I think the worst day of my life was when I was in mesivta and I masturbated on yom kippur. I think it was a huge factor in me losing a handle on my yiddishkeit for awhile; I struggled to remain observant for many years, and still don't have the same spark I used to have.

I wonder if others have had similar experiences.

I remember one year when I did that, I think the worst part for me is that I was worried that I had broken YK by using an ointment. I wasn't paying attention to the masturbation persay, but rather the issur.... Thats a hard memory to think about.

hi there i understand where your coming from and you feel bad about it. but its not true at all hashem is the same every day of the year and so are you . you could do teshuvah for that any other day of the year too . im sure its not what u wanted to happen and not planning to do it ever again and say this to hashem (viduy)and thats the perfect teshuvah and then yom kippur comes and cleans you from the dirt but teshuvah is now. chazak . remember its the y"h thats trying to put you down keep strong and get ready for a fresh new year

No i never masturbated on Y"K but I acted out, the day after R"H and I totally identify with feeling bad, dirty, worthless etc and the feeling of despondency, yiush and maybe even entertaining suicidal thoughts.

Today I accept that these feelings are my imagination and how I view myself, and not the reality (The reality is that HaShem's love for us is unconditional). I also admit powerlessness over these feelings because even if I am aware that they are irrational, it ain't gonna help, the feelings are more powerful than me, and I ask HaShem to help me accept myself and restore me to sanity.