Having feelings for someone like Shikamaru would go just how you'd expect.
Despite having an IQ of over 200, this man was practically clueless in the romance department. In fact... he could NEVER pick up the hints of those crushing on him in the first place. In the extremely rare case that he does, he gets all awkward about it and tries to brush it off.
Telling your friends about your current dilemma is no help either. When you told Ino, all she did was laugh and wish you luck. Sakura and Hinata tried to be supportive, and you won't even bother telling the guys, 'cause it'd pretty much be pointless.
Guess you're on your own for this one.
So you tried your hardest to make your feelings obvious.
You began to try talking to him daily, though it always ended on an awkward note. You started to buy stuff that he liked and gifting them to him, you even tried asking him out on a date multiple times (though, in your defense, you chickened out and asked him out to lunch with your friends instead of a proper date.)
He might be catching on. Though even might is too strong of a word.
Like always, you approached him with the intent of giving him another small gift. This time, however, he seems to have a different reaction to your advances.
"O-oi! You shouldn't keep wasting money on me." Shikamaru's brow twitched, holding his hands out defensively, almost like he was trying to block your little present.