After Jeff Winston dies in 1988, he wakes up 25 years earlier as his 18 year old self with all his knowledge of the next few years in tact. Given the chance to start over again, what would most people do? It is perhaps not a surprise that Jeff uses his knowledge of the future to get rich. Still, despite all his money, he isn't completely happy, and he dies again on the exact same day in 1988 only to wake up as a 18 year old yet again. This time, he chooses marital bliss and financial stability over extreme success and riches. No matter what, each iteration of his life, he dies at the exact same moment of his 43rd year. During his third "replay" of his life, Jeff discovers another person, a woman named Pamela, who is also replaying her life. They also realize that each iteration, they have returned at a later point, and that Jeff returns before Pamela.
The two of them fall in love, and spend various iterations together in different ways. One thing I kind of liked about the novel is that these people don't necessarily become wiser due to their extra time, and there are some choices they make that make them very unsympathetic. Part of this is that instead of enjoying the opportunity to live life over again, they waste a few lifetimes trying to find answers. In one of his lives, Jeff spends time involved in the drug culture because he is so unhappy about losing the life he had before and doesn't want to form any bonds or attachments. Even after Jeff and Pamela meet and fall in love, they don't end up together during every replay - since they come back later and later each time, they have opportunities to change their lives at different times. Jeff coming back at 25 rather than 18 for example means there are other things he now has a chance to redo and correct.
I quite liked the premise of the novel, and while there were choices that Jeff and Pamela made that I didn't like, I like that Grimwood didn't make his characters infallible. I know I sometimes wish I could start college over again with my current knowledge but I think that is something everyone can relate to. However as even this novel portrays, the past is the past, and the only thing that can be determined at this point is the future.