How does Islam regard a man who has not married before marrying a widow with children?

Dear Brother / Sister,

There is no drawback to a man who has not married before marrying a widow with children. Besides, the state of the woman he will marry is important. It might sometimes be better to marry a widow. The parties are to decide about it. As a matter of fact, when the Prophet (pbuh) was 25 years old, he married Hz. Khadijah, who was a widow aged 40. All of his other wives except Hz. Aisha were widows.  

However, a man can prefer an unmarried woman if possible. However, this is an advice; it is not binding.

When I got married, the Messenger of Allah (pbuh) asked me,
"What kind of a woman did you marry (a widow or a virgin)?" I said,
"I married a widow." He said,
"Why did you not marry a virgin? You would play with her and she would play with you." [Bukhari, Nikah 10; Muslim, Rada 54, (715); Abu Dawud, Nikah 3, (2048); Tirmidhi, Nikah 4, 13 (1086, 1100); Nasai, Nikah 6, 10 (6, 61-65)]

Uwaym Ibn Saida narrates:

"The Messenger of Allah (pbuh) said,

"Marry virgin girls. Their mouths are sweeter, they are more fertile and they would show consent to less."

The sweetness of their mouth is understood as follows: "They speak decently since they are shy; they do not utter offensive and bad words against their husbands." The hadith praises the attribute of fertility of women.

It is said that what is meant by a woman showing consent to less can be "related to material needs like eating, drinking and garments as well as sexual intercourse." The following is also stated: "A widow may have had plenty of material things from her previous husband. When she cannot find the same things or better things from her new husband, unpleasantness may occur." (Prof. Dr. İbrahim Canan, Kütüb-ü Sitte Şerhi)

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