So funny that this topic came up. On a couple of recent group rides, there's been a guy wearing the same pair of threadbare shorts. It didn't help that it was an old team kit that had a gray panel strategically positioned. I was behind him on one of the rides and I got quite a view, even more so once he started sweating and gray became somewhat see-through anyways. I didn't know him and didn't know how to tell a total stranger that he really needed a new pair of shorts. I asked one of the other guys after the ride. He told me to be blunt -- hey, dude, get some new shorts, we really don't want to watch your butt-crack the whole ride. I didn't get a chance to say it, not sure I would have the guts to be that blunt. I did notice that he had a different pair of shorts on a couple of days ago so he either hasn't done laundry or someone else broke the news to him.