluorescent lighting (just like it did in the sunlight). Avoiding the potential daydreams that she had been succumbing to more and more frequently (that involved a real diamond ring and an intimate ceremony not unlike the one she had planned for Rosa those years back), Amy went back to her paperwork. If she finished up the paperwork and logged evidence efficiently, she may be able to clock out at a reasonable time so she wouldn’t look like a total troll tonight (those were Gina’s words. Amy had made a note to look it up on UrbanDictionary. Weren’t those troll dolls supposed to be kind of cute?).
Eight o’clock found her in a blue dress, waiting for Jake to pick her up from the apartment. She was feeling oddly nostalgic for their (best) worst date, and the horrendous dress Jake had chosen. Instead of the hideous monstrosity with bow, this blue dress was actually flattering, and didn’t make her feel like she was fourteen again (or make her feel like Jake’s second choice. What was so great about Jenny Gildenhorn, anyways?).
Six minutes later, a car horn honked. Then honked again. And again, prolonged this time.
“That idiot.” Amy muttered, locking the door behind her as she rushed down the stairs. Opening the outer door, she was met by Jake, standing by the car, preparing to honk again.
“Wow, Jake. You’re really taking this…reenactment kind of far, don’t you think?”
Jake grinned before jogging over to open the passenger door for her.
“When have I ever taken things too far?” He joked. Amy gives him her patented Really? Are you kidding me, Peralta? look. “At least I’m not wearing the shorts.” He defended before closing the door behind her. Amy had to admit that she’s glad he’s not wearing the shorts—though he did dress up with a coat and tie (Amy couldn’t help but think that it was sweet that he actually took the time to think about changing for tonight before he left for work in the morning). It’s a pleasant change from the regular plaid/hoodie/jacket combo he usually wears at work (although, to be honest, she’s found herself to be quite a fan of that look too).
Closing his own door behind him, he paused to lean over and kiss her lightly on the cheek before moving in for a more intimate kiss. She smiled into it, leaning towards him and angling her head to try and take control. He grunted lightly before giving in. Too quickly, he pulled back and gave her a peck on the lips.
“You look gorgeous, Ames. Definitely should have let you dress yourself the first time.”
“Aww, where would the fun in that be, though?”
Jake laughs. “You’re right. Definitely wouldn’t have been any fun.”
The drive was spent in comfortable conversation. Amy critiques Jake’s driving while he cracks jokes. Intermittently, they discuss a few of their open cases. Amy hasn’t brought up her troublesome one yet, wanting to let it sit in her mind a little longer before bringing it up to Jake. Without realizing it, she’s apparently developed the habit of spinning the ring around her finger. The habit only came to her attention when Jake reached out to hold her hand halfway through their drive (offhandedly, she thought about how it would be a bitch to quit the habit, once she took the ring off).
After they’ve parked, she realizes they’re at Shaw’s. “Just like the actual date?” She asked him, walking into the bar still holding Jake’s hand. All Jake could do was nod and grin (is that a bashful grin?) before they’re met by almost the entire precinct. The night started like any other night after work—drinks with the squad, stories about best/worst perps, teasing Boyle and a few harmless bets. It didn’t feel like anything special (not that it had to, Amy would spend time with Jake however she can). But it shifted when Jake asked her to dance.
She still wasn’t the best dancer (unlike Jake—though she still hadn’t learned where he gained that particular talent), but she has undoubtedly improved over the years. “I swear to God, Peralta, if you’re going to try and make me dance that jig from The Titanic, I will murder you in your sleep.” She threatened. It was still unclear how far Jake is going to take them down memory lane.
“Nah, not tonight. Figured we could just sway a bit. That’s something you can handle, right?”
Rolling her eyes, Amy purposely stepped on Jake’s foot. The bastard just laughed before unexpectedly forcing her into a turn. She betrayed herself by laughing. Their planned swaying quickly evolved (devolved? Amy’s not sure exactly how to classify it) into poorly executed dips and twirls. But she and Jake were laughing the whole time, and it never occurred to her to chastise him for being a goof. It’s part of why she loves him, after all. And really, it felt remarkably romantic.
By the time the crowd has changed over to the drunker and/or late night party types, they’re saying their goodbyes and putting on coats in preparation for, as Jake called it, ‘Part 2 of the most amazingly awful best worst date in the history of ever.’
Amy barely had time to complain about the length of his name before they’re stepping out of the car again. The neighborhood wasn’t the greatest and she couldn’t see anything that looked like a place you would take someone on a date. Suddenly, she realized exactly where they are.
“Oh my god, Jake. Seriously? The building from our stakeout?” Amy was a little ashamed that her voice comes out more affectionate than she had planned. This was not what she would call an occasion to dress nice.
“Gotta do this right.” Jake says. For a split second his face showed shock before morphing into a forced look of humor. “Even brought some peanuts, ‘cuz you know I get snacky.”
Amy rolled her eyes. “How are we supposed to get into the building?”
“Through the door. Duh.”
Confused, Amy watched as he unlocked the front door and gestured her through. The last time they were here after hours they had to sneak in. Walking up the stairs, Amy can’t help but wonder how Jake got a key—how much planning had he put into this (subpar, if she’s being honest) date? The only thing it really has going for it is Jake, who usually finds ways to make all her days better. While it’s been fun to reminisce, part of her would have rather just stayed in and watched Property Brothers or something.
On the roof, she sat on a crate, trying to ignore the goosebumps on her legs. She admired the view (it’s not that great, actually) and waits for Jake to join her. As he sat down, he draped a blanket over her lap, successfully covering her legs and keeping her warm. A bit of her vague irritation leaks away.
“Thanks, babe.” She murmured.
“No problem. I know how cold you get. Your feet are like freezer-burned popsicles in the morning.”
“Hey! I can’t help the temperature of my feet!” she replied in fake outrage—this wasn’t a new argument.
“Socks, Amy. Socks help to keep our tootsies all toasty warm.” Jake said. “Dammit, I ruined the serious vibe I had going on. But how I could I not say ‘tootsies’ or ‘toasty warm’?”
Seeing Jake’s genuinely concerned face, Amy couldn’t help but laugh. “If you hadn’t said either, I would have been concerned.”
Seeming to accept that, Jake nodded along before tossing a peanut up in the air and catching it neatly in his mouth. “Ready, Ames?”
“Hit me.”
They spent the next few minutes tossing peanuts back and forth. Amy noted, with a fair amount of pride, that she has definitely improved since their first night on this rooftop.
Jake, however, has been doing worse and worse as the night wears on.
“You okay, Peralta? Are my stupendous skill psyching you out?” She joked, trash-talking him as he missed yet another peanut.
His eyes, which had previously been rather glazed over, quickly refocused. He gave her a quick (and rather unconvincing) grin. “Yeah, your ‘volume is key’ strategy is really psyching me out, Santiago. Here, this’ll be a high one. Ready?”
Amy nodded. “Born ready.”
Jake tossed the peanut up in the air. Amy tilted her head back, trying to follow its path. She leans back a bit…almost there.
It bounced off her forehead.
“Dammit! Peralta, that ones on you, because that was a terrible throw!” She was laughing as she said it though, sitting up straight and getting ready to throw him a peanut (she’s thinking she’ll just chuck it in the air, see if he’ll run after it like the goober he is).
But, when she’s finally totally straightened up and has her eyes open (they’d been closed before, in laughter, she thinks), Jake was in front of her. Kneeling on one knee. And looking the most serious she has ever seen him.
Everything freezes.
“Oh.”
“Amy Santiago.” He grins. A genuine, god-i-love-you grin that reached his somewhat glassy eyes. Amy’s eyes were feeling a little glassy (i.e. wet) too, to be honest.
He continued, “I wasn’t lying when I said you’ve made me the happiest man on earth for the past three years. But, years ago we went on the best worst date ever and that was the moment that I realized what you could be to me—that you could be everything. And you are. I’ve been kind of obsessed with you since then, and I can only hope that you feel a little of the same,” Jake takes a deep breath before chuckling, “because I’d be honored if you would embark on the incredibly un-boring adventure of life together-”
Without her explicit permission, a choked little giggle-sob escapes Amy’s mouth. Jake ducks his head, and matches her with a wet-sounding chuckle.
“And continue to wear that ring for the rest of your life. Because it was definitely a little more expensive than the one I gave you almost five years ago. I’ve typed this speech up, revised it an practiced it a million times - Santiago style.” He winked. “So, Amy Santiago. Will you marry me?”
Amy never thought she would be one of those girls that cried when she was proposed to—she was too logical. Besides, she never thought she would be surprised by her proposal. It would be something she and her partner discussed and agreed on (more of a contract/mutual decision, her brain supplied). But here she was, crying.
But, Amy realized, she never expected to be partners with a man like Jake Peralta. Someone who pushed her and her buttons, who made her laugh and smile and made life always seem like an adventure. Someone who made her a better person, and drove her crazy in the best way possible despite (or because of) their differences.
“Uh, Ames? Should I stand up? Are you still thinking, or…?”
“Oh god.” She hadn’t answered. “Of course. Yes, I’ll marry you Jake. I would love to. Oh my god.”
Jake just laughed, lowering his head over where he had been gripping her left hand. “Thank god. I was starting to get a little worried.” He joked with her as he pulled her up to stand with him.
Amy could see in his eyes, though, that there had been a small part of him (the part of him that always reminded him that his dad left, and thought that he wasn’t worth her love. This was also the part that Amy endeavored every day to prove wrong) that had been worried.
“I love you. So much.” She reminded him.
“I love you, so much, too.” He responds before kissing her deeply.
Their first kiss as an engaged couple her brain reminded her. She smiled, giddy at the thought. Because she was kissing her fiance. And she was wearing an engagement ring-
Abruptly, she pulled away. Jake’s eyes popped open. “Not to complain, but you kind of ruined our moment there Santiago-”
“Are you telling me that I’ve been wearing an actual engagement ring for over 24 hours, thinking that it was a cheap vending machine ring?”
“Uh…maybe?”
“What if I had lost it? Or thrown it away because I thought it was stupid? Oh my god…”
“Well, then you would have plunged me back into crushing debt, babe. But you didn’t. Just like I knew you wouldn’t. Because you owe me after the Thanksgiving sweaters. But mostly because I know you still have the actual cheap plastic one in your jewelry box.”
Amy blushed. Because he was right—that stupid, scuffed, plastic ring was sitting in her jewelry box. She had retrieved it after their fake fight. And ever since then, it had been safely tucked away.
“Besides, this’ll make a great story to tell the kids. How their mom didn’t even realize it was the real engagement ring until a day later. Some detective you are.”
Amy punched him in the shoulder, ignoring his muttered ow. “Just because you’re my fiance doesn’t mean that I won’t still kick your ass.”
Instead of responding, Jake just grinned at her dopily.
“Jake?”
“You called me your fiance.”
Amy blushed before squaring her shoulders. “Well, you are my fiance. Besides, didn’t you just reference our unborn children? When did we discuss kids?”
It was Jake’s turn to blush. “I, uh, guess we didn’t. But, I kind of assumed…which I shouldn’t have. But, well. I want to. And I hope you do-”
Amy cut him off with a kiss. “I do too. We can talk numbers later. For now…let me just enjoy kissing my fiance.”
Jake grinned before obliging her.
Less than a minute later, he pulled away. “So, I was definitely going for a romantic vibe here, but whaddya say we move it inside?”
“Oh god yes, I’m so cold.”
“Plus, I figured a bed might be nice.”
“Ooooh, I like the way you think, babe.”
Jake winked at her playfully (it was a horrible wink – his entire face scrunched up) before gathering their stuff and grabbing her hand.
Laughing and kissing the whole way down the stairs they practically fell into the car. Amy spent the entire car ride with her left hand in Jake’s right. She could feel him stroking the ring and feel the metal heating up from their joined hands.
It was only later, lying in bed with Jake (this time he was absentmindedly stroking her back, with their fingers linked on his chest) that she realized she’ll never have to take the ring off. It will stay there forever, eventually joined by a second one—one that will match the ring he will eventually wear. She could keep spinning it around her finger forever.
She could go to the coffee shop tomorrow and show Lauren the ring for real, find that woman and tell her that the engagement is real. She could accept people’s congratulations because she really is getting married. To Jake Peralta. He’ll be her husband. And she’ll be his wife.
It was to those happy thoughts that Amy Santiago fell asleep, half laying on her fiance, with a smile on her face.
I really do hope y’all enjoyed reading this as much as I did writing it.
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THAT REUNION THOUGH. OFFICIALLY MADE MY YEAR. Y'ALL GO HOME, BECAUSE NOTHING CAN TOP THAT!
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Are there……. are there real men like Jake Peralta……. do they…..exist
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on another note how is it physically possible that andy samberg can say “cool” that many times in a row
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jake and amy’s relationship is one of the best heterosexual relationships i’ve come across in a while because:
it’s an interracial relationship between an ashkenazi jewish man and a latina (specifically cuban) woman
it’s genuinely loving, healthy, and dorky
they support each other and they make each other better. their relationship adds to their happiness instead of taking away from it
they always communicate and resolve conflicts maturely
they retain their independence, personalities, goals, and ambitions while still sharing each other’s hobbies and ideas and enjoying each other’s favorite activities
they don’t let their relationship get in the way of their career, goals, or obligations
they have their own lives outside of their relationship and we actually get to see them navigate the lines between a professional and romantic relationship
unlike most het ships, amy’s autonomy and personality aren’t reduced to jake. she isn’t jake’s love interest - she’s a main character of her own and her relationship with jake is just one part of her storyline and character
unlike most het ships, jake doesn’t bemoan being in a committed relationship. he loves amy wholeheartedly and is willing to do anything for her, and his friends actually support him instead of mocking him for that
they were friends before anything else. which means that they actually have fun. there’s nothing toxic or unhealthy about their relationship because it isn’t mired in heteronormative, misogynistic stereotypes. that is, they have a realistic and authentic dynamic because it isn’t all about ~ooh passion and melancholy and angst~. they’re cute and fluffy and it’s always presented as a good thing
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Don’t ask me to say that I don’t love you.
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Oliver completing losing his shit because of Felicity.
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