Khadija RA was a wealthy woman of Makkah. After Muhammad ﷺ led her trading journey to Bosra with great success, it was she who began the move towards marriage.
In one version, she confided in an elderly servant named Nafisa. Nafisa went to him and asked why he did not marry. He smiled and said, "Who would marry me? I am an orphan and I am poor." Nafisa asked what he would say if Khadija wanted to marry him. He fell silent, then said, "Why would she want me?" He had not said no, and Nafisa took that as a sign of his interest.
The reports differ on who gave Khadija RA in marriage. Ibn Ishaq says that the Prophet ﷺ's uncle Hamzah RA went with him to her father, Khuwaylid ibn Asad, who married her to him. Other reports say her guardian was her uncle, Amr ibn Asad. Sheikh Yasir Qadhi calls this second version the more authentic one.
In that version, recorded by Ibn Faris, the Prophet ﷺ came with his uncle Abu Talib, who gave the formal address. Abu Talib praised Allah and the noble line of the Quraysh, the keepers of the Ka'bah. Then he proposed on his nephew's behalf, with a dowry of 12 uqiyyah and a nash of silver. Amr ibn Asad accepted on the spot. Ibn Hisham gives the dowry differently, as twenty young she-camels.
One narration, with a very weak chain, claims that Khadija RA's father opposed the match and was made drunk so the marriage could go ahead. Ibn Hajar and others point out that this cannot be true, because her father had died long before.
Khadija RA had been married twice before, first to Atiq ibn Abid al-Makhzumi and then to Abu Hala al-Tamimi. She had children by both. Ibn Hisham names Hind and Zaynab as her children by Abu Hala, and some reports also name a son, Hala ibn Abi Hala.