There were about nine significant women in Rizal's life. They were: Segunda Katigbak, Leonor Valenzuela, Leonor Rivera, Consuelo Ortega, O-Sei San, "Gettie" Beckette, Nelly Boustead, Suzanne Jacoby, and Josephine Bracken.
Segunda Katigbak and Leonor Valenzuela:
Segunda Katigbak is considered to be Rizal's first puppy love, but she became engaged to a townmate of theirs - Manuel Luz. After Segunda came Leonor Valenzuela who came from Pagsanjan. Rizal would send her love letters written with invisible ink, which could only be read by way of lamp or candle light. Unfortunately, he had to say goodbye to her on the night before he left for Spain.
Leonor Rivera was Rizal's love for 11 years and she was the reason he tried not to fall in love with other women during his travels. But, due to Rizal's being a Propagandist and owing to the fact that he was the cause of many political problems in Calamba, Leonor's mother disapproved of the relationship. It is known that Rizal sent many letters and notes to Leonor, all of which her mother hid and never gave to her. This caused Leonor to believe that Rizal no longer had any feelings for her and she decided to agree to marrying a man of her mother's choosing - the Englishman Henry Kipping.
During his stay in Madrid, Rizal and some fellow Filipino's would visit the home of Don Pablo Ortiga. They went there to visit the Don's daughters, but more specifically, Rizal went there to visit Consuela, who was considered to be the prettiest among Don Pablo's daughters. Consuela fell in love with Rizal and he even wrote a poem for her called A LA SENORITA C.O. y R. which became one of his best poems. Yet, keeping in mind that he was loyal to Leonor Rivera, he backed out before the relationship could get any more serious. Also, he knew that his friend - Eduardo de Lete – was in love with Consuela and he did not wish to destroy their friendship over a girl.
O Sei San:
During his stay in Japan, Rizal fell in love with his guide, interpreter, and teacher in the Japanese language. It is said that if Rizal did not have a personal mission to accomplish, he would have married O-Sei San and lived in Japan for good.
In London, while Rizal was working on his annotation of Morga's work, he stayed in the Beckette family house which was walking distance from the British Museum where Morga's work was displayed. The eldest of the Beckette sisters, Gertrude or "Gettie" as Rizal used to call her, fell in love with Rizal. He suddenly left for Paris though, in order to avoid the growing feelings between himself and Gettie. Before he left, he left Gettie a sculpture of the Beckette sisters.
After learning of Leonor Rivera's marriage to Henry Kipping, Rizal was able to go back to courting the other ladies. During his stay in Biarritz, Rizal stayed with the Boustead family, where he became friends with Eduardo Boustead's two pretty daughters. He would practice fencing with them at Juan Luna's studio. Antonio Luna, another frequent visitor to the Boustead residence, was trying to court Nelly but she was already infatuated with Rizal. This resulted in an ugly scene where Antonio said some bad words about Nelly while he was drunk at a Filipino hosted party in Madrid. Rizal then challenged him to a duel, but Antonio - after sobering up - realized his mistakes and apologized to Rizal and thus preventing rift among the unified Filipinos in Madrid. Unfortunately, Rizal and Nelly did not end up getting married because Rizal did not want to be converted to Protestant and Nelly's mother didn't want a poor man for ther daughter. The good thing is, they remained friends and parted as friends when Rizal left Europe.
Due to the high cost of living in Paris during the 1890's, Rizal moved to Brussels where he stayed in a boarding house owned by the Jacoby sisters. As time passed by, they fell in love but it was for nothing since Rizal ended up leaving Brussels, though she did write him while he was in Madrid.
While in Dapitan, late Feb 1895, Rizal met an 18 year old Irish girl. Josephine Bracken had blue eyes, brown hair and was a happy character. She was the adopted daughter of George Taufer, a man from Hong Kong seeking medical help from Rizal. It is said that Rizal was attracted to her physically, and that his loneliness had taken over and that it was better than to be in love again. Surprisingly, the Rizal sisters thought that Josephine was a spy for the friars and considered her a "threat to Rizal's security." In time, Rizal proposed to Josephine but she wasn't prepared to make such a big choice, since she still had to look after her blind father. Unfortunately, George Taufer's illness could not be treated so he went back to Hong Kong while Josephine stayed with Rizal's family in Manila. When she returned to Dapitan, Rizal tried to arrange for their marriage with Father Antonio Obach. the priest, however, wanted a retraction as a precondition to marrying them. Thus, Rizal took Josephine as his wife even without the Church's blessing, at the urging of his family and with her consent. She later gave birth to a stillborn, believed to be the result of some incidence, and this could have traumatized her.