Once while commuting to work I was taking the long way so I could descend a nice curvy road. This road has two nice curves in succession and on the first I carved it like a pro (in my head) so flush with pride I thought I would really carve the next one and so of course I went over too steeply, my wheels went out from under me and I literally slid all the way across the road - from one side to the other. I was very lucky that A) the curb was very high which stopped my progress which would have otherwise carried me over an embankment and B) that no cars were coming at that time (shudder). Adrenaline took over and I completed my ride to work but my very bruised flank stiffened up over the day and I rode the bus home equal parts shamed by my crash and relieved it wasn't worse.
On a weekend ride part of my route took me on a bike path that skirts a fairly industrial area and at one point the path takes an S curve that is bisected by railroad tracks. I was going pretty slow, probably 5 mph, but I was thinking about the curve rather than hitting the tracks with my wheels perpendicular so of course I went down as my front wheel went out. This crash was memorable for a couple reasons. First of all even though was going slow my wheel went out so fast that I was levered to the ground quickly - head first - and I saw stars like I was in a looney tunes cartoon, I shudder to think what that would have felt like without my helmet on, not meaning to preach here just sharing an experience. Secondly the crash popped my tire and I used my only spare repairing the flat so, shaken up and with no spare tubes, I cut my ride short and turned around and headed home. On the way back I had to climb a hill and I had just lost a bunch of weight and I was amazed at how easy climbing that hill felt now that I wasn't lugging the equivalent of a 2nd grader along with me.
When I started to ride a road bike to train for the Seattle to Portland ride back in 2000 I got introduced to riding clip-less pedals....yeah there is a learning curve. Early on my issue was that I would most often clip out on my right for a stop and sometimes end up leaning left - where my foot was still clipped. Yep slow motion topple with my clipped out foot failing uselessly, I'm sure it looked pretty comical. And in the "I can laugh now category" my first clip-less shoes were Specialized Mt, bike shoes that had both laces and Velcro closures, on a training ride I happened to glance down and notice that a shoelace loop was coming out from under the Velcro closure and as I was thinking "this is bad the lace is going to get caught in my chain" that is exactly what happened and boom I am on the ground with one foot clipped in and and trapped under me and the bike and the other clipped in with a lace tangled in my chain and to make it even better I am halfway in the road! So I shimmed my way on to the shoulder -I am sure I was the picture of grace -and somehow freed my foot from shoe and managed to extricate myself. Not my finest moment on a bike.
And my final embarrassing story involves a turtle. I was out on a fine spring day with the sun out for a ride around the neighborhood. I was descending a moderate hill intending to take a left hand turn and continue down to the waterfront. I was in luck as the turn lane had cleared and the light was green and I had a good head of steam off the hill and then it all went pear shaped, the next thing I knew I heard a loud yell (it was me) and I was literally sliding on my stomach toward the cross walk. I later realized later that I had gone too far to the right of the turn lane to set up my turn and my front wheel had clipped a traffic "turtle" that is used to mark the lane and hitting the little raised half circle had precipitated my crash. Two things stay with me about that crash, 1) there was a bus stop at that corner and a bunch of folks came out into the street to help me up, collect my bike and gear and see if I was ok - they thought a car had clipped me -it was one of the coolest instances of spontaneous kindness towards a stranger I have had the honor to witness and 2) my synthetic "Old guys who get fat in winter" jersey was unscathed despite being skidded on the pavement - I expected it be in tatters - must've been weaved with Kevlar.
Oddly since I have stopped worrying about speed on the bike and concerned myself with enjoying the journey my crash rate has dropped quite a bit...hmmm.
As always Ride (safely). Smile. Repeat