On a floor with a stack of textbooks as pillows at a college frat house after way too much Natural Ice. This was New Year’s Eve 12/31/99. I still recall how awful I felt the next morning. Happy new millennium?
Though, I’d say the most awkward/worse night of sleep ever was after a date. Had driven two hours away (was set up). Date went fine, we were drinking, then unfortunately it turned political. Basically, she goes really sharp in one political direction (doesn’t matter which way as I can’t respect either extreme) and I said something half joking to push her button. Again, we are both drunk. Well, she storms off and I basically have to chase after her bc my car was at her place and I had never been to her town before. This is also pre-Uber and taxis weren’t readily available (Duluth Minnesota back in the mid-2000s).
She’s annoyed but eventually we get back to her place and she’s like “what are you doing??” I go, “look, I know this date needs to end but I am legitimately drunk and can’t drive. If there’s a hotel nearby I’ll happily walk to it but I don’t know what else to do. If I thought I could drive I promise you I would but I’m drunk and I really can't.”
It was cold, so to my somewhat fortunate surprise she tells me I can come in to sleep. She had a small apartment so no guest bed. With serious hesitation she tells me I can sleep in her bed but I can’t touch her. I slept in my clothes on top of the sheets. About six cold, very awkward hours later after some terrible sleep I feel sober enough to leave so I do. Never spoke to or heard from her again.
Tl;dr: Worst night of actual sleep was wasted NYE and slept on a floor and literally used textbooks for pillows. However, most uncomfortable was sleeping in the same bed with a girl I just met who absolutely hated me.