On occasion I have been known to stick my foot in my mouth, so to speak, as has been demonstrated in several blog posts. Here's one more ...
In my late teens I went on a few dates with a girl named Kim. Since I was away at college most of the year it didn't progress much further than that. After that she started dating another gentleman, and she later got pregnant. I had heard that they were thinking about getting married, but not until after the baby was born.
Fast forward to the next summer. My incredibly handsome twin brother Ron and I were walking in the mall (kids, ask your parents), and we saw Kim. Here's how part of the conversation went:
Me: When did you have the baby?
Kim: I had a miscarriage.
Me: Oh, I'm so sorry. Did you and your boyfriend get married?
Kim: No, he dumped me right after.
Me: Are there any other questions I can ask to pour salt in your wounds?
After we walked away my brother said, "Well, that went well. At least you didn't ask her out."
I replied, "Yeah, I thought I would wait a couple of weeks for that."