Two genre books here, not sure if ‘literature’ would describe either one of 'em, but…
Hitchhiker’s Guide to the Galaxy novels - Arthur/Ford and Ford/Zaphod. Admittedly, Douglas Adams doesn’t really do ‘relationships’ in these books at all – aside from Arthur/Fenchurch, and I don’t even remember that very well – but there’s a remoteness in the men’s interactions that always bugs me a bit when I read the books. They get irritated with one another pretty easily, rarely defend one another (though Ford shows some signs of protectiveness with Arthur, such as when the mice are after the earthman’s brain), and give up entirely on each other for years at a time.
I admit it’d be daft to expect anything better from Zaphod, who sometimes behaves like a sociopath, but I think more highly of Ford and so my expectations are higher too. I mean, sure, the books are light-hearted comedies and Adams wasn’t much for sincerity or warmth; such emotions are usually beyond the scope of the series. I adore the first three books, make no mistake. Still, I always wish I could engage a bit more with the characters than I do. I hope this isn’t too blasphemous!
Harry Potter series: No, I don’t mean Harry/Ron/Hermione. They’re pretty good examples of close friends with good relationships. I mean … is Harry as good a friend to Ron and Hermione as they are to him? Probably not, though I’ll leave that to others to decide. I think he’s self-involved, understandably so, but he still manages to be quite supportive. Spoilers below for Prisoner of Azkaban and subsequent books:
[spoiler]But the “worst best friends” I mean are the so-called Marauders, i.e. James, Sirius, Remus and Peter. On the plus side, there’s no doubt that James, Sirius and Peter behaved generously by learning to become Animorphmagi to keep Remus company; they kept his secret for quite a while, too. Sirius clearly thought the world of James and, I expect, vice versa.
On the downside: James and Sirius seemed to have looked on Peter with benign contempt, like smug, benevolent celebrity rockstars bestowing grace upon a roadie. Meanwhile, Sirius callously pulled a ‘prank’ on Snape hoping to let Werewolf!Remus attack/scare Snape, apparently not giving a crap that if Werewolf!Remus killed Snape, it would at least result in Remus being tossed out of Hogwarts, and quite possibly imprisoned if not outright executed. (Not to mention that gentle Remus would’ve been personally devastated.) After graduating, Sirius (possibly due to Peter’s influence) believed Remus was a spy, and apparently convinced James that Remus was untrustworthy, which is what led to Peter being the Secret Keeper in the first place. There appears to have been a rift between James/Sirius/Peter and Remus, evidenced by the distance between them in the photo of the Order of the Phoenix; this may have been because of Peter’s trying to stir up suspicion. And of course, all this led up to Peter performing the ultimate act of betrayal that got James and his wife killed, Sirius arrested and basically tortured for the crime, and Remus left friendless & alone.
Whew. With best friends like these…![/spoiler]
Edited to Add: ooh Lamia, Emma/Harriet is a great example!! Spot on.