Off of the top of my head, I can think of a couple really embarrassing moments.
When I was still in the USAF, I entered a bike race as part of the base's sports day. I had done pretty well the year before, placing second in the women's division only behind the woman who had also placed first in all of the foot races. I think the only reason she beat me was because I was on a mountain bike and she was on a racing bike. The next year, she had transferred to another base, so I was confident that I would get first place. I didn't take into account the huge influx of new people to the base that also loved to bike, but that wasn't the real problem. The big problem was that I had left my bike out on my patio through the whole Texas winter and summer. As we left the finish line, my bike developed this very loud, very noticeable squeak, and people actually rode by, yelling "Squeaky bike! Squeaky bike!" at me.
This one is really bad. Still in the USAF, same base. I was sick with a head cold, I had eaten my lunch in this conference room at my office that also had a TV. I had fallen asleep in my chair for a few minutes watching People's Court or something, and when I woke up, there was a guy from the Comm Squadron working on the telephone lines in a closet about 10 feet away from me. I was worried that I had snored (a very likely possibility) while I was sleeping, so still half asleep, I said to him, "I hope I wasn't loud." He gave me this weird look and went back to what he was doing. As I grabbed my lunch trash and walked out, I realized that what I had actually said was "I hope I wasn't lousy."
Another time, when Austin and I were in Seattle, I walked three miles from the Space Needle to watch a Mariners game at Safeco field. With a giant rip in the ass of my khaki pants.
But nothing, nothing compares to the embarrassment of this, one of my senior pictures:
I am still not sure why I decided to pose with my semi-feral, gaseous, fleabitten tomcat. Let's not even discuss the Hard Rock Cafe pin, fake barn setting, or the Paddington Bear hat, artfully laid next to the cat. At least I didn't pick this one for submission to the yearbook.