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The only reason Sasuke gets all the women is because he uses an ultra secretive genjutsu... We all know when Konohamru hits puberty, he'll be getting all the ladies.
As for why Hinata would fall for Sasuke, well many good fanfics have played on the fact that she does admire the things about him that are similar to Naruto (courage, determination) but also that she empathizes with him greatly, and wants to help sooth his pain. Hinata's caring and protective nature comes in and tries to "fix" Sasuke.
With Naruto and Ino, things could be a bit different.
Naruto being attracted to Ino shouldn't come as a surprise as she's the best looking female in probably the whole series IMO (I like blondes). Not to mention she is a lot like Sakura, but not as tsundere. I've seen in fanfictions that people played on their relationship with Asuma, having Naruto's training with him extended so that Ino was exposed to him more.
For Ino, Naruto becoming the hero isn't usually it. What's usually the case for females outside of Hinata liking Naruto is watching him develop into a handsome and strong man with a big heart. With Ino i've always thought that having her use her mind reading powers to be exposed to the Kyuubi and Naruto's plight would also draw sympathy from her into feeling bad for him and admiring him more.
Outside of these two pairings these are the one's i've always liked, though could happen, or would like to happen or see (mostly in a fanfic).
Kakashi x Kurenai or Kakashi x Yugao
Shikamaru x Temari
Lee x Ten Ten
Neji x Kumo Female (I say this because I think the past hostility between Kumo and Konoha, specifically the Hyuuga clan would be intriguing, especially since it lead to his fathers death)
Sakura x Neji, Sakura x Gaara
I'm a SasuSaku and ItaSaku shipper, and even I don't take these pairings seriously if they don't happen, even though SasuSaku MAY happen. I did like SasuSaku when Sasuke wasn't a dick...
In the 'prettiest female', I think in manga universe, Sakura is the prettiest among the Genin 12 just for the reason she has the most admirers (Naruto, Lee, and random ninja) just based on her look. In anime, I did like Hinata, appearance wise, but in-universe, she's 'dark and weird' according to Naruto, and in manga, I think Ino's the prettiest even though post time skip her hair became too damn long, but all we saw in her attractiveness are: Neji wasn't affected, and Sai commented on her being lovely while thinking the opposite (to be fair, for Sai, Sakura is also ugly).
In the world of shipping, Sakura and Hinata is the new black. They can work with anyone. Even each other. I did have some SakuHina and HinaSaku fanfictions bookmarked...
Ewww. Sakura being the prettiest.... I just puked a little. no offense. (No i'm not a Sakura hater, I just don't like her character)
For the gennin, Ino and Hinata probably, from all the girls, SHIZUNE Don't argue with me there .
A new couple I'd like to propose is my man Orochimaru and Anko.
And Shizune and Kakashi.
If you want to freak people out then at least add Oonoki + Moegi to that list.
The only Old Generation X Young Generation pairing that would be somewhat acceptable to me is Shikamaru and Kurenai, because of the whole baby thing.
But, even this is pushing...
Although, Shikamaru is a pimp, so he can have all the girls!
Speaking of intergenerational relationships, What the hell is up with Sakura and Kakashi? It's The most prominent of this type. Where the hell did it come from?
Kakashi needs to find a lady
and I used to ship Sasuke x Anko so hard - couldn't you see it if the age gap wasn't as large?
....zomg, I just thought of Kakashi x Mei. THAT WOULD TOTALLY WORK RIGHT they're both old and lonely...
Normally I'd say Sasuke having no problems leaving Sakura to die, and only taking Juugo(just so he can use him) and Naruto(who he plans to kill) with him, would be the death of SasuSaku, but I've learned that logic doesn't work with Naruto pairings.
If you are a SasuSaku shipper at this point, you are willing to overlook a lot. Even Sasuke's total disinterest whether Sakura lives or dies.
Eh, I think it's pretty normal to ship SasuSaku at this point since SasuNaru shippers have no problem with Sasuke wanting to kill Naruto also (but no one called them out on it)
Yaoi aside, I did like KakaSaku since student teacher relationship is one of my kink. And the age gap is a draw without being too creepy.
SasukexAnko idea is hooootttt, especially since I liked OroAnko. I read a NaruShizu H doujin once, it's incredibly hot. And I agree that the guy who seem to have a connection with the ladies without being too dramatic or violent is Shikamaru. That guy has been hinted with Temari, Ino, and Kurenai (and Kin if you saw through a shipper goggles).
Shipping in Naruto can only be rivaled by Harry Potter. Everyone can be shipped with everyone. I read a Tsunade X Gamabunta fanfiction once, titled 'Princess and the Frog'. That... was pretty creepy.