I've got a funny story on this one: last summer at our local public pool I had a rather chatty lady sitting on the chair next to me; she wanted to "know her neighbors" she said. She had two children with her that appeared to be somewhere in the 8-11 range. I'm not sure how old she was, but if I had to guess, I'd say somewhere around early-mid 30's.
So, I'm sitting there wrangling DD2 into her lifejacket, and chatty lady tells me that my granddaughter is really cute. "Um, no, actually this is my daughter." So she says, "I'm sorry, I really thought you looked old enough to have grandchildren -- I mean ... old enough to have a kid who had a baby as a teen." My reply was, "Well, I hope not to have any grandchildren for quite a long while; seeing as how my oldest is only 12."

She sputtered a bit, and then tried to dig her way out with, "Well, anyway, your husband is really good-looking!"
Every time she tried to fix one unfortunate comment she just stuck that foot a little deeper into her mouth.
Of course, at the time I was exactly ... 47.
