What's the dumbest thing you've ever said?

What’s something that you have said in the past that you immediately regretted and wanted to take back?

For example… my friend’s mother died recently after a long battle with cancer. I suppose I was just in the habit of asking this person about his mother, but anyway… I waltzed right up to him and asked “So how’s your mother doing?”

Yeah… it was awkward and I just about vomited with regret =/