Cassandra Penelope Dankworth is a creature of habit. She likes what she likes (museums, jumpsuits, her boyfriend, Will) and strongly dislikes what she doesn't (mess, change, her boss drinking out of her mug). Her life runs in a pleasing, predictable order…until now. Then, something truly unexpected happens: Cassie discovers she can go back and change the past. One small rewind at a time, Cassie attempts to fix the life she accidentally obliterated, but soon she'll discover she's trying to fix all the wrong things.

1985. Anita de Monte, a rising star in the art world, is found dead in New York City; her tragic death is the talk of the town. Until it isn’t. By 1998 Anita’s name has been all but forgotten—certainly by the time Raquel, a third-year art history student is preparing her final thesis. On College Hill, surrounded by privileged students whose futures are already paved out for them, Raquel feels like an outsider. Students of color, like her, are the minority there, and the pressure to work twice as hard for the same opportunities is no secret.

Sally Milz is a sketch writer for The Night Owls, a late-night live comedy show that airs every Saturday. With a couple of heartbreaks under her belt, she’s long abandoned the search for love, settling instead for the occasional hook-up, career success, and a close relationship with her stepfather to round out a satisfying life. But when Sally’s friend and fellow writer Danny Horst begins dating Annabel, a glamorous actress who guest-hosted the show, he joins the not-so-exclusive group of talented but average-looking and even dorky men at the show.

1950s Philadelphia: fifteen-year-old Ruby Pearsall is on track to becoming the first in her family to attend college. But a taboo love affair threatens to pull her back down into the poverty and desperation that has been passed on to her like a birthright. Eleanor Quarles arrives in Washington, DC, with ambition and secrets. When she meets the handsome William Pride at Howard University, they fall madly in love. But William hails from one of DC’s elite wealthy Black families, and his par­ents don’t let just anyone into their fold.

High-powered businesswoman Lana Rubicon has a lot to be proud of: her keen intelligence, impeccable taste, and the L.A. real estate empire she’s built. But when she finds herself trapped 300 miles north of the city, convalescing in a sleepy coastal town with her adult daughter Beth and teenage granddaughter Jack, Lana is stuck counting otters instead of square footage—and hoping that boredom won’t kill her before the cancer does.

Maya was a high school senior when her best friend, Aubrey, dropped dead in front of the enigmatic man named Frank whom they’d been spending time with all summer. Seven years later, Maya lives in Boston with a loving boyfriend and is kicking the secret addiction that has allowed her to cope with what happened years ago, the gaps in her memories, and the lost time that she can’t account for. But her past comes rushing back when she comes across a recent YouTube video in which a young woman suddenly keels over and dies in a diner while sitting across from none other than Frank.

The identity comes first: Evie Porter. Once she’s given a name and location by her mysterious boss Mr. Smith, she learns everything there is to know about the town and the people in it. Then the mark: Ryan Sumner. The last piece of the puzzle is the job. Evie isn’t privy to Mr. Smith’s real identity, but she knows this job will be different. Ryan has gotten under her skin, and she’s starting to envision a different sort of life for herself. But Evie can’t make any mistakes—especially after what happened last time.

Nisha Cantor lives the globetrotting life of the seriously wealthy, until her husband announces a divorce and cuts her off. Nisha is determined to hang onto her glamorous life. But in the meantime, she must scramble to cope--she doesn’t even have the shoes she was, until a moment ago, standing in. That’s because Sam Kemp—in the bleakest point of her life—has accidentally taken Nisha’s gym bag. But Sam hardly has time to worry about a lost gym bag—she’s struggling to keep herself and her family afloat.

William Waters grew up in a house silenced by tragedy, where his parents could hardly bear to look at him, much less love him—so when he meets the spirited and ambitious Julia Padavano in his freshman year of college, it’s as if the world has lit up around him. With Julia comes her family, as she and her three sisters are inseparable: Sylvie, the family’s dreamer, is happiest with her nose in a book; Cecelia is a free-spirited artist; and Emeline patiently takes care of them all.

In the spring of 2020, Lara’s three daughters return to the family's orchard in Northern Michigan. While picking cherries, they beg their mother to tell them the story of Peter Duke, a famous actor with whom she shared both a stage and a romance years before at a theater company called Tom Lake. As Lara recalls the past, her daughters examine their own lives and relationship with their mother, and are forced to reconsider the world and everything they thought they knew.

Hollis Shaw, creator of the popular food blog, Hungry with Hollis, is shocked when her heart surgeon husband, Matthew, is killed in a one-car accident on a snowy morning. The cracks in Hollis’s perfect life—her strained marriage and her complicated relationship with her daughter, Caroline—grow deeper. So when Hollis hears about something called a “Five-Star Weekend”—one woman organizes a trip for her best friend from each phase of her life: her teenage years, her twenties, her thirties, and midlife—she decides to host her own Five-Star Weekend on Nantucket.

Harriet and Wyn have been the perfect couple since they met in college—they go together like salt and pepper, honey and tea, lobster and rolls. Except, now—for reasons they’re still not discussing—they don’t. They broke up five months ago. And still haven’t told their best friends. Which is how they find themselves sharing a bedroom at the Maine cottage that has been their friend group’s yearly getaway for the last decade.

Rife with the indulgent pleasures of life among New York’s one-percenters, Pineapple Street is a smart, escapist novel that sparkles with wit. Full of recognizable, loveable—if fallible—characters, it’s about the peculiar unknowability of someone else’s family, the miles between the haves and have-nots, and the insanity of first love—all wrapped in a story that is a sheer delight.

In her twenties, Emma Blair marries her high school sweetheart, Jesse. They build a life for themselves, far away from the expectations of their parents and the people of their hometown in Massachusetts. They travel the world together, living life to the fullest and seizing every opportunity for adventure. On their first wedding anniversary, Jesse is on a helicopter over the Pacific when it goes missing. Just like that, Jesse is gone forever.

The Home Group is a glamorous collection of celebrity members' clubs dotted across the globe, where the rich and famous can party hard and then crash out in its five-star suites, far from the prying eyes of fans and the media.