Firstly: 

If a person swears many oaths and breaks them, and does not offer expiation, one of two scenarios must apply. 

1 – The vows were all to do with one thing, such as saying, “By Allah, I will not smoke,” then he breaks the oath and does not offer expiation for that. Then he swears again that he will not smoke, then he breaks the oath… in this case one expiation is required. 

2 – The oaths have to do with several actions, such as saying, “By Allah, I will not drink; by Allah, I will not wear (certain clothes); by Allah, I will not go to such and such a place,” then he breaks all those oaths. Does he have to offer one expiation or as many expiations as the oaths he swore and broke? There is a difference of opinion among the fuqaha’ (jurists) concerning this matter. The majority are of the view that he must offer several expiations, but the Hanbalis say that he only has to offer one expiation. 

The more correct view is that of the majority, because these were oaths to do several things, and breaking one of them does not mean that another is broken, they are not interconnected. 

Shaykh Ibn Baaz (may Allah have mercy on him) was asked: I am a young man and I swore to Allah more than three times that I would repent from a haram (unlawful) action. My question is: do I have to offer one expiation or three? And what is my expiation? 

He replied: You have to offer one expiation, which is feeding or clothing ten poor persons, or freeing a slave. Whoever cannot do that must fast for three days, because Allah, may He be glorified, says (interpretation of the meaning): 

“Allah will not punish you for what is unintentional in your oaths, but He will punish you for your deliberate oaths; for its expiation (a deliberate oath) feed ten Masaakeen (poor persons), on a scale of the average of that with which you feed your own families, or clothe them or manumit a slave. But whosoever cannot afford (that), then he should fast for three days. That is the expiation for the oaths when you have sworn. And protect your oaths (i.e. do not swear much). Thus Allah makes clear to you His Ayat (proofs, evidences, verses, lessons, signs, revelations, etc.) that you may be grateful” [5:89] 

This applies to every oath that is made to do one thing or to refrain from one thing; if the oath is sworn repeatedly, only one expiation is required, if he did not offer expiation the first time. But if he offered expiation the first time, then he repeated the oath, then he must offer another expiation if he breaks the oath. Similarly, if he repeated it a third time and had offered expiation the second time, he must offer a third expiation. 

But if he swore oaths to do several things or to refrain from several things, then he must offer expiation for each one, such as if he said, “By Allah I will not speak to so and so,” and “By Allah I will not eat food,” and “By Allah, I will not travel to such and such a place,” and “By Allah, I will speak to so and so” and “By Allah, I will hit him,” and so on. 

What must be done is to give each poor person half a saa’ (dry measure) of the local staple food, which is approximately one and a half kilograms. With regard to clothing, it should be what is sufficient for prayer, such as a thobe (robe) or a rida’ and izaar (upper and lower garment). If he gives them dinner or breakfast, that is sufficient, because of the general meaning of the verse quoted above. And Allah is the source of strength.  

End quote from Majmoo’ Fataawa al-Shaykh Ibn Baaz (23/145) 

Secondly: 

If the person asked about is suffering from waswaas, and he swore these oaths under the influence of that waswaas, without intending to do so or wanting to swear an oath, then he does not have to do anything. 

Shaykh Ibn ‘Uthaymeen (may Allah have mercy on him) said: If a person is suffering from waswaas, his divorce does not count as such if he utters the words of divorce, if it was not done intentionally, because this utterance of divorce was caused by the waswaas and was not intended, rather he was compelled to do it because of the strength of the waswaas and his lack of willpower to resist it. The Prophet (peace and blessings of Allah be upon him) said: “There is no divorce when one is compelled.” So the divorce does not count as such if he did not truly intend it willingly. This is something that he was compelled to do and did not intend or choose to do, so it does not count as a divorce. End quote from Fataawa Islamiyyah (3/277). 

If this applies to divorce, then it applies even more so to oaths, because the issue of marriage is more serious than the issue of oaths. 

And Allah knows best.