In the suburbs of Boston, Massachusetts, the Bella household prepares for youngest daughter Jan Bella’s wedding. After the ceremony, Renata Bella, the bride’s unmarried older sister, endures being teased by relatives. She becomes tearful when her father, Joe Bella, sings a love song in honor of the newly married couple. Later, Renata pressures her boyfriend Rob to ask her to be his wife, but he reveals he has no intention of ever marrying her. A heartbroken Renata seeks solace from her parents, who encourage her to pursue a job selling condominium timeshares in the tropics. Renata travels to a Caribbean island to learn the sales trade, and while walking on the beach one evening, she notices a dapper older man staring out to sea. The next day, Renata discovers that the man, Sam Sharpe, is the company’s top-ranked salesperson, and she conspires to have lunch with him. At sunset, the smooth-talking Sam invites the love-struck woman to New York City, where he lives, but Renata declines the invitation. Sam escorts her to her family home outside Boston in his limousine. Renata’s parents, Joe and Marilyn, are skeptical of their daughter’s interest in the man, whose lavish lifestyle contrasts with their own. However, they welcome him into their home. That night, Sam and Renata drink and talk late into the night, keeping Joe and Marilyn awake. Joe reprimands his daughter, and Renata expresses frustration at her parents’ inability to recognize that Sam makes her happy. She reminds them how depressed she felt after being rejected by Rob. The next day, Sam takes Renata into Boston, where he buys her jewelry and an expensive new wardrobe. As they drive home, he again asks Renata to live with him in New York City, but Renata, a Bostonian at heart, cannot accept his proposal. Undeterred, Sam declares he will move his business from New York to Boston. Meanwhile, at the Bella residence, Joe and Marilyn discuss Sam’s intentions toward their daughter, disagreeing about the sincerity of his actions. That night, the family gathers to celebrate Joe’s birthday, and Sam surprises Joe with the “gift” of a belly dancer. Newlyweds Jan Bella and her husband, Peter, arrive late to the party, and are stunned to see the entire Bella clan dancing through the house. Renata introduces the exuberant Sam to her sister, who makes no effort to conceal her disapproval. The next day, Renata discovers that her sister, Jan, has lingering feelings for their neighbor, Jim Redstone, with whom she had a brief affair before her wedding day. When Sam takes the Bella family to a nearby skating pond, the two sisters argue over each other’s romantic choices. That night, Jan wakes her parents, reminding them that no one knows anything about Sam’s private life. Joe placates his youngest child by agreeing to look into Sam’s background. Sometime later, the Bellas attend the hastily planned wedding of their neighbor, Jim, and a woman named “Honey Beach.” During the ceremony, Sam and Renata mimic the minister, whispering wedding vows to each other, and at the reception, they announce their engagement. Months later, Renata marries Sam. At the wedding reception, she overhears her father telling Jan that he still does not approve of Sam. However, the patriarch sets aside his bias and sings a romantic song in honor of the newlyweds. In the months that follow, Renata is conflicted: she loves Sam, but knows that her father has reservations about the man’s boisterous personality. At a memorial dinner for Joe’s deceased mother, Sam’s good intentions upset the entire Bella family, including a pregnant Renata. Later, Sam apologizes to his wife, and the two look forward to becoming parents. When Renata gives birth to a baby girl, the Bella family tentatively reconciles with Sam. However, while making plans for the baby’s baptism, the family erupts in disagreement, and Renata’s parents declare that Sam is no longer welcome in their house. Renata defends her husband’s extravagant ways and tells her family they are not welcome at the baptism. However, the family insists on attending. In the middle of the baptism, Sam suffers a heart attack. Several months later, the Bella family nervously anticipates Sam and Renata’s arrival at Christmas dinner. Although Sam is physically weak, he has lost none of his enthusiasm for living life to its fullest. Sam and Renata visit the skating pond with their baby daughter, and a wheelchair-bound Sam watches Renata glide across the ice. When Renata returns to her husband, she discovers he has died. On the day of Sam’s funeral, a stoic Renata proclaims she had the time of her life with Sam. A supportive Joe and Marilyn join their daughter in the limousine, which drives “once around” a traffic circle in tribute to Sam.