That'll never happen. Honestly, since Shikamaru is so close to Naruto that if Naruto doesn't step up and confess or, at least kiss Hinata; Shikamaru will never get the courage or the cohones to bust a move on Temari. Its up to Naruto, it always is.
In my opinion, Shikamaru is better than Kiba. My brother told me that Shikamaru is very smart during a battle. But really, it's an opinion. You should watch more Naruto or Naruto Shippuden, and decide which one YOU think is stronger.