Top Opinion If I'm to be completely honest... I doubt I would even date someone who had been divorced 5 times nevermind marrying them. Once is fairly normal, twice... could be a coincidence, 3 times, a really shit deal... maybe. Five times tells me that there are probably some serious underlying issues that I do not have the time, patience or energy to deal with. No thank you. So here is goes...as a woman who has been married five times, it is easy to judge someone when you haven't lived their life. In my case my first marriage was at 15. I got pregnant and felt it was best to marry the father of my child, but at 15 you don't understand until death do us part. My second marriage was at 19. I was happy for the first seven years. My husband drank early on, but by the time we got a divorce after 10 years of marriage he was an alcoholic and would not seek help. We had a child and he has never been involved in her life. My third marriage was short (1 year) and I take full responsiblity for it's demise. I went out on my third husband and I still live with the guilt! I cheated on my third husband with the person that would become my fourth husband. My fourth husband came from old money and his mother ruled over him. this was a problem for our marriage, not to mention the guilt