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Voltorb. Hopefully it'll roll away far enough before it blows up...Cacnea I'd probably get spikes lodged in my food and then I'd have an angry cactus chasing me.
Face a horde of angry Ursaring in a forest or be trapped in a cave with a single Bewear?
Sit on a Ferroseed. I might be able to position myself so that I don't sit on spikes...I see no way how I can avoid melting myself if I hug sentient molten lava. xD
Become one of Spiritomb's 108 spirits or be trapped inside a Cofagrigus?
Definitely the former. Not only do I find Spiritomb a lot less creepy than Cofagrigus, but it would also feel more reassuring with 107 other spirits to share my pain with. xD
Have Youngster Joey call your phone number every two seconds, or have Professor Oak's voice tell you "this isn't the time for that" every single time you attempt to do something?
The latter...I sometimes get that in my head anyway.
Spend a night "alone" in the Old Chateau, or spend a night "alone" in the Pokemon Tower? Both complete with haunting background music playing from somewhere you're never quite able to locate, of course.