Once upon a time, Ramona Riley was a student at a prestigious art school, with dreams of landing in Hollywood as a costume designer to the stars. But after her father’s car accident, she had to quit and return to her small New Hampshire town, Clover Lake, to help take care of her younger sister. Twelve years later, Ramona is still working at the town’s café, all but given up on her dream. But when a big-budget romantic comedy comes to Clover Lake to film, she wonders if this could be her chance.

Elsie Hoffman has been engaged to her college boyfriend for a year and a half. Ginny Holtz has been in love with Elsie for almost a decade and a half. When Elsie discovers her fiancé already planned their wedding and honeymoon as a surprise and she’s expected to be in a white dress in seven days, she swiftly realizes she’s let herself become too comfortable with a future she never wanted. She breaks things off, and a week later is on a plane to the Caribbean for her non-refundable honeymoon with her best friend Ginny instead.

Harper Reid’s summer is not off to a great start. After the death of her grandpa, she moves across the country, leaving her friends and Dungeons & Dragons group behind. She wasn’t exactly planning to start her senior year on the farm where she spent her childhood summers, but running into Ollie Shifflet—former best friend and first crush—makes things much better. When Harper discovers Ollie and her friends are starting a new D&D campaign, she quickly joins the group. As Harper and Ollie reconnect in the real world, romantic tension begins to build.

June is the star pitcher of her elite club baseball team—with an ego to match—and she's a shoo-in to be recruited at the college level, like her parents have always envisioned. That is, if she can play through an overuse injury that has recently gone from bad to worse. Ivy isn't just reffing to pay off her athletic fees or make some extra cash on the side. She wants to someday officiate at the professional level, even if her parents would rather she go to college instead.

It's been five years since Charlotte Donovan was ditched at the altar by her ex-fiancée, and she’s doing more than okay. Sure, her single mother never checks in, but she has her strings ensemble, the Rosalind Quartet, and her life in New York is a dream come true. As the holidays draw near, her ensemble mate Sloane persuades Charlotte and the rest of the quartet to spend Christmas with her family in Colorado. But when Charlotte arrives, she discovers that Sloane’s sister Adele also brought a friend home—and that friend is none other than her ex, Brighton.