A couple buddies of mine bought sport bikes. We had chatted before and they knew I could ride but was a noob, so one guy offers his tricked out Vulcan with forward controls for a day trip.
Needless to say, I started grinding hard parts in a shallow corner, target fixated a little on the shoulder, watched the front go off the pavement but then come back on. At this point I thought I was OK, then the back tire went off the pavement and kept going, in the most gentle and prettiest low side you have ever seen. Took the end off the clutch lever, ground the crap out of the left peg and some of the forward control, ground one of the pipes and scuffed one shock. All in all maybe $1k in damage. We finished the ride and chatted a little, next day he came into work and said don't worry about it. Still buddies to this day, frequently swapping bikes, I'm just jealous he turned a faster time at the drag strip on my bike than I did.
Dropped a coworkers dirt bike in a New Mexico desert at about 5 mph. You couldn't tell the scuffs I put on it over the ones that were already there. He laughed and then helped me wash off the 14" long gash in my left arm. He then proceeded to ride it while I watched and burned it down not 15 minutes later. I made up for the scuffs by helping push the bike the 3 miles back to his house.
I guess I'm the 'co-worker' and 'best friend' commonly referred to in this thread.