There may be some spoilers in this review, but mostly related to character and not plot. I don't want to spoil the book for anyone about to read it, since the element of surprise is definitely part of the novel.
I didn't LOVE this book, but I was amused by it. The writing is quite good: sharp, witty, clear. I love how Shipstead creates her characters here. They've existed long before we meet them, with their foibles and hang ups, but now that we're introduced, we are almost overwhelmed by the family, and the event that is bringing them together, Daphne's wedding.
I'd like to address a few things that really captured me about this novel. Primarily, the use of the whale as a symbol, intentional or not. The whole island is dominated by whale imagery, and it is also a preppy symbol, which embodies Winn's entire life. He is a man who wants to belong. If you hang a wooden whale on your house on the Island, Waskeke, you belong. If you wear a belt with ha;es on it, you also belong to a special club. The club that Winn currently wants to join is called The Pequod, which is also the name of the whaleship in the novel, Moby Dick. A sperm whale washes up on the shore, and of course, Livia, a marine biologist in the making, must see the whale in person. It becomes symbolic for her, too. Even Dominique has a whale experience. I had to laugh when Winn becomes like Ahab himself, with his bum leg after an unfortunate bike and golf cart accident. I also couldn't help but think of One Flew Over the Cuckoo's Nest--another novel that relies heavily on whale imagery.
Another symbol that I enjoyed being tossed about was that of the club that Winn was so very proud to have belonged to back in his Harvard days, the Ophidian. The name implies, a snake or dragon, a creature full of greed and full of itself. And Winn is so caught up in his college glory days, and his time spent at the Ophidian and what he just knew it meant to his family that he belonged to the club, that he becomes rather monstrous and obsessed. He has had daughters, and Livia (the one who attends Harvard) is not admitted to the club. He is disappointed first and foremost by this fact, and the fact that he has never had a son. he is a a man caught up in his own self image and desires, and while he doesn't always act in those desires, he behaves as a man who does, causing much pain for his long suffering wife. he also insults and hurts people around him with this tunnel vision, this long term course (he is almost 60) that he has set for disaster.
The main event of this wedding is the wedding of Winn and Biddy's daughter, Daphne, who is already well into a pregnancy, to Greyson Duff, who has several caddish brothers, and is definitely the catch of his family. Livia has been dumped, after becoming pregnant, by her boyfriend, who never really felt much for her in the first place. Their relationship heavily mirrors one that Winn had with jack's mother many years prior, sans pregnancy. Livia has told everyone she is pregnant and has also terminated the pregnancy, and has no qualms about continuing to pine for her lost relationship with Teddy, who is clearly finished with her: not because she is pregnant, but because they are not a good fit. Being at her pregnant sister's wedding i very difficult for Livia, and she is rail thin and pale, and looking for "love" (or something like that) on the rebound. Obviously, this is a big mistake.
Bad things happen to these people, and they have no shame. They are all trying to behave like some superior class of people, but their behavior is equal to something we'd see on a Jerry Springer show. There is embarrassment for what they do, and rarely any kind of apology (although efforts are made to get apologies, so many times.). Everything they do is done to themselves, or the ones that they have chosen to surround themselves with for this wedding: in other words, their closest friends and family. Dominique, Daphne's dear friend from prep school is the only sane one of teh group, who long ago threw away her whale belts and polo shirts. A beautiful Egyptian girl, she is both in with the family, but clearly the outsider looking in at an American family she once felt a part of, but can now see so many ways they've gone wrong, yet continues to be a friend, a lighthouse, a beacon in their dark hours.
By the end of the novel, you find yourself asking, what else could possibly happen? This is not an Austen novel (a friend who read it made this suggestion), with weddings and happily ever afters, and Livia and Daphne are no Elinor and Marianne, or Jane and Lizzie. But I can see where the structure could be regarded as quite similar, but no respectable Austen heroine would behave like a Lydia Bennett. Mopsy, the matriarch from the Duff family, is constantly complaining of being cold (no one ever suggests she bring a sweater, either, the Duff boys do everything to care for her every complaint, even when the air conditioning is not even on!), and at one point even she observes, "This family is falling into the middle class." (Of course, this is after a particularly stinging retort from the stoned and drunk Winn.)
This is a novel very much about fitting in, and getting what you want, even if you don't know that not only do you not really want it, but that you don't need it, and if you finally get it, it's going to hurt (kind of like a large, rotting whale corpse on the beach.). There were moments in the novel I felt like I was reading The Stranger, set on a tony up-East island instead of Algiers. At other times, I was laughing out loud, and that reminded me more of the feeling I had when reading Cuckoo's Nest--bittersweet.
I was surprised by the end. Although I don't believe anyone over the age of 25 is really ever going to change, I do believe there can be redemption and realization. And there is still time to move to the village of truth tellers. A fun summer read, if you can get past the initial obnoxiousness of these characters, who are really a bunch of people in pain.