I agree with everyone that you should trust your gut about creepy situations. I also probably tend to be a bit over-reactive about perceiving creepiness in strange men though...
I do have a question about this "riding behind a stranger" issue though --
I was riding the other day with a girl from one of my classes. She was struggling along on a mountain bike with underinflated tires... working really hard. After accidentally losing her a few times, I suggested she ride ahead and I would follow (since I certainly wouldn't want to always feel like I needed to catch up). This went well and we continued for most of our loop this way, until the last section which is a gradual, but very long hill. She was really struggling and told me to go ahead and she would catch up. I didn't really feel good about doing this, but she insisted. So I went ahead, then at a certain point slowed down quite a bit, to look behind me (I didn't want to get too far ahead). As a was coasting uphill looking behind me, some guy in full kit from somewhere, full skinsuit, booties, matching windbreaker, etc, fancy bike, rear mounted bottle cages, passes me. This piques my competitive devil a little bit (dude, don't think you're that much faster than I am just because I'm a girl on a pink bike coasting uphill) and I catch him and stay with him for about a mile. We were going fast -- a pace I could sustain but one which had me working. It was fun... I was not right on his wheel, I would say half/three quarters of a bike length behind. At that point I pulled into a driveway to wait for my friend (we were riding on a somewhat busy road that is popular with cyclists for its rolling hills, wide shoulders and gorgeous views). I didn't announce my presence or try to talk to him, it's possible that he didn't even know I was there, since I never saw him look back (though I could hear him shift so presumably he could hear me shift as well).
At the time I was unsure if it was "rude" to follow a stranger like this -- would my behaviour here fall into the same creepy/annoying category as this white-bearded guy???



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