Quick story, but a very fun one. This was about 8 or 9 years ago when I was working at a bank in the sales department, and although I didn’t actually do any sales, I always got to be a part of all the sales conferences and events. There was a conference taking place in Hawaii and at the time I was dating one of the sales guys (Edgar) so it was going to be a free vacation for us. Of course the company booked each room as double occupancy and same gender only but we planned to pay out of pocket for a few more nights after the conference for ourselves.
As luck would have it, my bf got paired up with one a co-worker from my team, Phil; so I asked him if he would be okay with me staying in the room with them and he was fine with it! (I actually tried to get him to swap rooms with me, but the girl I was sharing with didn’t go for it).