Fantastic topic, so many good laughs. The penguin is just hilarious, or the story with the friend's car
I've experienced similar things, for example
Talking loudly to my self (in German, luckily) on Sgurr Choinnich Mòr (Grey Corries) about how bad that ridge down Stob Coire Easain was and that "No thanks, this time I will not try to bypass anything but walk stright up the ridge, do you understand, mountain?!", only to turn around and see a guy approaching with a big question mark in his face...
On my way to Mont Buet, forgetting my SLR on top of "Le Cheval Blanc" - French Alps, sitting right on the border to Switzerland, 2831 m (yes, not feet), many kilometres from civilization. Luckily the only guy I met all day long was on the summit at the same time and came running after me with my SLR when he spotted it...
French Alps again, drove one and a half hour from where I lived at the time to Chamonix to go up Le Brévent (2525 m). Arriving at the parking, opening the trunk, and not seeing my walking boots... In retrospect, I'd have loved to see my face... I did the circuit with the trainers I wore to drive. At the end of the day, after walking over all the Karst, they were ready to be thrown away...
Finally, the memorable day out in the Lake District with Mrs. Zatapathique. We walked from Borrowdale via Glaramara to Allen Crags, then back through the Grains valley. After some lunch in the shelter on Glaramara, the clouds moved in and we couldn't see far. Off we went, always straight south south west - or so we thought. After an hour, we finally spotted what we thought to be the summit of Allen Crags. I said "Hey, look - there's a shelter, too." - Mrs. Z.: "Yeah, looks exactly like the shelter on Glaramara" - Z.: "Wait a minute, it IS the shelter on Glaramara..." We had a good laugh before doing what we should have done in the first place - get the compass out of the backpack and navigate properly... Since then, we refer to this incident as the "Glaramara Roundabout".
Our path is wonderfully confusing, isn't it? Something went wrong half-way, but more seems to have gone wrong already in the beginning. We never had the impression of going round in circles, certainly not several times...
(You can see more details when you open my file in OpenTopoMap. I'm quite sure I'm not allowed to upload a screenshot of it here, otherwise I'd have done it.)