The last overnight of mine that I had a 'date' for was the summer of 2001. It was like the good old days, we had 23 hours in DCA, and we stayed at this beautiful hotel a few blocks from the White House. We went to the Air & Space Museum and walked along the mall, it was amazing. Loads were great, and he got to sit in First both ways. I actually held a great line with those same overnights the month of Sep 2001. Too bad I never got to fly any of those trips.
The last overnight I went with my husband anywhere was New Year's Eve last year. I met up with him in BOS, and I got there early enough to go with him on his PBI turn that he had to do before we went to the hotel. He had a pretty short night in BOS, we got in at 2230, and all he had to do the next day was deadhead back to CVG. Thankfully I still had my pass card from American, so we took AA direct back to ORD and came home early in the morning. (Loads were too heavy later in the day.) Even though it was a short night, it was New Year's Eve, and I didn't want to be alone! Besides, New Years is actually one of the easier holidays to non-rev on.