In 595, Khadija needed an agent for a transaction in Syria. Abu Talib ibn 'Abd al-Muttalib recommended her distant cousin Muhammad ibn Abdullah. The experience that Muhammad held working with caravans in his uncle Abu Talib's family business had earned him the honorific titles Al-Sadiq (the truthful) and Al-Amin (the trustworthy, the honest).[7] Khadija hired Muhammad, who was then 25 years old, sending word through her kinsman Khazimah ibn Hakim that she would pay double her usual commission.[citation needed]
She sent one of her servants, Maysarah, to assist him. Upon returning, Maysara gave accounts of the honorable way that Muhammad had conducted his business, with the result that he brought back twice as much profit as Khadija had expected. Maysarah also relayed that on the return journey, Muhammad had stopped to rest under a tree. A passing monk, Nestora, informed Maysara that, "None but a prophet ever sat beneath this tree."[8] Maysara also claimed that while he stood near Muhammad as he slept, he had seen two angels standing above Muhammad creating a cloud to protect him from the heat and glare of the sun.[5]
Khadija then consulted her cousin Waraqah ibn Nawfal ibn Asad ibn 'Abdu'l-'Uzza.[8] Waraqah said that if what Maysara had seen was true, then Muhammad was in fact the prophet of the people who was already expected. It is also said Khadijah had a dream in which the sun descended from the sky into her courtyard, fully illuminating her home.[5] Her cousin Waraqah told her not to be alarmed, for the sun was an indication that the Prophet would grace her home.[5] At this, Khadija considered proposing marriage to her agent.[9] Many wealthy Quraysh men had already asked for her hand in marriage,[5] but all had been refused.
Khadija entrusted a friend named Nafisa to approach Muhammad and ask if he would consider marrying.[10] At first Muhammad was hesitant because he had no money to support a wife. Nafisa then asked if he would consider marriage to a woman who had the means to provide for herself.[11] Muhammad agreed to come meet with Khadija, and after this meeting they agreed to consult with their uncles. The uncles agreed to the marriage, and Muhammad's uncles accompanied him to make a formal proposal to Khadija