Answered by Shaykh Yusuf Weltch
I started practicing Islam seriously for 4/5 years. Before that, I was a simple cultural Muslim who only lived by the Muslim identity and went to Islamic social gatherings. Thus, I lied a lot to everyone, including myself, about fasting. I didn’t fast (while saying I fasted); I think I said I fasted multiple times but then just broke it deliberately because I didn’t consider it as something serious and was just totally heedless and didn’t understand the implications of breaking the fast and just did whatever was convenient for me.
I am scared of this behavior and did tawba, but I think I need to do kaffara, but how much? I did it multiple times for multiple years and can’t estimate it.
In the Name of Allah, the Most Merciful and Compassionate
The fasts that you have missed since reaching puberty are obligatory (fard) to makeup. However, for many reasons, expiation is not due for not fasting. Consider the following ruling:
Expiation, on top of making up the fast, is due when a fast is deliberately broken by intentionally eating, drinking, or having intercourse during the day of a fast that one intended to perform from the previous night. [Maydani, al-Lubab fi Sharh al-Kitab]
In your scenario/s, it is highly unlikely that you had strong resolve (intention) to fast the day before breaking that fast. [Ibid.]
Hope this helps
Allah knows best
[Shaykh] Yusuf Weltch
Checked and Approved by Shaykh Faraz Rabbani
Shaykh Yusuf Weltch is a teacher of Arabic, Islamic law, and spirituality. After accepting Islam in 2008, he then completed four years at the Darul Uloom seminary in New York where he studied Arabic and the traditional sciences. He then traveled to Tarim, Yemen, where he stayed for three years studying in Dar Al-Mustafa under some of the greatest scholars of our time, including Habib Umar Bin Hafiz, Habib Kadhim al-Saqqaf, and Shaykh Umar al-Khatib. In Tarim, Shaykh Yusuf completed the memorization of the Qur’an and studied beliefs, legal methodology, hadith methodology, Qur’anic exegesis, Islamic history, and a number of texts on spirituality. He joined the SeekersGuidance faculty in the summer of 2019.