I don't know about strangest, but it was definitely funny...I am a supervisor at my job and one of the things I regularly do is check approvals on large orders. So one day, this cashier calls me to her register and tells me she needs me to approve this check. It was only for $12 and change. I questioned her why I needed to approve this and she said to check the names. The name on the check and ID said Karen but her membership card (I work in a retail membership warehouse) was for a David. So I asked the "lady" if her husband was here with her. She said that she was David. I answered "No, you're Karen. It says it right here on your drivers license". As I said this I really got a good look at "Karen". She answered that she was David, but now is Karen. That she had had a sex change operation and that she hadn't gotten her membership card changed yet. I near died of embarrassment.