I've had this idea in my head since chapter 498. When Kushina tells Naruto that Minato was the first person to ever compliment her red hair, and that's when she fell in love with him. But, I don't think Naruto could ever be this smooth.
I can imagine Naruto do something with Hinata from the story his mom told him about how she and his dad fell in love and Naruto saving Hinata like how his father saved Kushina and then compliment her hair and talk about the confession Hinata gave him. Thats when these two will both kiss and end up together. Plus, the way Naruto is complimenting her hair in this pic is cute, I like it.
Yeah it'll probably not happen like Minato and Kushina. It will probably be something like Naruto's curiosity about why she wears a jacket all the time and how he's never seen her without it. (Canonly speaking.) Asks her to take it off... she does relunctantly, mumbling about her big boobs. Naruto will probably say that her breasts are just right for her size, and probably squishes them without thinking. Then realizes what he's doing and braces for the punch that doesn't come. He'll be curious as to why he doesn't get punch only to find Hinata has fainted. -lol-
But no, he could possibly have a smooth moment and comment on her hair. It'll probably more a matter of curiosity though. Like "Why is your hair indigo when the rest of the your Clan has Brown Brown-Black hair.".... and she'll explains it to him, and he'll say something like. "Well it looks really good on you, it sets you apart as being unique and pretty. Something like a princess wearing a crown.".... of course she's going to get all embarrassed but pleased with that.