After breaking off her engagement, 30-something Andi Cutrone yields New England to her ex and flees home to Long Island. There, she devotes her time to teaching in the writing program at Brooklyn University and overanalyzing her past failed relationships. But then she meets Devin, a male escort whose client list seems to include at least half of the accomplished women she knows. He is handsome, charismatic, and absolutely out of her league, but she can't deny he has a certain...something. And so Andi makes him a proposition: If he will teach her to shed her sexual inhibitions, she will teach him to be a writer.
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Four little words. That's all it took. Just four words to turn Andi Vanzant's world upside down. Until then, Andi thought her life was perfect: married to an adoring man, recently tenured at Northampton University, and a published author. But when her husband is killed by a drunk driver just blocks from their home, his death plunges Andi into a grief from which she cannot imagine ever surfacing. Her family and friends do their best to help her pick up the pieces, but nothing they do or say will ever bring back what Andi lost that night. Andi's widowed mother advocates stoicism, her best friend Maggie is frustrated that Andi is not trying harder to rally from her loss, and Andi's therapist encourages her to heal unresolved issues. Despite their efforts, she is resistant to any and all advice. When an unexpected reunion renews an old friendship, Andi sees signs of hope that someday she can be happy again. She begins to take tentative steps toward starting over, daring to live a life different from the one she'd always envisioned.
Andi and David have settled happily into Andi's Northampton home, but David wants more. He wants them to get married. But their discussion is put on hold when Wylie, a fifteen-year-old girl, shows up in their backyard, bearing news that takes David's mind off the future and sends it spiraling into the past. Reeling from David's news, Andi receives a startling announcement of her own, one that leads to a relationship with her estranged mother. As Andi and her mother get closer and Wylie weaves her way into their lives, Andi finds solace in an old comfort: her ex-fiancé.