Well he pretty much went with Hinata...looked at all the hints during the war....then look at the 615 chapter...he could have just tapped her hand...no he slowly grabbed it and held it. He then sent clones to simply tap Ino, and then several Nara and Akimichi clan members...Sakura wasn't even in the chapter...Notice at the end of the chapter he is back to where Hinata is, and he proceeds to lift up Lee's spirits....Hinata man
I think that things happen off-page in the manga. It's just that when it's not relevant to the story that it gets glossed over. So I believe it's plausible that Naruto could have made friends with soldier #275. Maybe they met during the timeskip and the are reunited in this war, and maybe there will be a Blossoming Love #275 Gaiden arc right before they share their first kiss. Is it requited love though? Will it get resolved during battle?
I think Sasuke is in love with Naruto. The proof is in the latest chapter, Naruto's power annoyed him. The people who have the power to hurt you the most are the ones you love. If Sasuke wasn't in love with Naruto, then he wouldn't have such powerful feelings like that just because Naruto has gotten stronger. In the end, Naruto will have to confront his feelings for #275 and Sasuke and make a choice.