I've considered trying a singlet several times now because of summer heat, but just haven't gotten around to it yet myself.
As for the grass, I find it pretty fun to run on grass when it is not a race, because it is softer and not as rough on the body to run on.. but when racing, I definitely go slower in grass. It is tougher to keep an efficient motion due to the surface being softer. I'm not sure that I would enjoy trying a 5k race with a finish in grass myself.
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Couch to ??k - From the couch to a Marathon in roughly 18 months.
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