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#has his life ripped from him when sakumo dies
raikirikiri · 2 months
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since the naruto timeline is so… you know… inconsistent, for a word, i think it’s really funny if obito and rin are older than kakashi by some years. because then obito is really just having beef with a toddler like kakashi is 6 and obito is 9 or 10 and he finds this little feral dog child to be a major threat to his psyche. meanwhile rin has to be his voice of reason, saying no you can not hurt our 6 year old teammate, look at him he’s just a baby. and kakashi is snarling, on his hands and knees, barking like a chihuahua at them. and minato who’s a very busy jounin asks rin and obito to look after kakashi because he’s very messed up and could use a friend or two. but obito takes it as minato wants him to babysit his ankle biter teammate whom he loathes. but of course rin agrees and obito begrudgingly goes with her. and he doesn’t know how to deal with kids, being one himself, so he tries to boss kakashi around but little selectively mute kakashi glares at him and snaps his teeth at him any time obito so much as breathes air wrong. rin who understood minato’s assignment and asks if kakashi needs help cooking dinner or washing the dishes and is just generally friendly rather than bossy. obito still not understanding and trying to inflict bath time on a dog boy who viciously does not like water and the only people who can actually get him to take a bath are his dead father, minato, and pakkun. kakashi who likes rin enough and lets her sit on his furniture and kakashi who does not trust obito as far as he can throw him and growls at him when he so much as walks into the room. obito who’s had enough and decides to teach the baby a lesson. kakashi and obito who end up having a brawl in the living room while rin watches cartoons because hagoromo otsutsuki she’s just a girl! and she does not have the patience to deal with her asshole baby teammate and her stupid best friend teammate. minato who shows as up eventually and separates kakashi and obito and thinks they’re finally getting along until kakashi lifts his leg and pisses on the ground to mark his territory. the rest of team minato who finally realize that kakashi is actually just a puppy in human form and he is not housebroken…
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sanjuno · 5 years
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how do you reckon things would change if Obito and Kakashi remembered their past lives as Izuna and Kanna? (And have you given a past incarnation of Rin in the Warring Era?)
… @deverickracoma you mean, like in canon? Huhhhh…
Well first off before Rin was Nohara Rin she was Senju Touka. Which makes this situation super fun because both Izuna and Kanna died before Hashirama strong armed Konoha into existence and Touka only went along with it because Her Stupid Little Cousins Need Some Common Sense. XP
In her lives as both as Touka and as Rin she holds the single (1) braincell for this Disaster Trio.
So Izuna dies via Tobirama’s sword. And then Kanna kinda… revenge rampages with Madara until the critical angst threshold is reached as Kanna just… explodes both theirself and the battlefield. 
There’s a whole lot of background stuff behind the suicide run such as Kanna’s Hatake side suffering from mate-loss depression and their Uchiha side suffering from Makengyou Madness and also Really Bad post-partum depression compounding it and yeah. Unfortunately Madara is just as wrecked from Izuna’s death so he can’t really support Kanna and it all goes to shit because we all know canon is a shitshow.
But anyway Touka is there to see Izuna die and she is well aware that Tobirama has just made a horrible decision driven by unacknowledged jealously and overzealous paranoia. Then Touka barely manages to save Tobirama’s pasty ass from the screaming revenge demon that she later learns was Izuna’s wife. And then Touka stands witness as Hashirama forces peace at sword point.
So Touka is just there like, “Oh for fucks sake we’re all going to die horribly.”
And, of course, Touka was right everything is horrible and everything hurts. 
Only now it’s plot-twist time and Touka, who was investigating certain questionable sources about the ongoing breakdown of social order in Konoha gets killed by Zetsu in order to cause even more tension against the Uchiha in Konoha and hey guess what? Yeah, that’s right Rin remembers the creepy plant-demon thing gloating about stealing Uchiha Madara (aka the only one vaguely strong enough to combat Kaguya at that time given he had naturally manifested the Rinnegan) for his own use before Zetsu killed her in a suspiciously ambiguous manner.
Shit.
Fuck.
Four year old Nohara Rin has a vendetta and the ability to kill a grown man. 
So obviously given that the Plant Demon is trying to kill off the Uchiha using shadowy assassinations and rumour mongering the Plant Demon is afraid of the Uchiha. Ergo the Uchiha are a threat to the Plant Demon otherwise it would confront the Uchiha more openly.
So.
Rin therefore needs to make super-duper ride-or-die best friends forever with at least one (1) Uchiha. And then, on the first day at the Academy, Rin runs into an absolute dork wearing Madara’s face.
Ah. Says Rin, channelling canon!Madara. That One. That’s The One I Need For My Plan To Succeed.
Cue the Rin and Obito Bonding Moment ™ that will repeat as a flashback every time their history is at any point mentioned in the narrative.
As for Obito, well… when he was Izuna he loved his Clan but then when he was reborn he read the Clan Histories from after his death and the public history of Konoha and Obito knows his Clan are a bunch of fucking traitors who stabbed his big brother in the back and that’s why Obito is both disgusted by the Uchiha and overprotective of the Clan’s reputation because Madara still loved their Clan even after they turned on him.
I may include Obito unearthing Madara’s private journals from a hidden cubby in the Naka Shrine that only Izuna would have known to look for. Just for the sake of an extra knife and also so that Obito can find proof of Zetsu’s sabotaging his brother’s mental health. 
Obito is more than a little weepy and sentimental over the fact that Madara honoured Izuna’s last request to the point Madara destroyed himself and his connection to the Clan. Obito can’t blame Madara for giving in when Hashirama forced peace to try and protect the few loyal Clan members who remained. Obito decides to protect Konoha and the Uchiha because he won’t let Madara’s last wish go unfulfilled but he’s going to become the fucking Hokage and tear out all the Senju-inflicted rot infecting his Big Brother’s Dream.
Obito is openly disdainful of the Clan Elders and the only people he even vaguely respects is the Head Family. Mostly because Mikoto is descended from Izuna’s daughter and even though Izayoi married “Tobirama’s student Kagami” she was still his baby girl and Mikoto is his great-grand daughter and he loves her because she’s his family.
Mikoto, Obito, and Shisui are all descendants of Kagami and Izayoi’s kids so they’re second-third cousins. Obito spends a lot of time pondering the overlap of self-care and I-love-my-grandbabies. It’s a fun little exercise in existentialism.
In the meantime Kakashi is still a little shit-disturber of the highest order. Kanna was taught all the fun Uchiha Clan Skills as Izuna’s wife and now Kakashi has learned all the fun Hatake Clan Skills from Sakumo and the little bastard is even more terrifying than canon. Kakashi is more gender-fluid than agender the way Kanna was though which is a fun new flavour of dysphoria-through-reincarnation that I’ll probably enjoy exploring.
Now, this does mean that Kakashi starts wearing his mask before Sakumo gets scapegoated which is a minor yet still significant change from Kakashi’s canon characterization-and-motivations.
So Kakashi blitzes their way through the Academy in like, 6 months because Kakashi has negative chill and an understandably paranoid focus on keeping their dad alive this time around. The only people Kakashi respects are the Military Police and their Dad everyone else can perish. Minato is A Constant Despair because he cannot control this sassy hell child Sakumo-sempai pls tell your son to l i s t e n t o m e.
Sakumo-sempai goes “LOL nope” because Sakumo is also a troll but is better at hiding it than Kakashi is.
So Rin and Obito are BFFs then Kakashi rips through their class like ground lightning and the sparring scene happens but the kickback of Uchiha-memories manifesting as body action means the spar is a familiar dance and so Obito is like “OMG K a n n a” and cue Obito stalking Kakashi like a schoolgirl with an obsessive crush and no concept of personal boundaries.
Enough shenanigans occur to 1. make Team Minato a cohesive and functional thing instead of a train wreck, and 2. keep Sakumo alive because Kakashi recognizes their Dad’s suicidal tendencies for what they are and so they set their ninken up as watchdogs to make sure Sakumo doesn’t do anything stupid. Because Kakashi’s biggest regret is leaving Madara and Izayoi to suffer grief without them and they refuse to let that sort of despair take away anyone they care about again.
So now Team Minato is bonding, and they are friends, and they are all slowly coming to the realization that they all remember their previous lives. So they start to share information and gradually piece together where Zetsu’s influence has been applied as they try to figure out what the Plant Demon’s endgame is.
Which means that Team Minato is 100% more paranoid about mission intelligence than they were in canon and also Rin more than ready to gut the Iwa-nin who tries to kidnap her during the Kannabi Bridge Mission so that’s fun. Team Minato has also made a point system for rooting out moles, spies, and traitors to hand over to T&I. 
Sarutobi had a lovely headache when the knowledge that Sakumo’s mission had been sabotaged “accidentally” got leaked. (Kakashi had given the old man more than enough time to fix the rumour mill so it’s on Sarutobi’s own head that he didn’t take action before Kakashi did.)
Also Team Chaos Gremlins Minato manages to charm Orochimaru over to their camp via one of Obito’s rage fuelled rants about dismantling the hypocritical indoctrination of the institutionalized status quo. Specifically, the fact that the Hokage is supposed to be a public service position voted on by the people who only really has complete executive power during war time. Instead of a unilateral dictator chosen by the previous Hokage’s undisguised bias and favouritism.
Also because they’re all proof of the reincarnation cycle existing. Orochimaru is living his best life especially when Team Minato trash talks the other two Sannin. 
Rin is the Most Offended by Tsunade fucking off and abandoning her responsibilities. Tsunade basically inherited all of Hashirama’s worst traits without any obvious redeeming qualities to balance it out. Because, let’s be honest, the only reason Hashirama got any level of respect is because he was Over Powered to the point of ridiculousness and because Tobirama plus Mito were in charge of his public image.
Kakashi and Obito are both hyper-loyal so having Jiraiya decide to just not come back during wartime and for Tsunade to abandon her responsibilities as a healer and Clan Head has destroyed any possible respect they might have had.
Obviously Orochimaru is the best Sannin so he’s the one they’re going to make friends with. Also they drag Orochimaru back to the Hatake Clan House to commiserate with Sakumo about being the target of a Village wide smear campaign. Which strengthens both Orochimaru and Sakumo’s spirits enough to resist their Bad Endings from canon.
All of this basically allows Team Minato to have the leverage to track down Zetsu’s creeper cave and they find Madara trapped and blinded and leashed to the Gedo Mezo, and Obito nearly has a world-destroying breakdown. Rin stands guard while Obito and Kakashi have a tearful reunion with Madara and there’s a lot of dramatic apologizing and sobbing.
They all know that they can’t leave Madara here with Zetsu, but detaching him means he’s going to die. Eventually Madara makes the decision himself to break the connection because he refuses to be used as a hostage against his little brother. So Madara tells Obito where his eyes are (which means that the Ame trio are going to get kidnapped by Team Minato eventually) plus a run-down of all the subversive plots Zetsu has had a hand in, and then Madara outright smashes the statue.
Normally nothing would be able to destroy the Gedo Mezo given that it’s basically the fossilized corpse of a god but Madara is currently part of it which means that the statue’s defences don’t realize Madara is a threat. So, statue goes boom, the cave starts to collapse, and Team Minato runs away with Madara’s body so they can give him a respectful burial.
Zetsu has approximately ten thousand aneurysms in the space of one (1) second.
From here the kickback really starts to pile up because Obito now makes a habit of dropping in on newborn Uchiha to check and see if Madara’s been reborn yet. Which means that Sasuke has a really invested older cousin hanging around to take Itachi’s place when Itachi make dumb decisions.
Rin is grumpy because basically every Clan who joined Konoha had a bunch of Senju marry into their Clan so finding Hashirama’s reincarnation is basically impossible. (And then, of course, Naruto is born and Rin faceplams 1000 times because of fucking course.)
Kakashi is laughing at both of them. Right up until they take command of Team 7 and notice a hated familiar chakra under the skin of a pink haired little girl. (All three members of Team Minato nearly die laughing because Tobirama is a pink haired little girly girl heeeeee~)
Anyway aside from all the family drama Team Minato also manages to dispose of Danzo and exposes his “plot against the Hokage”, boosting Sakumo’s public image to the point he gets named as the Fourth, fixing the stigma Orochimaru faced despite being the only loyal member of the Sannin, and basically terrorizing Konoha with Political Activism.
Zetsu probably goes a bit around the bend thanks the Team Minato destroying all his hopes and dreams plans. Also they keep putting the pressure on and exposing Zetsu’s schemes and eventually that gains enough momentum that the other Villages are taking a good hard look at shit that’s going down and hey wait w h a t t h e f u c k …
Obito eventually takes over as the Fifth Hokage and tears apart the corrupt government systems like a Tasmanian Devil going through a rotting carcass because Big Brother’s Dream Will Become A Reality B E L I E V E I T !
The End. XP
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wasabi-mommy · 4 years
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Hello, this is a short 3 part fic I’m in process of writing.
Summary: Kakashi has lost the one he loves most, how? He doesn’t know. How is he is still alive? Also, he doesn’t know. Dealing with the intense emotions, the stress of change, and living without the love of his life is tearing him apart. Kakashi doesn’t know it, but he has people looking out for him though, Even if he doesn’t feel like it.
(Let’s base this before he has OG team 7)
Day By Day (1/3)
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Warnings!: ANGST, DEATH, BLOOD, ACTIVE VIOLENCE, MENTIONS OF SUICIDE.
He didn’t know what was worse. Couldn’t tell what hurt more... the first night knowing that she’s gone, or every single day after.
Kakashi was still awake, like he had been for the last 6 days.. no.. no it was almost morning now. No.. 7 days.. a week. His eyes glued to the ceiling of his “old” apartment.
Once more in his life he felt empty. He felt like a fucking idiot.. letting his guard down again- letting someone in. Again. Of course they would be doomed to die as everyone else Kakashi cared for would.
He didn’t even know how she died. He woke up to her body lifeless on top of his... He doesn’t remember who carried him to safety.. he doesn’t remember who hauled his half dead body 100 miles back to the village, he doesn’t even remember being in a medically induced coma.
All Kakashi can recall.. is waking up to his lover’s body on top of his, stained with cold blood , yelling her name and shaking her to wake up- to open her eyes.
Then it was black.
He remembers shooting up from the hospital bed, ripping off the wires and tubes attached to him, he remembers practically interrogating the doctors and hospital staff...”She bled out” the medics told him.
He sat up slowly, he was disgusted with himself, his body felt like sludge. His head fell into his hands, his face unyielding of any emotion but the tears streaming down his cheeks clearly say otherwise.
He crossed his legs as he stifled a silent sob.
He loved her. She was the kind, unselfish,sweetest, intelligent laidback person he had ever known.. and she didn’t even have to try, because that’s how genuine she was. Kakashi’s breathing gradually slowed and he lifted his head from his hands. He threw his legs over to the side of the bed and with all the effort of whatever was left in him, pushed himself up.
The funeral or the preparations atleast.. was what he would genuinely crushed him. She didn’t have any family, no next of kin, only him. He had to sign the release forms for her body at the morgue, he had to handle the paperwork regarding funeral arrangements. It was a constant sick reminder from the minute he woke up on an active battlefield.. that she was dead.
Kakashi’s legs were numb but managed to carry him to the bathroom just fine. He scanned himself in the mirror. His silver hair thrown in every direction, dark bags forming under his eyes from sleepless nights, his maskless face covered in scruff. He let out a short laugh followed by a small cry.
‘I should be ashamed of myself’ he thought staring down his own reflection.
The anger was carved into Kakashi’s face and he couldn’t hold it in anymore, with his knuckles white and a quick cock back of his fist, he’d lost it. The sound that escaped his lips as his fist easily went through the dry wall was one he’d never actually heard from himself before. It wasn’t like him to be this extremely outwardly violent.
The mirror fell off the wall and shattered on the tile floor, Kakashi’s breaths were heavy and his eyes fell below him. The glass had sliced his ankles and feet. For some reason.. he couldnt feel the pain, but he could see the blood starting to seep from the cuts. Other than that.. nothing.
“MR. HATAKE! WHAT IS GOING ON?!” A raspy female voice called out as she banged loudly on the front door.
“Shit” He mumbled. He’d forgotten, his neighbor was actually his landlord. He let out a sigh and rand his hand through his tangled hair. He can’t feel anything- at least in the moment so he walked without a care over the shattered glass on the bathroom floor.
He slowly turned the knob of the door revealing the short chubby grey haired women standing with her arms crossed.
“Mr.Hatake do you understand it is 4 in the Morning!? What are you doing punching holes through my walls?!” She yelled flailing her knobby arms around.
“I’m sorry Mrs. Roshi” she arms fell, she opened her eyes to get a closer look at his.
“Mr. Hatake! You’re bleeding!” Ms. Roshi grabbed his hand before he could protest and guided him through the door to the right of his.
“You sit down, I’ll fix you up!” She motion him to the living room while she waddled away. Kakashi found himself sitting on the sofa, hand folded in his lap, he could feel the dried tears along his cheeks, and a headache was sure to be coming along.
‘She won’t be offended if I just leave right? ..no i already put a hole through her wall.. she’d probably evict me at that point..’ he thought folding his hands into his lap.
Ms. Roshi came back with a large bowl of water, a small metallic bowl, medical tweezers, surgical sutures, alcohol pads, and bandages. She set everything down on the floor and looked up at Kakashi. She frowned, there was an emptiness that she could she through his dark eyes. Roshi herself had a feeling what had happened seeing that look in a mans before.
She lightly lifted up his heel and began to observe the wound soon plunking away at glass shards. Kakashi felt embarrassed, but he felt like he deserved this, this punishment or whatever this feeling was. The only noise filling the apartment where the small clinks of glass begin dropped in a metal pan.
Roshi broke the silence, “ what has you hollowed away Mr. Hatake?” Her voice was steady and calm, almost nurturing.
Kakashi’s eyes grew wide for a second and then appeared once again lifeless.
“I..” it was still so fucking hard to admit. Because when he would say it.. then it would become real, “ I lost a loved one”
Roshi nodded, “ I see... I’m sorry for your loss” Kakashi’s shoulders fell, even though he had to keep still for her he just wanted to fall apart.
“If I may ask, how did she pass?” Roshi asked plucking out a very large piece of glass from the side of Kakashi’s ankle. He felt like his heart would stop any minute with how shallow it felt.
“I-I don’t know..”
Roshi cocked her brow before she could say anything Kakashi continued,” I remember waking up during the battle..she- she was on top of me. I- she died.. she bled out on top of me”
Roshi’s face grew grim, “ that is terrible, I’m so sorry.” She began working on stitches the deeper cuts at this point. Old woman worked fast.
“How about I put on a pot of tea,Hn? Then I would like to talk to you Kakashi”
Kakashi’s head perked up, it caught him completely off guard, using his first name.
“I would like that, Thankyou” he hated how disgustingly pathetic he sounded. He just wanted to shrivel up and die in complete honesty. Ms. Roshi finished stitching up the silver haired mans feet and ankles and had wrapped them in bandages.
“Put on these socks for now, you shouldn’t walk bare foot with fresh bandages” she tossed him a pair of fluffy grey socks. Kakashi slipped them on and Ms.Roshi eventually slipped to the kitchen for a short and and brought two cups of hot tea and set them on the coffee table. She took her place in an arm chair across from Kakashi and sighed. Kakashi blew gently on the hot glass and began to sip the sweet warm liquid.
“I remember when I first met you and Sakumo,”
Kakashi almost choked on his tea, he put the cut down on the table, “you knew my father?”
Roshi smiled and nodded putting her tea down as well, “of course! I’ve rented to Sakumo all of your life Kakashi, I was very close friends with Sakumo until the end, I remember tiny little you..and now look another Hatake is renting from me now.”
She smiled, “ Besides who else would rent to a man with such bad credit like Sakumo”
Kakashi scratched the back of his head. “Uuuh well..”
Roshi Scoffed, “Kakashi you don’t even have credit, so shush, I promised Sakumo I’d give you somewhere to stay, why do you think you rent is only $50?”
Kakashi sweat dropped, he was learning a little more than needed about his father now.
“I’m not going to sugar coat it Kakashi, I’ve lost my Husband, 3 sons, and 2 daughters.. all Shinobi, some fighting for the village, some becoming their own demise..” she looked at Kakashi with serious eyes. Kakashi’s mismatched colored eyes locked with hers in the subtle moonlight of the living room.
“I need to know if you’re going to be okay Kakashi. I’ve lost two sons to suicide, and I wouldn’t want the same to happen to a dear companions son”
Kakashi tensed up. No, he wouldn’t come to that point.. a part of him wouldnt fathom the thought of taking his own life, only from the fear of not having succeeded and having to deal with the aftermath. There was a sick part of him deep inside that wanted to give in and waste away. Kakashi picked his cup back up,
“No.. I couldn’t” he mumbled gazing at his reflection in the tea, god he looked like shit enough for someone to ask him that?
A huff came from Roshi and she crossed her arms. “Good. You’re a gentle young man Kakashi, I know everything you’ve been through has been hard- but you cannot be lead astray by violence and self destruction”
Everything she was saying.. resonate led with him. Staring blankly into the dark liquid refracting the gleam of moon light that had slipped through the window.
Kakashi set the cup down and got up from the sofa. He flinched, yes he could feel what the broken mirror had done to his feet now. What a stupid, stupid, stupid thing for him to do.
“Thankyou Ms. Roshi, I’m sorry about your wall,” Kakashi’s eyes glanced to his left where he could see a hole clear through the drywall.
“... I will fix it in the morning, Thankyou for everything.” He bowed his head to her and turned to leave.
“Kakashi”
He looked over his shoulder, his hand already gripping the door knob. “... please come and visit me more often, talking can help.”
Kakashi looked back at her and forced a small closed eye smile.
“Thankyou Ms. Roshi” he said quietly leaving the old woman apartment.
He closed the door silently and slipped back into his apartment where the bathroom light was still on. Making his way towards the bathroom he saw how much of a mess their actually was, blood, glass, chunks of drywall. It earned him sliced up feet and ankles and still.. nothing has changed.
Lol I hope you enjoyed, this is part one of three, inbox me suggestion and stuff.. please don’t be rude this is my first fic that I’m posting on this blog publicly.
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peepingtoad · 4 years
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@kyugens​ said: What are Jiraiya's true thoughts on love? Has he ever considered giving up on his pining for Tsunade and settle down with someone else? He watched very closely Minato and Kushina's relationship, being his mentor and even naming Naruto, do you think he's ever wished to have a relationship like that? | headcanon asks | always accepting! |
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I think it’s pretty clear that Jiraiya, from a very young age, was always very preoccupied with romance as a whole. He met Tsunade and immediately flirted with her, over-confident little man that he was, and even possessed very little motivation to improve as a shinobi at first because he just wanted to get girls. I believe as well that he was always one of those kids who’d just casually say things like ‘when I’m married’ or ‘when I have a kid’... you know those type of kids (I was never, ever one myself pff).
So I think there was a general idea his young brain had formulated, even while it was still so tender and stupid, that he’d likely end up having a wife and a kid at some point.
Of course, life had different plans for him!
By his early teens he was finding his feet as a shinobi and apprentice of the toads, but there was still nothing that could prevent his desire to get out there and score smooches. He even got a girlfriend pretty young, although it ended as young romances tend to do, only to be followed by a few more scattered dates and little flames. At some point (possibly in his late teens) I think he even made a 100% serious confession of love to Tsunade, promising to be very faithful and everything, which of course didn’t end well.
But he wasn’t too dismayed, and ended up very enthusiastically sowing his wild oats wherever he possibly could, and generally being scornful of commitment and marriage... possibly performatively, or even just to play up his rebellious, ~dangerous~ side. We see from that one filler arc that he claims his heart will always belong to Tsunade—which I believe is true, in the deepest sense—but his big polyamorous heart always was capable of feeling love for more than one person. Perhaps, in the end (and this applies to Orochimaru too, because he was seriously in love with both of them), he simply had it in mind that while he could love others, it would never be That Love. That it couldn’t ever develop into That Love... and, well, I suppose there was never enough time spent in any given place or with any given person for him to really be proven wrong. So the specific love he has for those two ended up being put on a pedastal and sort of glorified in his head as being the loftiest and most unattainable love, and the rest is chasing affection and pleasure while having this Thing in the back of his mind/heart that keeps him self-sabotaging wherever other opportunities may lie.
Basically, he hinders himself a lot by being hung up and pining over those two, while treating love as something of a game to be played, to be won at times and lost at others.
I do think there is more to it, however. When we take Sakumo, whose wife died when Kakashi was tiny, and Tsunade, who lost Dan... it puts a chilling fear in him, of having that truly sublime love, only to have it ripped away. This again comes to haunt him with Minato and Kushina, with the fact they died together making it no less tragic, and having seen the makings of the wonderful family they would have been. Of course, observing them (especially throughout Kushina’s pregnancy) is a heavy reminder of those things he innocently wanted—and honestly expected—to eventually have as a kid. Things that now, he isn’t sure he ever can have, and not only because his biggest loves have always been unrequited (Tsunade) or riddled with too many complications (Orochimaru). So he turns to writing, which is really where he escapes and puts into words the light and idealised romance he always prized. The type that always had ups and downs, drama and joy, while still ending on an uplifting note.
As for ceasing his Tsunade-pining and attempting to settle down... There’s a headcanon I’ve had lurking around in my head for... whew, a good while now, which I don’t recall ever being certain enough on to write down. But since I’ve thought about it for so long, I’ll make it official.
At some point in the blank period between the Kyūbi attack and his return to Konoha during the Chūnin Exams, Jiraiya was finding more and more leads as to where Orochimaru had holed up. The leads took him to the Land of Rice Paddies (which had yet to be renamed to Land of Sound at this point), and since they were such strong leads he ended up staying in this country for around two years, putting his all into finding the Hidden Village itself—although he was gradually beginning to lose hope. Anyway, in one of the larger towns he stayed in there was a performer and prostitute named Okuni with whom he became rather taken, and eventually ended up practically living at her house for the duration of his investigations under the pretense of it saving a few pennies on constant hotel stays. Needless to say, this was a transparent excuse at best given how close they became and, for a time, how Jiraiya seemed to forget just about everything outside of this life he’d accidentally fallen into.
Sadly, this would end when someone he’d interrogated and shown mercy to blabbed to an Otogakure spy, who took his sweetheart hostage. He was able to save Okuni and help her relocate, get set up with a new life somewhere else, but it was a close enough call to remind him what so often befell shinobi in love.
But that was probably the closest he ever got in his lifetime to truly settling down with someone.
From there, of course, he ended up eventually becoming involved in Konoha’s affairs once more, and had to seek out Tsunade when Hiruzen was killed. And when they were reunited, it was undeniable just how in love he still was with her. But he kept it quiet, knowing that even if she did feel differently about him than she used to, it was just asking for more hurt on both sides to pursue anything. Which, as we know, culminates a final conversation between the two that is laden with implications that maybe, just maybe, if they both made it through all this alive they could finally give it a go. 
Because really? That is what he always wanted to have with someone—a real, true romance. He may have slept around a lot, been a thoughtless bastard and left numerous broken hearts in his wake, but he really was always chasing love in his own unorthodox way, in whatever capacity his lifestyle would allow. He even rediscovers his hope in bringing Orochimaru around, through Naruto, because the love he has for him is still so strong (a tidbit from the databook that my shipper heart took a Certain Way).
(For an extra bit of throwback flavour, please see this old as hell headcanon on the topic of saying ‘I love you’ that I found, which I think still perfectly sums him up in all his messiness!)
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