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The original was posted on /r/geocaching by /u/Twintig-twintig on 2025-05-22 12:17:33+00:00.

So I’m at this work conference today, all dressed up (heels, dress, makeup, the whole professional look). During lunch, I figured I’d sneak out for a quick geocaching break. I had spotted five caches just within a 2km round walk from the venue.

Well… what I didn’t do was check the terrain ratings. At all.

Cue me, twenty minutes later, halfway up a tree in high heels, balancing while trying not to rip my stockings (spoiler: I failed). Second cache was another climb. Third one required ”a tool” (very long stick), which I could only retrieve by wading through some small bushes. Fourth was finally an easy one and well, fifth I just gave up, my dress would not have survived another climb.

Now I’m back at the venue, picking leaves out of my hair, one stocking torn, and pretending I just “went for a walk to clear my head.” But hey, I got 4 out of 5 caches, and honestly, no regrets.

What’s your worst (or best?) unprepared geocaching adventure?