Day 1
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"…you have 365 days to ensure the continuation of the Hatake bloodline…"
That sentence ran through Kakashi's head repeatedly as he stumbled his way into a bar- knowing that the amount of liquor he kept at his apartment wouldn't be nearly enough for him to deal with the fact that he was ordered to become a fath- settle dow- dammit-
He couldn't even manage the thought. Nearing six drinks in, his nerves were calmed enough for him to start seriously considering the task ahead of him.
It couldn't be stranger as that would take years for him trust another to even consider having a child with them. But there were very few females around Kakashi's age that he knew enough to obtain thoughts of them being potential candidates;
Hosono Ayame who was two years younger then him at age nineteen, the daughter of Hosono Teuchi- he knew her from when he ate at her father's restaurant, Ramen Ichiraku.
Inuzuka Hana also age nineteen and daughter of the Inuzuka Clan Head, Tsume- her he knew from when he took his ninken to get their health checked.
Kato Shizune, age twenty-five and medic-nin training under Tsunade- he met her as a child before she followed her teacher from the village and they sporadically kept in contact through letters (Shizune was unacceptable as she wasn't in the village and unlikely to return unless Tsunade decided to).
Mitarashi Anko a year younger then him, a swiftly rising star in T&I- he met her back when she first started out in the division, dragging in a missing-nin for interrogation.
Oribe Sukui, twenty-one years old and a medic-nin whom made a name for herself in R&D during the war- her he met when he delivered news of Rin's death, she brought him a bento now and then when she joined him during his vigils at the Memorial Stone.
Uzuki Yūgao who was twenty and not even considered as she was the closet thing he had to a little sister since she was part of his ANBU squad and therefore forever his little kohai.
Yuhi Kurenai, three years older and entirely off limits because of Asuma- who he knew thanks to Asuma.
Which meant that there were really only three potential candidates- a civilian, a medic-nin and kunoichi whom specialized in torture.
This swiftly brought his drinks up to ten. When he wondered if this meant he was to marry, he quickly lost count of the number of drinks he had.
Because there always needs to be a 365 challenge/romcom bit.