Evening
The film alternates between two time periods, the 1950s and the present, in which a dying Ann Grant Lord (Vanessa Redgrave) reflects on her past. Her confusing comments about people she never mentioned before leave her daughters, reserved Constance (Natasha Richardson) and restless Nina (Toni Collette), wondering if their mother is delusional.
As a young woman in her early twenties, cabaret singer Ann (Claire Danes) arrives at the spacious Newport, Rhode Island, home of her best friend Lila Wittenborn (Mamie Gummer), who is on the verge of getting married to Karl Ross (Timothy Kiefer). Lila's brother (and Ann's college friend) Buddy (Hugh Dancy) introduces her to Harris Arden (Patrick Wilson), a young doctor and the son of a former family servant. Buddy tells Ann his sister always has adored Harris, and expresses his concern that she's marrying another man out of a sense of duty rather than love. Inebriated, Buddy passes out, and as Ann and Harris chat they find themselves bonding.
On Lila's wedding day, she confesses to Ann that she confronted Harris with her feelings for him and he rebuffed her, so she goes along with the ceremony as planned and marries Karl. At the reception, at Lila's request, Ann sings a song and is joined on stage by Harris. Afterwards Buddy, drunk again, confronts the two about their growing closeness. Then he unexpectedly kisses Harris. As Lila prepares to depart with her new husband, Ann offers to take the bride away with her, but Lila refuses and leaves for her honeymoon.
Buddy admits to Ann he's had a crush on Harris since his childhood, though he also claims not to be "that way" - he denies that this would be okay as Ann assures him. He then changes the subject, confessing he has loved Ann ever since their college days, offering as proof a note she once sent him he has kept in his pocket ever since. Ann is unconvinced.
By the sea the younger guests dance drunkenly and dive into the sea from a clifftop: Buddy joins in but fails to surface, prompting a panicked search. When Buddy reappears at the top of the cliff, Ann expresses her anger at the prank and berates Buddy for repressing his sexual orientation and building her up as his true love. She storms off and she and Harris slip off to his secret hideaway, where the two make love.
Buddy, in search of the couple, stumbles into the road and is hit by a car. His friends find him, but too late to save his life. The following morning, Ann and Harris, oblivious to what transpired the night before, jokingly consider sailing away, but at the Wittenborn house they hear the tragic news of Buddy's death.
In the present day, Lila (Meryl Streep) arrives at Ann's bedside to comfort her and reminisce. Ann recalls a day when she ran into Harris in the street in New York City. By then she had one daughter and was on the verge of moving to Los Angeles, and he was married with a son. He intimated he still loved her before the two exchanged cordial goodbyes.
As Lila leaves, she tells Nina about Harris and reassures her that her mother did not make any mistakes in her life. Nina sits with Ann, who encourages her daughter to have a happy life. Nina finally musters the courage to tell her boyfriend Luc she is pregnant with their child. An ecstatic Luc proudly announces the news to Constance and promises he always will be there for Nina. Their joy is interrupted by Ann's nurse, who urges the women to rush to their mother's bedside to bid her farewell.
romantic, flashback