I really love Sai and SaiIno. From your blog, I don't think you care about it that much, but in the future, if you're in the mood and have time, do ypu have any headcanons for who confessed to who and how the other reacted, and their first kiss? (Sorry if this was harshly worded or too much to ask foe)
I’m a huge fan of all the canon ships Anon, that includes Sai and Ino. But I tend to just answer what I’m asked about. If people don’t ask about SaiIno, then I’m probably not gonna talk about them that often.
As for your other question, let me recite to you an excerpt from Sakura Hiden, Chapter 1 Section 6, which recounts a conversation between Sakura and Ino regarding their love lives:
“Aside from that, how are things going for you, Ino? Nowadays… what’s happening in your love life?”
Since childhood, Sakura and Ino were frankly both rivals at heart over Sasuke. However, as they matured together, it felt as though Ino had stepped down from that race.
For now, who was Ino thinking about? Or who was she even not thinking about? (Sakura) wanted to know.
“Mmm…..Well, there is someone (whom I’m interested in)”.
Ino replied in an embarrassed and shy manner.
“Err…No, I don’t. It’s because I think of him well, so there is someone (whom I’m interested in).”
Unintentionally, Sakura approached beside Ino.
“I didn’t know at all. What? Who is it?”
“You’re really sinking your teeth into this, aren’t you, Sakura?“
“But it’s on my mind. I want a hint. A hint!”
“ A hint, eh?”
Ino thought about it for a little bit. Her face was slightly flushed.
“….it’s someone who’s skilled at drawing”
“No, that’s still not an answer!”
Sakura then retorted.
“Humph, I see….so it’s Sai?”
“But it’s not surprising, right?”
Sai was Sasuke’s replacement within Team 7. When Sai was first incorporated into their team, Ino had an interest in him. She showed (that sort of ) attitude towards him. Ino had said that he resembled Sasuke-kun a little bit with his attractiveness.
“At first, wasn’t he a rather good-looking guy at least? But I don’t know how to explain the feeling. Now, I’m completely (into him)…Eh, what is this!? Didn’t I just…. say so many dreadfully embarrassing things? Wha–!, Hi—!“
“Calm down, calm down….”
Sakura then asked while soothing Ino:
“Well, by the way… did you confess your love?”
“About that….well, I still…”
Ino’s voice became small. That reaction was surprising to Sakura.
In relationships with another person, it’s a relatively straightforward situation: If you make up your mind (to do something), you could immediately carry out your plans. Ino had an image (of what she intended to do). But now in Ino’s case, it somehow seemed to be a different scenario.
“(Should I give him) lavender? Or a flowering dogwood?…..I’m indecisive.“
Ino had said.
“Lavender? Flowering dogwood?”
”Yup…..In the language of flowers, lavender means ‘I will be waiting for you’. As for the flowering dogwood, it means ‘accept my feelings’ in the language of flowers. When should I show Sai the atmosphere of my feelings?…Am I supposed to be waiting on him? Or maybe like this…. Should I do my confession with a ‘bashii’(/sudden whack) ?……..It’s worrisome right now (for me).“
“(Oh, I see what you mean)”
Ino was indeed the daughter of a florist, since she was giving the explanations for the language of flowers.
“But Ino…. I think that your image is (more like the) flowering dogwood.“
Sakura was trying to say it. Ino then also nodded.
“Isn’t it?…. It’s like my personality, right?….”
Well….she said that she was worried. Ino had put her hand against her (her own) forehead. Somehow, it seemed a little sweet (to see her acting like this).
‘As for my situation’….Sakura was suddenly thinking:
It’s lavender, I suppose…Of course it is…..
‘Accept my feelings’….No matter (how much) she tried to say it, Sasuke was away from home.
As for Sakura, she could only wait for now.
However, she was then thinking:
How long will I be waiting…?
From that passage, it appears that Ino was planning on confessing to Sai relatively soon, so I think this pretty much confirms that Ino confessed first, and she did so by offering Sai a Flowering Dogwood, as a means of asking him to accept her feelings. And judging by how close they appeared to be with each other during Naruto and Hinata’s wedding:
I can only assume that Ino’s confession yielded positive results rather quickly :) I imagine that when Ino eventually did confess, Sai drew a replica of the flower that she had just given him using his ninjutsu, and said something like,
“Please take care of me, Miss Beautiful”.
Because just how fitting and awesome would that be? ^_^