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The question

What should one do who has broken many oaths numerous times and does not know their number, and wishes to make expiation, but cannot distinguish between the poor and the deceptive, and is a student who does not possess sufficient money to pay all the expiations at once? And can he pay the value of the food in money, or fast three days for each broken oath?

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Source: FtawySummarized from the full answer at Ftawy · imported Sep 2, 20262 min readAlso available in العربية
The answer

A Muslim should not swear by Allah frequently, based on the verse: ﴿And do not make [your oath by] Allah an excuse against being righteous﴾ [Al-Baqarah: 224] and His saying: ﴿And do not obey every [worthless] habitual swearer﴾ [Al-Qalam: 10].

If one breaks multiple oaths, and these oaths were repeated for the same thing, then there is only one expiation. However, if they were for multiple things, then each oath broken requires a separate expiation, contrary to some scholars who hold that one expiation suffices if all oaths are broken before any expiation is offered for them.

Oaths are divided into three types: 1. Lapse Oath (Yamin al-Laghw): This is an oath made unintentionally, such as saying "No, by Allah" in the course of conversation. There is no expiation for it. 2. Binding Oath (Yamin al-Mun'aqidah): This is an oath to do or refrain from doing something in the future. Expiation becomes obligatory upon breaking it. 3. Perjured Oath (Yamin al-Ghamus): This is swearing falsely about something in the past or present. It immerses the one who takes it in sin. According to the preponderant opinion, there is no expiation for it; rather, sincere repentance (Tawbah Nasuh) is obligatory.

The expiation for an oath is to feed ten poor people with an average meal, or to clothe them, or to free a believing slave. If one cannot find any of these, then he must fast for three consecutive days. It is permissible to distribute the feeding over several days to the same poor person.

It appears that whoever only possesses his daily sustenance is only obligated to fast. So, whoever is able to feed, clothe, or free a slave, must choose one of these. But whoever is in straitened circumstances and does not possess more than his and his dependents' daily sustenance for a day and a night, moves to fasting.

Summarized from the full answer at Ftawy · imported

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Ftawy
Original fatwa ID
113257
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Source text, unreviewed
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