Both her previous husbands having died, Khadijah Bint Khuwailid was a widow. She was known for her noble character, and the people of the Quraish would call her, “The Pious and Chaste One.”
She was also very wealthy; she would engage men to do business on her behalf. After she heard about the truthfulness and trustworthiness of Muhammad (peace be upon him), she proposed that he do business for her in Ash-Sham, promising to give him more than she gave to any other man who did business for her. He agreed and left Makkah in the company of Maisarah, Khadijah’s servant.
Muhammad (peace be upon him) made a lot of profit for Khadijah and she felt that her wealth was blessed more than ever before. Throughout the trip, Maisarah witnessed the wonderful character, nobility, and truthfulness of the Prophet (peace be upon him).
Based upon these reasons, she had a heart to heart discussion with her close friend Nafeesah Bint Munabbah, telling her about the positive feelings she was having about the Prophet (peace be upon him). Nafeesah went to the Prophet (peace be upon him) and proposed to him on behalf of Khadijah.
The Prophet (peace be upon him) was pleased with the proposal, but he nonetheless first went to his uncles to seek their advice; they all agreed that he should marry her.
And why shouldn’t he marry her, for she was the noblest woman among the Quraish; after her last husband had died, almost every Makkan chieftain proposed to her, and she refused them all.
And so shortly thereafter the Messenger of Allah (peace be upon him) married her. She was the first woman that the Prophet (peace be upon him) married, and he didn’t marry any other woman until she died. She gave birth to two of the Prophet’s sons and four daughters. The two sons were Al-Qasim and Abdullah.
Around the age that he was able to mount a riding animal, Al-Qasim died. Abdullah died as a child prior to his father’s prophet hood.
The daughters were Zainab, Ruqayyah, Umm Kulthoom, and Fatimah. They all embraced Islam, married, and migrated to Madina. When the Prophet (peace be upon him) married Khadijah, he was 25 years old and she was 40.
1. Trustworthiness and truthfulness are the two most important qualities of a successful businessman. They were the very two qualities that prompted Khadijah to ask the Prophet to do business on her behalf.
2. Allah decreed for the Prophet (peace be upon him) to marry the ideal wife who was both a suitable companion and a trusted counselor and helper. Khadijah helped the Prophet (peace be upon him) during difficult times, and participated alongside him in spreading the message of Islam.
One who invites others to the teachings of Islam is especially in need of a pious and good wife. Outside of the home, his days are filled with struggle, and he faces constant opposition from the enemies of Islam. He therefore is in dire need, within the home, of a partner who will comfort him and provide him with the strength and encouragement he needs to fulfill his religious duties.
3. The Prophet (peace be upon him) tasted the bitterness of losing his sons, just as previously in life, he tasted the bitterness of losing his parents. It was from the wisdom of Allah that none of his sons lived past their childhood. With their death, no one could then be tempted loving them to an extreme level and claiming prophethood for them. Furthermore, the early deaths of the Prophet’s children should serve as a comfort for those who aren’t blessed with sons, and for those who are blessed with sons but lose them at a very early age.
The death of the Prophet’s children was a form of tribulation and as the Prophet (peace be upon him) made it clear, no one is tested more severely than the Prophets.
Men who become leaders of nations turn to tyranny when their hearts are hard through a selfish and comfortable lifestyle. As for a leader who has experienced hardships and tests in life, and endures them with patience and forbearance, he is likely to then show compassion and sympathy to others who are afflicted with hardships.
4. In choosing Khadijah as a wife, the Prophet (peace be upon him) showed that he was primarily concerned with her nobility and character; after all, she was known in pre-Islamic days as “The Pure and Chaste One.”
Up until the age of 25, the Prophet (peace be upon him) lived a chaste life within a society that was replete with evil and ignorance, a society wherein one was free to have romantic and sexual counters with as many women as one desired.
Then when he did decide to marry, he married a woman who was almost twice his age. During the next 15 years of his life, there was no Shariah or set of laws to forbid him from engaging in extra-marital affairs, as did other members of the Quraish, yet he remained faithful to Khadijah, without even looking at any other woman, though there were many other women that were available.
The Prophet (peace be upon him) remained married to Khadijah alone until she died at the age of 65, at a time when the Prophet (peace be upon him) was himself approaching old age.
The story behind each marriage of his highlights the wisdom and wonderful character of the Prophet (peace be upon him).
Ref: Ali Muhammad As-Sallaabee, The Noble Life of the Prophet, Darussalam