Bad4shidduchim started the discussion regarding people making self deprecating remarks on a first or second date and how that can negatively impact the budding relationship between daters. Hannah at Ink Stained Hands took the discussion in a revealing newn direction based on a mishna in Pirkei Avos, which I find to be very interesting. She provides a new understanding of the mishna which not only makes a lot of sense, but isn't couched in misogynist terminology, as the mishna is more often interpreted. Both posts are worth a read.
I think we all, to one degree or another have a problem with this - unless someone is so full of themselves that they can't bear to say anything even hinting toward a personal flaw (and that is a whole different can of worms). I usually only realize I've said this sort of thing in hindsight, but I am pretty sure I avoid anything of this sort on the first date or two. I'll definitely be more aware of what I say in the future, and cultivating a conscious involvement in the dating process is always a good thing.