A very similar double-jeopardy bet on EVIL4.
WIN: 12 minutes sunning on a crowded beach (next summer) wearing a tiny speedo (nobody does that here)
LOSE: hosed down outdoors: swimsuit by day or naked at night - (next summer?) <freezing temperatures here>
LOSE: 6 laps around the outside of my house, naked, in the dark <might have to change due to freezing weather?>
My result (edit when puzzle completed):
Spoiler:
30:31 - Why am I so slow?