When I moved from the midwest to Seattle in the summer of '99, I figured I could just drive until I got exhausted and then grab a motel room for the night.
What I didn't count on was A) I-90 is empty as shit across South Dakota/Wyoming/Eastern Montana and B) that I had decided to make this drive during the Sturgis Rally. So, first night of travel, somewhere in BFSD I discovered (at 11:30 PM) that there weren't many hotels/motels and the ones that did exist were booked solid for hundreds of miles. I kept driving.
About 2 AM (4 AM, since my brain was on Eastern Time), I decided to try one more place. Pulled up, walked in, and the "proprietor" said- "He just got the last room" as he was pointing to a dude just completing the paperwork.
Dude looks up at me and says- "You look like hell... I'll split the room with you". Looked at the innkeeper, who shrugged and said "two queen beds". So, in a combination of youthful arrogance and exhaustion enhanced stupidity, I agreed.
Was an uneventful experience (dude ended up being an ordained minister who worked for a national non-profit... we actually knew some of the same people), but certainly falls in the category of "What in the hell was I thinking?"
Slept in the backseat of my car (was pulling it behind the moving truck) the next night somewhere in the mountains between Missoula and Spokane.