Maya is a 23-year-old physics graduate who has recently returned to Texas after studying in Scotland. Following the traumatic loss of her parents during her adolescence, she grew up quickly and strives to prove her maturity. She is fiercely determined, highly intelligent, and occasionally anxious regarding high expectations, especially concerning her career choices.

Conor is the 38-year-old owner of a highly successful biotech firm and Eli's best friend. Raised by a wealthy, emotionally abusive father who exploited younger women, Conor is deeply cautious about power dynamics and age gaps in relationships. He often masks his caring nature behind a guarded exterior, believing that keeping his distance is the best way to protect those he loves.

Eli is Maya's older brother and the co-founder of a biotech investment firm. He unexpectedly became Maya's guardian after their parents died, a role that initially strained their bond but ultimately forged a strong family unit. He is deeply proud of his sister's academic achievements and focuses on ensuring his upcoming wedding to Rue goes smoothly.

Avery is an employee at the biotech firm and Conor's recent ex-girlfriend. She attends the destination wedding in Sicily and lives with lingering feelings for Conor. Despite the awkward dynamic, she is genuinely kind and shares several interests with Maya, including a love for heavily annotated travel guides.

Rue is Eli's fiancée and the reason for the gathering in Taormina. She is warm, perceptive, and initially shy, providing a stable and nonjudgmental presence for the friend group. She approaches the chaos of the destination wedding with a desire for emotional authenticity rather than superficial perfection.

Tamryn is Conor's stepmother and the owner of the Sicilian villa where the wedding takes place. She is close in age to Conor and was originally seduced by his wealthy father. Over time, she has grown from her past mistakes, taking control of her life and offering a model of flexibility and resilience to the younger women around her.

Minami is a co-founder of the biotech firm alongside Eli and Conor. She is a working mother who helps anchor the friend group. Having dated Conor in the past, she understands his emotional barriers intimately and acts as a benchmark for Maya's own maturity.

Nyota is a friend of Maya and a lively guest at the destination wedding. She is outspoken, eager for a fun summer fling, and frequently encourages Maya to act on her romantic desires rather than overthinking them.

Tisha is Rue's best friend and a member of the wedding party. She participates in the group's activities, including the bachelorette celebrations, offering support to the bride.

Hans is a young man close to Maya's age who meets her during a group activity. Understanding her situation, he amiably agrees to pretend to flirt with her in order to incite jealousy from afar.

Maya's former college boyfriend in Scotland. His infidelity and subsequent refusal to take responsibility for his actions serve as the catalyst that initially drives Maya to seek comfort and assistance from Conor.

A wealthy millionaire who frequently uses his money to seduce much younger women, including Tamryn. Though not physically present at the wedding, his manipulative legacy casts a long shadow over his son's approach to romance.