When my uncle died. I was ten years old, and it was the day of my elementary school graduation. I was told that he was going to survive whatever cancer he had and that he was going to be a great father to his son. Learning that he died out of the blue was really hard on a ten year old .
I feel your pain. My dad died when I was very young. I'm not sure if at that time whether or not I could fully understand what had happened, but it left a huge gash in me as I grew up. I've been told that I had depression so bad that I had to be sent to doctors. It didn't help that my family decided to cut off contact with my father's side. I grew up feeling so alone and unloved.
Probably when my great-grandma died. I watched the first Pokemon movie with her, and her favorite color was purple. It was so hard on me that I tried to stop thinking about Pokemon and the color purple, because they both reminded me of her. I was told that she would survive her heart surgery, and I wasn't allowed to visit her in the hospital before she died or even go to her funeral (I was 12 at the time). My mom kept telling me to pray for her after she died (which is something I hate to do, but I loved her so much that I prayed anyway, even though it made me uncomfortable). I think this was my "I am not a Christian" wakeup call, although I didn't come out to myself as an agnostic until I was 14 (I didn't know what that word meant until then). Afterwards, I felt extremely guilty, since she was an Irish Catholic, and I felt like I was spitting on her grave (This is another reason why I tried to convince myself that I was an aro-ace at age 15. I thought being asexual was more moral, and although she was never homophobic, and I highly doubt the existance of afterlife, I felt a lesbian identity would dishonor her memory). The most I've cried since then was after I told my best friend (who lives on the otherside of the country) about my feelings for her (this was in late May). I immidiately felt like some kind of dirty whore for feeling that way, and I've been going out of my way to avoid her on Facebook/Skype. I've had to accept the fact that I will most likely never fall in love again. I'm a very emotional person, and I can only fall in love with a woman who I've connected to 100% on a platonic level.
When my uncle died it hurt so much. I visited him in the hospital right before he died. He looked kinda gray. Then my mom got the phone call. When I saw him in the casket I broke down in tears. My grandmother was flipping out and a emotional wreck. But after that we celebrated his life.
The hardest I've cried was about two years ago when I found out I had gender dysphoria. I was just folding laundry and thinking about how different my life would have been if I was born male, and then it hit me. The pain hurt more than anything I had ever felt. That Summer, I learned that sometimes emotional pain can hurt as bad or more than any physical pain.
It was at camp, one based on leadership and acceptance. I found myself there and came out as bi to everyone, but I've really matured since then. Anyways, it was during this activity where we sort of looped around and held everybody's hands and looked into the person's eyes and basically told them how we felt with our expression and this one guy who came out as gay was absolutely bawling and I had already been crying but his sobs absolutely broke my heart and I felt his pain...I probably cried more when I had to leave because they were the only ones who knew about me at the time.