Praise be to Allah.
If someone swears an oath that he will not do something or that he will do it, and he swears that he will not break his oath or that he will not offer expiation or be forgiven for his oath, then he breaks his oath, then he must offer two expiations.
It says in Sharh Mukhtasar Khaleel by al-Khurashi (3/64): If someone swears an oath that he will not do a thing or that he will do it, then he swears that he will not break this oath, then he does break it, in that case he must offer expiation twice, once for breaking his oath and then for swearing that he would not break his oath but then he broke his oath. End quote.
Ad-Dardeer said in ash-Sharh as-Sagheer (2/217): … Or he swore that he would not do such and such, and he swore that he would not break his oath, then he broke it, such as if he said: By Allah, I shall not speak to Zayd and by Allah, I shall not break my oath, then he spoke to him. In that case he must offer two expiations, one for breaking his original oath and one for breaking his other oath. End quote.
You should understand that according to the view of the Hanbalis, the one who swears an oath – even if it has to do with many different things – then breaks that oath before offering expiation for any of those things must offer one expiation.
See: Kashshaaf al-Qinaa‘ (6/244).
So according to the view of the Hanbalis, you only have to offer one expiation, but to be on the safe side you can offer two expiations, following the view of the majority, unless that is too difficult for you.
You should understand that it is disliked (makrooh) to make oaths frequently, because Allah, may He be exalted, says (interpretation of the meaning):
{And do not obey every worthless habitual swearer} [al-Qalam 68:10].
This criticism of him indicates that his action is disliked, as Ibn Qudaamah (may Allah have mercy on him) said. "Al-Mughni (13/439)".
Allah knows best.
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