Ive never had a large amount of money to blow , but I racked up 5-6 grand on credit cards in my 20's and 30's and to me that was HUGE.. It took along time to pay those off and I did default on a few, so my credit rating was effected in a big way.
I was so angry at myself but, I did have to forgive myself eventually.. You can only kick yourself in the butt for so long.