Penelope Campbell, an English teacher with a penchant for summer visits to her grandmother, Dot, finds herself at a unique crossroads this year. While Dot is eager to set her up with every single bachelor in town, Penelope's path is irrevocably intertwined with Jason Hanfrey, her childhood sweetheart and the man who remains as handsome and captivating as ever. Their reunion is bittersweet, filled with the familiar awkwardness that only time can bring. However, the conversation soon takes an unexpected turn when it drifts to Jason's grandmother, Sophie, a woman who has always harbored a special place in Jason's heart. In a bid to avoid their grandmothers' persistent attempts at matchmaking, the couple decides to play along with a mock date. But can the warmth and chemistry that once defined their relationship survive this new arrangement? As the summer unfolds, Penelope and Jason must navigate the delicate balance between their past and present, and discover if true love can bloom amidst the constraints of family expectations and societal norms.