I find that this works very well on some women, and is personally one of my favorite styles of humor because I genuinely find making fun of myself to be funny. Recently though there were two instances where I tried to use it and it misfired. I don't remember the actual joke but something all the lines of "yeah back when I was young and stupid.....now im just old and stupid." The woman I was speaking to, instead of laughing goes "awwwww dont talk about yourself like that youre not stupid." Full of sympathy. I kind of just looked at her dumbfounded and said "....it was a joke." I used to land these jokes all the time, but its been twice now that I've gotten that reaction.

Anyone else use have good or bad experiences with this type of humor?