Megan and Tom met at Harvard twelve years ago and immediately fell in love. Unlike so many other of their friends who wanted to spend their 20s exploring, they were happy to commit early and grow up together. In their perfect bubble, everything and anything was possible. Or was it? Now, finally, 12 years later they’re ready to tie the knot, bringing together their family and friends on the beautiful Juan Island off of the Canadian west coast. And suddenly, the cap has been taken off the bottle and everything comes to a head: Tom’s best friend and best man Leo shows up and expresses his undying love for Megan. They had a one night stand back at Harvard and never told Tom. It was the ultimate betrayal they both have never talked about since. Leo is everything Tom is not – adventurous and carefree, he travels the world, and he has a wonderful and supportive family. Tom on the there hand, has a stiff, wealthy lawyer family behind him who have always judged Megan for her broken home and moderate upbringing. Wouldn’t life be easier with Leo?
Meanwhile, Tom has a secret of his own he has not revealed: He has joined his father’s law firm and they will be moving from New York to Missouri. He hasn’t dared told Megan yet because he knows it means she will have to give up her career as a journalist in the big city.
All of this comes to a head at the rehearsal dinner on Friday night, the eve before the wedding, when Tom’s father stands up to give a toast and announces that he has purchased a large home for the couple in Missouri…. Mean storms off. When Tom tries to find her, Leo approaches him instead and tells him he has always loved Megan and that they slept together all those years ago. Tom finds Megan and they are both crushed and disappointed with one another and decide to call off the wedding.
And so begins the loop they will now find themselves on: Megan wakes up, emotionally drained, prepared to tell everyone the wedding is off, when her mother walks in, just like the day before and starts talking about what to wear to the rehearsal dinner. Megan realizes her face looks fine, not cried out and covered with mascara. Gradually, she realizes she is back where she started. There is some relief in finding that Tom is also on the same loop. They now know things about each other they must decide to work through or forgive. Every day, they proceed a bit differently. There is the day they don’t give a damn, and get drunk and tell everyone off. There is the day they decide to flip out and Megan sleeps with Leo and Tom picks up a waitress. There is the day they try to run away, but the plane never leaves the tarmac. And then there are several days where they try to be kind to each other and take the time to be just together and talk. What does fate want? Through it all they must confront their inner demons: Megan must come to terms with her needy mother and her own behavior of always accommodating everyone else. Tom must confront his father and finally think through what he wants in his own life.
In the end, the process of working through these days allows them to find their way back to one another. They are freer than every before, they feel they can finally step into the world liberated from all the imposed expectations of everyone else. And so, finally, they make love and fall asleep. When they wake up, it’s actually the next day, their wedding day. They have broken the loop! The author leaves it open as to whether they proceed with the wedding or not (since it was a day or expectations and family and no longer felt like what they wanted) but makes it clear they will end up together – on their own terms.