The House of Mirth by Edith Wharton (1905)
Lily is clearly attracted to Lawrence Selden, and he to her, but he is not rich enough to keep her in the lifestyle which she insists is necessary. So she looks elsewhere for marriage prospects, pursuing Percy Gryce and then Simon Rosedale, neither of whom she actually likes and both of whom she fails to secure. In an attempt to invest what money she has, she seeks help from Gus Trenor, which turns out to be a huge mistake.
Gerty Farish was Lily's most stalwart friend, though ironically everything Lily did was to ensure that she didn't end up like Gerty, who was unmarried and lived alone in a small, modest flat and was excluded from fashionable social circles. I actually really liked Gerty who was probably the most genuine person in the book - being excluded from society means not being beholden to its requirements.
If Lily has a nemesis, it is surely Bertha Dorset, who contributes mightily to Lily's downfall. Bertha is notoriously unfaithful to her husband but deflects attention by spreading rumors and gossip about other people. She uses those around her for personal gain, manipulating them to serve her purposes. Lily comes into some evidence of one of Bertha's affairs and could have used it against her to help secure her place back in society, but in doing so would have also implicated Selden. As much as Lily could have been seen as being shallow and self-serving, she was definitely true to Selden.
I have no idea if high-falutin' New York society was actually anything like this during the Gilded Age, but if so I'm extremely glad I was not a part of it. Navigating one's life required the most intricate military precision, and I don't care how shallow and ridiculous you think these women were, they had to be smart and strategic in a way that I would completely fail at. I would have been eaten alive. At one point Lily laments: "All Jack has to do to get everything he wants is to keep quiet and let that girl marry him; whereas I have to calculate and contrive, and retreat and advance, as if I were going through an intricate dance, where one misstep would throw me hopelessly out of time." The language throughout the book reflected this strategic approach; for instance, when Lily doubts that Bertha Dorset's behavior towards a man will be sufficient to "effect his capture."
I've read three other books by Wharton and I don't recall the writing being so dense, but this took me a full week to read, which is unusual for me. I really enjoyed it until late in the story, and I'm trying not to let the ending color my impression of the whole thing. It did at first, but thinking back on it all to write this post has actually made me feel a bit better about the book as a whole. (It's a totally legit way to end, but just wasn't what I wanted to happen.) The social commentary was excellent and it was absolutely worth reading it just for that.
The House of Mirth was the March selection for the Classic Book a Month Club, and the first that I read for the year. I'll also be participating next month by reading Tender is the Night by F. Scott Fitzgerald, which has been on my To Read list since I first had one, and which I managed to not read during my 2015 TBR Pile Challenge. This will finally be the year, folks!