The Details of the Question
Assalam-o-alaicom, I have two questions: 1. What are the rewards to marry a widow? 2.If a widow doesn't know wether she should marry or not, in this case what should she do? jazakallah khair.
The Answer

Dear Brother / Sister,

The religion of Islam gives great importance to virginity. Our Prophet (pbuh) said, “When you marry, prefer virgin girls because they are more soft-spoken; they can satisfy their husbands better and they will be content with fewer things." This hadith does not mean that Islam does not give importance to widows. There is no drawback for a bachelor man to marry a widow in terms of Islam. As a matter of fact, our Prophet’s first marriage was with a widow, Hazrat Khadija. Furthermore, all of the wives of our Prophet were widows except for Hazrat Aisha.
Some widows are superior to virgins in terms of ethics. It is better to act depending on the conditions and decide accordingly for marriage.
The decree about marriage is divided into parts as fard (obligatory), wajib, sunnah, haram (forbidden), makrooh (abominable) and mubah (lawfully permitted but not obligatory) depending on the condition of the person to be married:
1. If a person is sure to commit fornication if he does not marry, it is fard for him to marry if he can afford to pay mahr (marriage gift) and to look after his spouse.
2. If a person faces the risk of committing fornication if he does not marry, it is wajib for him to marry if he can afford to pay mahr and to look after his spouse. The majority of the scholars, except Hanafis, do not distinguish between fard and wajib (Ibnul-Humam, Fathul-Qadir, II, 342; al-Qasani, al-Badayi, II, 260 et al.).
3. If a person is sure to oppress his spouse, it is haram for him to marry. If a person faces the risk of both committing fornication and oppressing his spouse, the haram aspect is preferred. When halal and haram unite in an issue, haram is given superiority and it becomes necessary to avoid it. As a matter of fact, in a verse, the following is stated, " Let those who find not the wherewithal for marriage keep themselves chaste, until Allah gives them means out of His grace " (an-Noor, 24/33).
4. If a person is likely to oppress his spouse, it is makrooh for him to marry. (Mawsili, al-Ikhtiyar, III, 82).
5. If a person is moderate in terms of sexuality, it is sunnah for him to marry. The word moderate is used for a person who is not likely to commit fornication if he does not marry and who is not likely to oppress his spouse if he marries. The majority in a community are likely to belong to this group. The hadiths that recommend the youths who cannot afford to marry to fast and that warn the three sahaba who refrained from marrying are evidences for it. 
On the other hand, Hazrat Prophet and his Sahaba (companions) married and those who followed them continued that sunnah (marriage). That is the preferred opinion. (see al-Fatawa al-Hindiyya, I, 267).
According to Imam Shafi’, it is mubah to marry for the above-mentioned person. It is permissible for him to marry or to remain single. According to Imam Shafi’ it is better to spend one’s time worshipping and to try to learn knowledge than to marry. The evidence that he refers to is this: God Almighty praised the prophet Yahya (Jonah) using the following words: "...noble, chaste" (Aal-e Imran, 3/39). The word chaste in the verse means a person that does not have sexual intercourse although he can. If marriage were better, it would not be praised in the Quran. Most of the faqihs (scholars) said it was an application of a previous Shariah and that it did not bind Islam.
Another evidence of Imam Shafi’ is the following verse: " except for these, all others are lawful, provided ye seek (them in marriage) with gifts from your property,― desiring chastity, not lust " (an-Nisa, 4/24). If something is halal it means it is mubah. Those two words are synonymous. On the other hand, marriage benefits a person in terms of sex. It is not wajib for a person to do something that will benefit him. Therefore, marriage is one of the mubah acts like eating, drinking and shopping. (az-Zuhayli, al Fiqhu'l-Islami wa Adillatuh, Dimashq 1405/1985, VII, 33, 34; Ibn Hajar al-Asqalani, Bulughul-Maram min Adillatil-Ahkam, Trans. Ahmed Davudoğlu, İstanbul 1967, II, 228 et al.; Hamdi Döndüren, Delilleriyle İslâm Hukuku, İstanbul 1983, p. 183, 184).

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