Annie is a 27-year-old flower shop owner living in the small town of Rome, Kentucky. The town views her as exceptionally innocent and pure, saddling her with the unwanted nickname "Angel Annie." In private, she reads steamy pirate romance novels and yearns for excitement that contradicts her public image. She struggles with people-pleasing and frequently suppresses her own needs to ensure her siblings remain happy.

Will is the highly skilled personal bodyguard for pop star Amelia Rae Rose. He frequently travels the world, chasing adventure and casual dates to avoid boredom and emotional introspection. His parents' volatile marriage left him with a deep aversion to long-term commitment. He agrees to act as a dating coach for Annie in exchange for borrowing her romance novels.

Amelia is a world-famous pop singer currently taking a break from the limelight in Kentucky. She is engaged to Noah Walker and quickly forms a tight bond with his younger sisters. Unlike the locals, Amelia views Annie without preconceived notions and actively acts as a matchmaker.

Noah is the eldest Walker sibling and runs The Pie Shop, a generational family business. He took on a parental role for his younger sisters following the tragic death of their parents when he was a child. He is currently engaged to Amelia and maintains a close, protective watch over his siblings.

Emily is a 29-year-old elementary school teacher and the eldest Walker sister. She acts as a fierce protector for Annie and often treats her more like a daughter than a sibling. Her intense fear of abandonment causes her to push her siblings to remain in their small hometown permanently.

Madison is the second-youngest Walker sibling. She works as a teacher to appease Emily but privately dreams of attending culinary school to become a professional cook. She possesses a bold personality and wild brown eyes, frequently clashing playfully with her family members.

Mabel owns the local inn and serves as a surrogate grandmother to the Walker siblings. She provides a nurturing space for the town's youth while staying heavily involved in local gossip. She uses her position to gently push Annie and Will toward recognizing their own feelings.

Silvie is the biological grandmother of the Walker siblings. She cared for them tirelessly after they were orphaned. She recently moved into an assisted-living facility after receiving an Alzheimer's diagnosis.

Charlotte is the late mother of the Walker siblings. She died in a tragic camping accident when Annie was a toddler. Her lifelong love of flowers inspired her youngest daughter's career path.

Ethan is Will's younger brother. He recently proposed to his girlfriend, choosing to take a chance on lasting love despite the traumatic, unstable childhood he shared with Will.

James is Noah's neighbor and friend. He frequents the town's local businesses and shows a quiet interest in Madison's life decisions.

Brandon is an attractive single veterinarian who recently moved to Rome. He asks Annie on a date and appears to check all the boxes for her ideal, stable partner.

John is a local bank teller known for his good looks. He takes Annie on a date but rudely abandons her after complaining about her personality over the phone to a friend.

Harriet is an elderly, talkative resident of Rome. She harbors an ongoing rivalry with Mabel and enjoys stirring up town business by organizing local petitions.

Phil owns the local hardware store. He takes a fatherly interest in Annie and openly warns outsiders to treat her with care.

Liv is Will's boss at the security agency. She manages his celebrity accounts and attempts to convince him to take a permanent post in Kentucky rather than moving to a political detail.

Gretchen is a beautiful woman who goes on a brief date with Will before his distraction regarding Annie cuts their evening short.

Hannah is Ethan's girlfriend of three months who recently accepted his marriage proposal.

Merritt is Noah's former fiancée. She prioritized her career over their relationship and cheated on him, making Noah deeply hesitant to trust outsiders.