I had one aggressively geared SS that had me hanging my head on steep uphills. Those walks were shameful. Now I'm geared; can't deal with spinning out on downhills that immediately precede taller climbs.

Mechanical walk of shame- got a flat 4 miles from home with no phone or convenient public transit solution, and could not re-mount a 25 gatorskin to a bontrager fairlane rim. I considered using the tire levers but i have ruined tires/tubes in the past using tools to get that last little bit over the edge.

I bought a plastic tire jack because of that incident; the one the dude at the LBS had to use on that tire/rim combo, as he could not do it with his hands either.

The upside to that flat: About a mile into the long walk back, a cyclist pulls over and asks if I need assistance. I explain the problem and that I'm fine with walking, and whaddyaknow the guy is trying to recruit me for his church. Even though I made it clear as soon as I knew what was happening that I wasn't going to be visiting his church, he walked the other 3 miles with me, being neither overbearing or unwelcome. I felt no pressure from him, and we had open and unoffensive dialogue that explored different interpretations of religion, science, and the earth on which all the tangible exists but most importantly passed the time.

It was all in all a pleasant experience.