Concerning Khadijah:
Ibn Ishaq said: Khadijah bint Khuwaylid ibn Asad ibn ʿAbd al-ʿUzza ibn Qusay—who was one generation closer to Qusay than he, blessings and peace be upon him—was a woman of rank and wealth who engaged in trade. She used to hire men to conduct business with her capital, for Quraysh were merchants by profession. She therefore proposed to the Prophet, blessings and peace be upon him, that he take her goods to Syria, and she sent with him a boy named Maysarah.
He travelled to Syria and stopped to rest beneath a tree near a hermitage. The monk looked out toward Maysarah and asked, “Who is this man?” Maysarah replied, “A man from Quraysh.” The monk said, “No one has ever sat beneath this tree except a prophet.”
The Prophet, blessings and peace be upon him, then sold the merchandise, made a profit, and returned. According to what is claimed, whenever the heat grew intense Maysarah would see two angels shading him from the sun as he walked.
Al-Muhamili transmitted the story of the Prophet’s journey to Syria as a merchant through ʿAbd Allah ibn Shabib—who is weak—who said: “Abu Bakr ibn Shaybah narrated to us; ʿUmar ibn Abi Bakr al-ʿAdawi narrated to me; Ibn Shaybah narrated to me; ʿUmayrah bint ʿAbd Allah ibn Kaʿb ibn Malik narrated to me, from Umm Saʿd bint Saʿd ibn al-Rabiʿ, from Nafisah bint Munyah, the sister of Yaʿla, who said: ‘When the Messenger of Allah, blessings and peace be upon him, reached twenty-five years of age…’” He then recounted the entire episode at length, but it is a rejected hadith.
He continued: “When he returned to Mecca, Khadijah sold what he had brought and realized nearly double its value. Maysarah told her about the monk’s remark and about the two angels. She was an intelligent, decisive woman, so she sent word to him: ‘Cousin, I have become inclined toward you because of our kinship, your trustworthiness, your truthfulness, and the excellence of your character.’ She then offered herself to him. He relayed the matter to his uncles, and Hamzah, his uncle, accompanied him until …"