Hallie is a mid-twenties tax accountant living in Omaha, Nebraska. Following a painful breakup with her long-term boyfriend, she enters a dormant phase she calls the "winter of her twenties" by taking on side jobs at a bar and a jewelry store. She is straightforward, fiercely loyal to her friends, and possesses a quick sense of humor. Seeking an authentic connection, she joins a dating app to find someone who will treat her as their favorite person.

Jack is a successful landscape architect who designs public spaces. He comes from a tight-knit Omaha family and firmly supports Chicago sports teams. Deeply unsettled by the lonely death of his bachelor uncle, Jack actively seeks a meaningful relationship to avoid a similar fate. He uses witty banter to connect with others while masking his deeper insecurities about being unwanted.

Olivia is Jack's younger sister who recently married his best friend, Colin. She experiences frequent accidents, such as getting her foot run over by a driver right before her honeymoon. She acts as a grounded sounding board for her brother's romantic life, actively intervening when she thinks he is making poor choices out of loneliness.

Ruthie is Hallie's eccentric roommate. She rides a motorcycle and participates in a secret fight club. Her unpredictable, chaotic lifestyle pushes Hallie to aggressively save money for a private apartment.

Ben is Hallie's former partner who serves as the best man in her sister Lillie's upcoming wedding. During their relationship, he expected Hallie to conform to his specific, polished lifestyle preferences. His past criticisms made Hallie feel like her natural personality was an embarrassment.

Colin is Jack's best friend and former roommate. He recently married Jack's sister, Olivia, transitioning from a friend to an official family member.

Chuck is Hallie's close friend and family relation. He is in a committed relationship and heavily encourages Hallie to join a dating app to find her own happiness. He provides practical advice and emotional support when she doubts herself.

Lillie is Hallie's younger sister. Growing up, Lillie was perceived as the messy sibling while Hallie had her life together. Her upcoming wedding in Vail, Colorado, creates a strict timeline for Hallie to secure a formal date.

Alex is a blond real estate agent who goes on several dates with Hallie. He plans elaborate, picturesque outings like dining in park igloos and expresses an intense early interest in forming a serious relationship with her.

Vanessa is Jack's former girlfriend. She breaks up with him publicly at an event because she feels he is rushing their relationship toward an unwanted engagement, setting off Jack's crisis of confidence.

Mack is Jack's late uncle. He spent his life as a bachelor and was known as the life of the party, but his poorly attended funeral deeply unsettled his nephew.

Will is Jack and Olivia's older brother. He shares his family's deep enthusiasm for Chicago sports teams and participates in their good-natured familial teasing.

Tigger is a fat, older tabby cat. Hallie adopts him to mark her fresh start in a new apartment, and he quickly becomes a fixture in her domestic life.

Jamie is Chuck's significant other. The stability of their relationship provides a successful model for what Hallie hopes to find on the dating app.

Allison is Hallie's high school friend. She bluntly points out that Hallie has transformed from a highly responsible person into a complete mess.