1. Ino: 1. She's his childhood friend, and while something without strings attached might be a possibility, neither of them would want that type of outcome because it might jeopardize their friendship, however dysfunctional it may be.
Sakura: 1. He's her student. Not only is that breaching the barrier, it shows that Shikamaru is prone to favoritism, and with Sasuke looking over him like a hawk on any vulnerabilities, he can't take any chances. Not that he's attracted to Sakura in any shape or form... really.
Tenten: 1. They just don't clash together as a relationship type of pair, imo. Shikamaru is a very particular person, and for him it's like a hit or miss type of thing. That, and he probably doesn't date down or across. :(
2. On a whim, like most things he's into (go, shougi, archery, biology, chemistry, TAing, &c.). He's not an addict though, I swear.
3. Himself, you mean? ;)
It's not that he's an insecure person as a whole, but that he's insecure about how dependable he is to others. He understands that he doesn't have the best personality in the world, but he'd rather stick to being himself than being fake and make lots of friends he can't trust. But he's aware that he has a shit personality and is willing to take full advantage of it. The problem is, if he makes a mistake, he'll dwell on it for a bit and blame only himself. Especially if it's a problem that spans a lot more than just himself. But there's really no use crying over spilled milk, so he'll move on, just as adults should.
He knows he's pretty damn smart, but sometimes wishes he wasn't. Life is boring when you know the answer to virtually everything just because he saw it in passing a couple of years back, or read it in a book, or had a conversation about it, &c. It's probably the reason why he's just so damn apathetic—he's bored to death. That's why he's never going to fully exert himself unless absolutely necessary; things would just be too troublesome if he did, and overall, even more boring than things are right now.
Physically, he doesn't really care.
4. Not changing his bank pin number after Ino figured it out. But he figures Ino and Chouji might need to fall back on it every so often, so... while there are times he regrets it (Ino spending his money like water, Chouji's restaurant tabs), there are times when he doesn't (when these two actually need the money and has access to his account).
5. His past major relationship (as noted before), and the extent of said relationship. I doubt even Ino knows the full details about it past what little details she's managed to dig up. Not even the chick's name ohohoho.
/SLITS WRISTS WANTS AN EDIT BUTTON
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