Here's one I pulled as a cop trying to be "Officer Friendly".
I had worked the midnight shift for three years in a row, and decided to go to the day shift. Having dealt with pretty much nothing but scumbags while working midnights, I was relieved to be able to see some normal people. I decided that I would drop in on some of the businesses in my zone, and do a little "PR" by introducing myself, etc...
I walked into a body shop and saw a nice looking woman behind the desk, and introduced myself as the officer that would be working this area. During the conversation I noticed one of those swimsuit calendars hanging on the wall, typical in a mechanic's shop. She told me to take a look at the picture for the month of July, and I discovered that she was the model for that month. As I continued to thumb through the calendar, I came across one of the models who was quite homely. I made it a point to show her the picture, and said "God, that woman has no business wearing a bikini". She then informed me in a very disgusted tone that this woman was her sister.
I soon figured out that whoever owned this shop had some of his aquaintances model for the calendar. Needless to say, I was quite embarrassed and left.