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1. I wouldn't say he thinks about Tenten aside from when he has to, and that's only when he has to plan things with her (if any at all in archery) or when he has to talk to her. She's just another girl that has a thing for overpowering men because she's a feminist, and he understands that. It doesn't mean he has to agree with it. This leads him to take a similar way of approaching Tenten as he does with Sakura—disagreeing with her just because he can, in the most logical way possible.

As a person and as a girl, he doesn't really have an opinion of her. But don't feel bad! He doesn't really have an opinion on people unless they're really important to him (this is canonically Team Asuma, Team Shikamaru, Kurenai, and maybe Temari but not as much as the Konoha-nins).

2. Probably the summer between his sophomore and junior year of high school. That was when his sensei would play shougi with him , with the stakes of paying for Chouji's meal tab. It's not really the countless games he played during that summer, but rather the quiet atmosphere that accompanied it. The summer breeze, the smell of cigarettes, and the sound of cicadas around the balcony of his sensei's apartment.

3. No. I actually have a backstory for this! Sort of. It's flexible and it might or might not be the girl you think it is but lmfao hi. 8)

When he was fourteen, he met a high school girl about three years his senior. He was getting bullied and about to get his money taken away (which he had the situation under control with a makeshift foolproof plan), and she barged in his life by taking him by his hand and dragging him away. Typical story of boy meets girl, girl meets boy, except the situation is nothing beyond the fact that he was on his way home and she was lost. He gave her directions back to her apartment like any person would, and promptly parted without much of a thought in his mind.

It was later that night that he was doing errands for his mother when he ran into the girl again in a park near his neighborhood. Without much of a thought, because girls shouldn't be left alone in the dark, he kept her company. They talked about everything and nothing, and once again, they parted without much thought on the subject.

Every so often they met at the same park, and it became more like a scheduled thing for them. Sometimes they talked, and sometimes they sat around not saying a word. But it all worked out, you know? A couple of months passed and this became a regular event in both their lives, and one day the girl came to him with a piece of news: she was moving away. They wouldn't see each other again, because the park was too far away. There was also a whole bunch of business that Shikamaru won't ever disclose to others because it's not his place to (and I want to give flexibility if anyone wants to use this backstory), but by the end of the night they became a couple. A low-key couple but still. A couple.

A couple of years passed. The girl move onto college, and Shikamaru moved onto high school. And as life revolved around them, the girl began to notice that Shikamaru was rapidly becoming an adult. Not in the way that most perverts would think of that sentence, but in the way that despite his laziness and indifferent attitude, Shikamaru was a pretty nice and dependable guy. There were some ups and downs in the relationship, but somehow it managed to last four years, until Shikamaru hit eighteen. I assume they broke up because the chick went abroad or there was some irreconcilable differences. I like the first option better. But they parted on pretty good terms, I'd think!

He probably lost it around sixteen or seventeen. 8)