Hm. I've had a lot of these though most of the extreme end of the awkward scale tend to be parent-related.
I had left the room for a while once while my(then) girlfriend and mom were talking, which was a big mistake on its own. When I came back in they had somehow gotten on the topic of whether I would look good with some sort of piercing and/or tattoo. Right when I came back in my pointed to the spot between her lip and chin and stated that I would probably look good with a 'taint brush' and they both turned and looked at me to get my opinion.
I had left the room for a while once while my(then) girlfriend and mom were talking, which was a big mistake on its own. When I came back in they had somehow gotten on the topic of whether I would look good with some sort of piercing and/or tattoo. Right when I came back in my pointed to the spot between her lip and chin and stated that I would probably look good with a 'taint brush' and they both turned and looked at me to get my opinion.