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After attending the dedication of the children's home she has endowed, elderly philanthropist Lydia Macmillan receives a visit from Dr. Michael Fitzpatrick, a former suitor whom she has not seen in nearly forty years. Lydia and Michael reminisce about the past, recalling the three other loves of Lydia's youth: college football star Bob Willard, musician Frank Audry, and Richard Mason, a seafaring adventurer. Agreeing to put their differences behind them, Lydia accepts Michael's invitation to tea, and when she arrives at his apartment a few days later, she is shocked, then delighted, to find Bob and Frank waiting for her with Michael. As they catch up on one another's lives, the conversation turns to Lydia's rejection of their marriage proposals. When asked why she refused to marry, Lydia cryptically responds that she truly loved only one man, Richard Mason. In answer to the men's queries, Lydia agrees to delve into her past to help the disappointed suitors understand her motivations and desires, beginning with the day in 1897 when she first met Michael: Lydia was reared in Boston by her wealthy grandmother, a crusty, but kind, dowager suffering from a severe case of hypochondria. While preparing for her first charity ball, the vivacious and stubborn young Lydia argues with her grandmother over her revealing ball gown, but the conflict is interrupted when the butler, James Fitzpatrick, proudly ushers in his handsome son Michael, who has just graduated from medical school. Michael's warmth and professionalism charm Granny, who immediately hires him on as the family physician, while Lydia talks him into buying a ticket to the ball. At the dance, the smitten Michael is disappointed to discover that Lydia's heart belongs to Yale football hero Bob Willard. Later, Lydia brings Bob home to meet Granny, but Granny disapproves of his drunken and foolish behavior and orders Lydia to stop seeing him. Lydia makes plans to elope with Bob to the nearby hamlet of Quincy and goes to Michael for help with carrying out the scheme, but Michael instead arranges for the justice of the peace to be called away that evening. Their plans disrupted, Bob and Lydia return to Boston to eat the wedding dinner Bob has ordered for them at a local hotel. After Bob drinks too much champagne and makes a pass at her, Lydia, sobbing, flees the hotel and refuses to see Bob again. In the present, Bob, now a nightclub owner, declares to the others with great shame that he has been repenting his actions for the last forty years, but Lydia reminds him that they were both equally foolish. Next, Lydia remembers the day when, shortly after the declaration of the Spanish American War, she accompanied Michael, who had enlisted, to the docks to bid him farewell. As the ship pulled out, Richard Mason, who had offered Lydia assistance on the night she left Bob, waved to her, but Lydia did not yet know the handsome stranger's name. When Michael asks if Richard was the man who changed Lydia's life, Lydia replies that it was not Richard, but Johnny, a blind boy she met that day, who determined the course of her future: After seeing the poverty and degradation in which Johnny lives, Lydia establishes a school for blind children. Hearing of her success with the children, the famous concert pianist Frank Audry, who unknown to the public is almost completely blind, arrives at the school to offer his services as a music teacher. Frank falls in love with Lydia, and Michael returns safely from the war, but Lydia nonetheless announces her intention to remain single so that she can devote herself to her work. However, Lydia changes her mind after she finally meets Richard and dances with him at a ball. At this point, Lydia breaks off her story, but at the men's urging she agrees to continue, expressing her desire to confess her "sin": Telling Granny that she must travel to New York on business, Lydia leaves Boston with Richard and heads for Macmillansport, the desolate and windswept ancestral home of the Macmillan family. After two passion-filled weeks together, Richard departs, leaving behind a note stating that he must settle another woman's "claim" on him and promising to return to marry Lydia. As Lydia is about to give up hope, she receives a ring from Richard and a note asking her to meet him in a Boston church on New Year's Eve for a midnight wedding. Lydia waits alone for hours in her wedding gown, but Richard never arrives. As the months pass, Lydia remains haunted by the memory of Richard, but keeps the love affair a secret. Frank, realizing that Lydia will never be his wife, leaves the school to pursue a career as a composer. Although Michael senses that Lydia loves another, he proposes marriage, and Lydia, craving stability, accepts. However, their happiness proves fleeting when Granny, in the act of toasting the couple, suffers a seizure and dies. Devastated, Lydia goes to Macmillansport in an attempt to free herself of her desperate love for Richard. Unsuccessful, she breaks off her engagement to Michael and spends the next forty years working with the blind. As Lydia ends her story, Michael's butler announces the arrival of Capt. Richard Mason. Lydia is overcome with emotion, but it soon becomes apparent that Richard neither recognizes nor remembers her. Lydia declares to Michael that the crumbling of her illusions about her love affair with Richard represent the "perfect punishment," and she sadly remarks that none of the four men ever really knew her. When Michael asks who the real Lydia was, Lydia responds that there never existed any one true Lydia. Rather, like all women, she was a mass of contradictions, representing different things to different people.