During this season, called tsuyu, one comes to understand the fleeting nature of umbrellas in Tokyo. An umbrella can be gotten for as little as 100 yen -- I've never seen an umbrella for sale in the States for under $5.00, let alone under $1.00 -- and rightly so, because the chances of you holding on to that umbrella indefinitely are compromised at every turn. Either you end up leaving it on a train, or it gets wrecked by a strong gust of wind, or somebody just swipes it when you're not looking. All three have happened to me at least once.
You won't likely find people in Tokyo saying, "I wish the rainy season was over," however, because after the rainy season comes the worst summer in the four main islands of Japan. The tall buildings in Shinagawa and Mita that block the wind, the concrete coating the city and the hot exhaust of a zillion air conditioners combine to make Tokyo's summer reach temperatures even hotter than the southernmost island of Kyushu.
Hold on, I just remembered...as a Wisconsin native, it is decidedly bad form for me to complain about the weather in Tokyo. At least here I don't have to worry about my face falling off from frostbite.