Author's Note: A special thanks to my beta WishMeSwell for all her help.
Snapshot
#1 – fading: Jiraiya finds it funny; as he lays dying in Ame, his conscious mind clouding and dissipating like mist on the wind, his thoughts are only for Tsunade.
#2 – competition: She tauntingly dangles the bells in front of his face with a cheeky smile, and he desperately tries to figure out a way to break off the pole he is tied to and wipe that crooked grin off her face.
#3 – divine: As Kakashi reads his favorite of Jiraiya's novels, the one where the hero falls in love with a beautiful goddess, he clings to every word, but he never fully catches on that the goddess is based on his Hokage, who currently sits in her desk chair about twenty feet away.
#4 – shame: When he comes in with Naruto to the bar she has all but claimed as her own, where Jiraiya and Tsunade reunite after over a decade of separation, it is not that she does not want to see him; it is that she does not want him to see what she has become.
#5 – before: Back before they are put on a team together, before they attend the Ninja Academy, the four-year-old, village princess Tsunade thrusts a couple cards in front of a grubby, white-haired orphan and asks him if he wants to play.
#6 – nostalgia: "You were so beautiful back then," he says, the two briefly braking from the discussion on how to infiltrate the Rain village by reminiscing about times long past, and she really hopes he does not see the blush that forms on her face.
#7 – joke: This may be the greatest prank we've ever pulled, Jiraiya, reflects Tsunade, as she watches over two dozen kunoichi chase after a bewildered Orochimaru and beg him for dates, and she wonders how they actually managed to convince the girls to go along with it.
#8 – pretend: Hiruzen, Tsunade, and Jiraiya all like to tell themselves that Orochimaru was never their friend—that he was a scheming, twisted monster from the beginning—because they know that it is far easier to bury the good than to keep on reliving the memory of the traitorous, wicked smile that revealed the evil in his heart.
#9 – new: "His name's Dan," announces Tsunade one morning, as she fiddles with the rose her new boyfriend gave her, and Jiraiya spends the next forty-eight hours mumbling to himself about how Dan is probably stupid and that he does not come remotely close to being worthy of her attention.
#10 – voice: None of the Sannin can sing, but they all agree that some of the best moments they ever shared as a team were spent around a warm campfire, belting out Mist, love ballads, drinking songs of the Sand, and the occasional Iwagakure rap.
#11 – disappear: Jiraiya tells her that he is going to stay with the three, clever orphans that managed to track them down for food, and she is not sure why she feels betrayed when he leaves.
#12 – accidental: One of the only times they ever kissed was when he returned home safely from an exceedingly dangerous mission and without even thinking she pressed her lips up against his, before she remembered that her other two teammates were standing right there.
#13 – secret: She will never, ever tell him, but she has read every single one of his books, albeit purchasing them while under an absurdly realistic transformation jutsu.
#14 – proud: Tsunade watches with a proud smile as Naruto is announced as the sixth Hokage and knows the Jiraiya would have loved to be standing next to her, cheering along with the crowd as Naruto takes the stage like his father before him.
#15 – comparison: He has traveled the borders of the known world, explored vast caves and endless oceans, visited hundreds of cities, and even traversed a land reserved entirely for frog sages, and yet no matter how many women he lays eyes on, he has never found a woman that compares to Tsunade's beauty.
#16 – curious: Sakumo Hatake gushes about his fiance before asking if there's any girl Jiraiya is interested in, and he casts a longing glance at Tsunade before lying and claiming there are actually thirteen.
#17 – contraband: They are thirteen and guzzling down sake when they hear Sarutobi-sensei returning, and after a moment of panic, they hastily toss the bottle into the river.
#18 – tragic: It is a tragedy worth the greatest epics known to mankind: a man loves a woman his entire life, and when she finally starts to return his feelings, she gets a message that he has fallen in battle.
#19 – despair: Tsunade nearly collapses to the ground in grief when she hears the news about the death of her little brother, and Jiraiya soundlessly pulls her into a tight embrace and lets her cry until she falls asleep in his arms.
#20 – necklace: Despite her sensei's wishes for Jiraiya to succeed him as the leader of their village, Tsunade silently makes a vow to never give him the necklace in spite of her own opinion on the matter, because she cannot stand the thought of losing him too.
#21 – window: At first, Shizune was surprised when Tsunade allowed Jiraiya to break into the Hokage's office, stomp on her paperwork, tell her to forget it, and drag the blonde kunoichi to a ramen shop at whatever odd hour he chose to show up at that day, but after witnessing the event so many times, she became used to the odd presence sitting on the window seal waiting for the Hokage and accepted it with a knowing smile.
#22 – preserved: "I'll find a way to stay young and beautiful forever," a fifteen-year-old Tsunade promises, as Jiraiya scoffs that she will never manage to pull it off, but when they are both fifty and she is as radiant as ever, he cannot help but appreciate how brilliant she truly is.
#23 – unique: Jiraiya writes what he knows, so his novel about the goddess and the bold young hero - based on Tsunade and Jiraiya himself, respectively - is the only one where the main protagonist never actually gets the girl.
#24 – birthday: For her first birthday spent with her team, Jiraiya promises that he is getting her the best gift on the planet, but Jiraiya being Jiraiya, the so-called best gift ends up being a toad.
#25 – married: His favorite mission they were ever assigned was the one where he and Tsunade had to disguise themselves as a married lord and lady from the Land of Water to gain intelligence on an upcoming attack on Konoha; he spent the time calling her ridiculous pet names just to irritate her and forgetting Dan ever existed.
#26 – celestial: Jiraiya and Tsunade sit in a grassy field in some foreign country at three in the morning as a thousand stars glitter overhead and reflect in her eyes, and he swears she has never looked more beautiful.
#27 – promotion: As all of Team Seven downs endless bowls of ramen as they celebrate Jiraiya becoming a jonin, Tsunade can't help but admire how good he looks in his new, army-green, flak jacket.
#28 – rocks: He tries to teach her how to skip stones, but with her astonishingly strong arms, she flings the pebble so hard the she ends up tumbling face-first into the water.
#29 – start: A romance spanning nearly fifty years started with the words, "Hi, I'm Jiraiya, but you can write me a love letter later."
#30 – flush: Tsunade tells him she will kiss him if he wins the hand, and she knows she must be losing her mind when she folds her royal flush and leans in.
#31 – release: He watches the broken mess of a woman, still numb with grief over the loss of Dan, walk through the exit gate of Konoha with a young Shizune in tow, and knows that no matter much he wants to keep her by his side, he has to let her go.
#32 – mistaken: Jiraiya proudly shows off his genin team to Tsunade, and Minato, with a wide-eyed, childish innocence, asks Tsunade if she is Jiraiya's girlfriend.
#33 – records: The history books tell the tales of the great ninja, tools for their country to use at their disposal, but they will never mention the stupid things the Sannin did, like spitting contests, prank pulling, and intentional D-rank mission failing, because no matter what textbooks might say, before they were mindless weapons, they were once children.
#34 – brave: She is in the middle of a meeting with an elder toad when she learns of Jiraiya's death and it takes all of her courage to ignore her heart breaking in two to stay composed until the village elders leave.
#35 – cheat: He bets that she cannot retrieve a kunai he sticks at the top of the tree without using her chakra to walk up the trunk, but she finds a loophole in his logic, punches the entire tree down, and unhooks the knife.
#36 – method: For the longest time, Tsunade wondered how Jiraiya managed to copy down her answers during the written portion Chunin exams without using a single jutsu, and he finally revealed that he simply glanced over her shoulder when no one was looking.
#37 – counter: She tells him she has no idea how he managed to become a master of espionage with that shaggy, iconic mane of white hair, and he counters by asking how she still managed to become a shriveled old hag with a jutsu that kept her looking twenty.
#38 – unlucky: She throws her bottle of whiskey at the wall in a stupor, wondering why the one time she wins a bet is the one time she does not want to.
#39 – habits: He spits out his drink and laughs until he cries when Tsunade reveals that the highly esteemed First Hokage of Konoha is the one that got her into gambling.
#40 – hope: "You taught the brat the Rasengan?" asks Tsunade incredulously, because for the first time in a long time, she knows Jiraiya believes someone might have a chance at fulfilling his prophecy.
#41 – summons: "Summoning jutsu!" they scream in unison, both trying to have it mastered before the other (because after all, who needs teamwork when one has competition?).
#42 – hair: When she wears her hair in pigtails for the first time since she was little, Jiraiya remarks that he loves the look of it, and suddenly, pigtails become her part of her normal attire.
#43 – typical: The toads tell Jiraiya he will teach the one who will bring either peace or destruction, and his first thoughts are not about whether he can change the world, but about how impressive he will look to Tsunade.
#44 – betrayal: Orochimaru's missing-nin report is officially filed and the remaining members of Team Seven take a moment from their separate lives to cry.
#45 – babysitter: When she leaves Nawaki in Jiraiya's care for the day, she fumes when she returns to a filthy house; but when she observes her little brother and teammate slumbering peacefully in sleeping bags on the floor, she cannot find it in herself to stay angry.
#46 – footsteps: Sarutobi-sensei told them that in order to understand each other, they had to walk a mile in the other's shoes, so the two eight-year-olds took him literally and tripped and fell into the same hole.
#47 – familiar: At first she finds him exceedingly annoying, but after awhile the metaphorical (and on occasion, literal) pulling of her pigtails becomes habit, and she realizes she would not trade his teasing and smart remarks for anything in the world.
#48 – trick: She manages to convince him for an entire month that she has a weird habit of sleeping standing upside down from trees, before it finally dawns on him that nobody has flawless chakra control while unconscious.
#49 – symbiosis: A spoiled princess, a homeless, loud-mouthed orphan, and an introverted genius: nothing alike, but when put together, everything clicks into place.
#50 – paid: She figures now that she runs a famous village, she should start paying back all the money she owes, but when she goes to the man she is indebted to, he announces that everything was already covered by a man that called himself "The Toad Sage".
#51 – blizzard: Heavy snow and sleet atop a mountain trail forces Jiraiya and Tsunade to take shelter in a small, abandoned shack, and he mentally celebrates when he realizes they will have to huddle together for warmth.
#52 – war: The second the academy teachers step out of the lunch room, some white-haired kid yells "food fight!" and Tsunade ends up covered in ramen, but she is satisfied that she repaid her attacker in full with a smashed rice ball or ten to the face.
#53 – destruction: They stare blankly at the wreckage of a small ninja village, wreckage they caused, and wonder if the suffering will ever end.
#54 – heat: Under the sweltering summer sun, the future Sannin, currently just chubby-faced genin, swim with their friends in a refreshingly cool river and think that life would be perfect if it could just stay like this forever.
#55 – perfected: Konan hands Yahiko the portion of her fish that she does not eat with a giggle and a blush, Yahiko accepts it with a wide grin, and Jiraiya wonders how two kids so little could have reciprocated feelings for one another, when after several years, he still cannot get Tsunade's attention.
#56 – birth: "His name," Naruto says, handing Tsunade his newborn son, "Is Jiraiya."
#57 – honest: A drunken gambler and a miserable failure walk into a bar, and the punchline is that they call themselves two thirds of the Sannin.
#58 – bully: A couple of teenage idiots walk up to twelve-year-old Tsunade and begin to throw a train of insults her way, but before she can show the two punks exactly how powerful she is, Jiraiya already has them pinned against a tree, telling them that if they dare insult her again, they will not live to see sunrise.
#59 – motivation: She screams in agony as the tree falls over on top of her and she looks for something, anything, that will take her mind off the pain, to force her to keep pushing on, and the only thing that works is imagining Jiraiya cracking a joke that she is now half the woman she used to be.
#60 – coma: She has this dream, over and over again, that she is so close to him, but every time she tries to reach out, he shakes his head and tells her it is not yet her time.
#61 – spirit: Sometimes she hears his laugh, catches a glimpse of his impossibly unruly hair, or sees his smile before remembering that he is not there, that he will never be there, and she picks back up her bottle of sake and takes another drink.
#62 – innocence: Jiraiya and Tsunade watch students at the academy boastfully proclaim that one day they will be the greatest shinobi to ever live, and they remember a time that they did not think of the bloodshed and war the life of a ninja brought either.
#63 – ring: He had the beautiful ring he planned to give her when he returned home safely tucked in his pocket, and like him, it sank beneath the dark, roaring waves, lost in the abyss forever.
#64 – cheer: During the final round of the Chunin exams, she cheers on Jiraiya, but when he asks her later if she rooted for him, she tells him that she bet on his opponent just to aggravate him.
#65 – champagne: The clink of wine glasses could be heard over the fireworks, the laughter, and the festivities as they toasted another year still alive.
#66 – slumber: Sometimes she pretends to fall asleep while on missions so she can listen to him write his tales of dashing heroes, epic journeys, and bold romances, because when he believes he is alone, he thinks out loud.
#67 – first: Drenched in sweat, filth, blood, and grime, the newly dubbed Sannin proclaim their victory over Hanzō—the first battle Hanzō ever lost—before collapsing to the ground with exhaustion.
#68 – reincarnate: The villagers of Konoha whisper about how the modern Team Seven mirror the Sannin, but Jiraiya and Tsunade see how Naruto keeps on trying if he fails, how Sakura has an internal strength Tsunade never possessed, and they know that the mirror image only runs so deep.
#69 – doctor: "I'm going be a medic nin, guys," Tsunade tells them one day after training, and with a wide, earnest smile, Jiraiya says that he cannot imagine a better job for her.
#70 – prey: Like a single unit, they dance in and out of the battlefield, striking down foe after foe with chakra spirals and charged fists, earning themselves the reputation of the most powerful ninja of their generation.
#71 – bond: The first time the original Team Seven considered themselves to be true friends, rather than people they were unfortunate enough to be stuck with, happened when they selflessly guarded each others lives during a battle, and Jiraiya grudgingly admitted that his two teammates might not be so bad after all.
#72 – warning: "You really don't want to go in there, Shikamaru," Sakura tells the genius, and he is tempted to object until he hears the beginnings of a sob coming from down the hall, and he quietly turns the opposite direction and resolves to come back later.
#73 – home: Tsunade tiredly announces that her home burnt down the previous night in a freak fire, and she does not even get the chance to finish her sentence before Jiraiya tells her that his home is always hers if she needs a place to stay.
#74 – lines: A twelve-year-old Sakumo ripped the piece of paper Jiraiya wrote for pick-up lines to use on Tsunade and flatly told him that "you are like a candy bar—half sweet and half nuts", and "are you a campfire? Because you are hot and I want s'more", are the most idiotic lines he has ever heard.
#75 – cat: "Jiraiya, I want a kitten," proclaims Tsunade one day after a long training session, and somehow he ends up skipping the next day's regimen to take care of the ball of fluff that wanted nothing more than to use his long hair as a play toy.
#76 – age: Jiraiya knew he was getting old when his protégée started referring to the love of his life as "granny".
#77 – proposal: He bends down one knee, a ring in his hand, and she throws her hands around his neck in joy before he wakes up with a jolt and realizes he has been dreaming.
#78 – family: After Naruto comes home from strenuous missions, Jiraiya grabs Tsunade and the young boy for a picnic and shared popsicles beneath the leaves of the forest, just like a little family.
#79 – listener: Amidst the drinking, the gambling, the fear, and the debts, Tsunade kept her ears open to the gossip floating around the taverns, listening for any news about Jiraiya's welfare.
#80 – endless: Tsunade clicked her heels aimlessly, watched the seemingly endless days pass by before her, and waited around in her office with increasing worry at the lack of news from Jiraiya in Ame.
#81 – clever: He beamed as they caught up more than a decade's worth of lost time, fought the moony-eyed expression off his face, and became so wrapped in her beauty, her smile, and her mannerisms that he did not even notice when his crafty companion dropped a pill into his drink.
#82 – photograph: On the wooden nightstand in her bedroom, her favorite picture of herself and Jiraiya, one where they both are grinning like idiots and she is pumping her fist in the air as she sits atop his shoulders, remains one of her only possessions that she keeps from her childhood.
#83 – story: The three Ame orphans snuggle up beside him in their home, listening intently to his tales as the driving rain pelts relentlessly against the roof, and Konan, giving her best puppy-dog eyes, tugs on Jiraiya's sleeve and begs him to tell another story about "the pretty blonde kunoichi that he cares so much about."
#84 - revelation: There is no dawning realization, no one moment of truth where Tsunade recognizes her feelings for her white-haired teammate, only a nagging feeling in the back of her mind that just maybe she has been in love for quite some time.
#85 - memorial: After Jiraiya's death, she makes a habit of visiting the stone memorial where the fallen heroes of the Leaf have their name carved, and it becomes the only place where she allows herself to cry.
#86 - unconditional: Sarutobi-sensei once told him that real love was caring for someone even when it is not convenient, and he figures he must really have it bad as he cleans up after a violently ill Tsunade, taking the trashcan full of vomit out the door.
#87 - power: Tsunade and Orochimaru are absolutely shocked when Jiraiya summons huge toad for the first time, and after the battle ends, both ask if he will teach them how to summon too.
#88 - diamond: Tsunade's birthday had always been stressful for Jiraiya, mostly because he never knew what to get her, and Orochimaru always seemed to know what to get her, but when he sees a small, diamond, tennis bracelet in a store, he knows that despite its high price, he will give it to her.
#89 - carving: She learns the tree-walking technique days before Jiraiya gets the hang of it, but after spending hours upon hours falling on his face, he manages to climb above where she did, make a carving with his name on it right above hers, and leave it for her to find the next day.
#90 - dance: The Leaf village hosted a festival one year, and on the very last night as slow music played, Jiraiya and Tsunade danced beneath a grand display of fireworks, and just for one moment, forgot anyone else in the world existed.
#91 - perseverance: Despite Jiraiya's death, she places her focus on her work, researching the clues about Pain Jiraiya left for them, because she knows that this time around she has to be there for the village that needs her.
#92 - reckless: Tsunade patches up Jiraiya's wounds, careful not to hurt him any further, and scolds him for stupidly running into danger, and he protests until she tells him she just does not want to see him dead.
#93 - companion: At fifteen, Tsunade, Orochimaru and Jiraiya are best friends, and Jiraiya remarks that he cannot believe there was a time when three of them did not get along.
#94 - competitive: The villagers of the Leaf always dread when Jiraiya and Tsunade decide to compete against each other in anything, as their contests often result in property damage, irritated senior citizens, and in one specific case, an entire street flooded with mayonnaise.
#95 - tease: They playfully banter back and forth, their remarks becoming more and more clever as time goes on, until finally Orochimaru snaps, tells them to get a room, and to leave him alone.
#96 - paint: A thirteen-year-old Jiraiya remained unsure how Tsunade managed to talk him into it, but somehow, he ends up in her apartment, sighing as the red nail polish she painted on his toes dries.
#97 - faith: He smiles as she proclaims that she would never heal Orochimaru's arms, and he thinks to himself that he really should believe in her more.
#98 - slots: She spends half a day wasting her money in a casino, staring intently at the slots machine, and becomes absolutely livid when he sits down at the machine next to her and wins a large sum of money within fifteen minutes.
#99 - ice: They stare at a lake filled with frigid, icy water, and Jiraiya gets the idea to push her in, but the second he tries, his plan backfires as she grabs his hand with both of hers and drags him in with her.
#100 - ending: Long after everyone forgets their names, after she dies of old age many years after the conclusion of the Fourth Shinobi World War, two worn gravestones stand side by side, because if they did not get the chance to be together in life, at least they could try being together in death.