He broke oaths and does not remember how many they were; what should he do?
Question

I went through a period when I used to do something wrong, which was that if I was confused between two matters, I would swear that I would not do one of them so that I could escape this confusion, and sometimes I broke a lot of the oaths. There were many of them are of various types and I cannot remember how many they were. Now I want to offer expiation for them. How can I do that?.
Praise be to Allah.You are right in describing what you did as being wrong, because the Muslim should regard the matter of oaths as something serious and not make many of them. Allah condemns those who make oaths a great deal, as He says (interpretation of the meaning):
“And (O Muhammad (peace and blessings of Allah be upon him)) obey you not everyone Hallaaf Maheen (the one who swears much and is a liar or is worthless)” [al-Qalam 68:14]
“And make not Allah’s (Name) an excuse in your oaths against your doing good and acting piously, and making peace among mankind. And Allah is All-Hearer, All-Knower (i.e. do not swear much and if you have sworn against doing something good then give an expiation for the oath and do good)” [al-Baqarah 2:224]. 
Abu Bakr al-Jassaas said in Ahkaam al-Quran (1/483): It is as if the meaning is: Allah forbids you from swearing oaths a great deal and being disrspectful towards Allah, may He be exalted, because that is contrary to righteousness and piety; so be righteous and pious. End quote. 
The scholars have clearly stated that it is not right to swear oaths a great deal. Ibn Qudaamah said in al-Mughni (9/386): 
It is not right to be heedless in swearing by Allah (i.e., to do so a great deal), because Allah says (interpretation of the meaning):
“And (O Muhammad (peace and blessings of Allah be upon him)) obey you not everyone Hallaaf Maheen (the one who swears much and is a liar or is worthless)” [al-Qalam 68:14].
This is a criticism of it which implies that it is not right to do it. End quote. 
So long as you swore numerous oaths concerning various matters, you have to offer kafaarat yameen (expiation for breaking an oath) for everything that you swore to do and did not do. Ibn Qudaamah (may Allah have mercy on him) said in al-Mughni (9/406): If he swore oaths of various kinds, and said: By Allah I will not eat…, by Allah I will not drink…, by Allah I will not wear…, and he broke all these oaths, then he has to offer expiation for each oath. This is the view of the majority of the scholars. End quote. 
So you have to try hard to work out the number of oaths that you broke, and whatever you think is most likely the number of oaths that you swore and broke, you should offer expiation for them. This is what is stated in a fatwa of the scholars of the Standing Committee for Issuing Fatwas, as we have stated in the answer to question no. 34730 
And Allah knows best.