I think one of the dumbest dives I've ever done was a scintillating series of really BAD decisions on my part.
Based on my enthusiasm for his training, I proposed an overly ambitious dive to a visiting diver. The dive involved descending the shot line to a wreck and touring it briefly, and then setting out on a line to a second wreck lying about five minutes away. We agreed on minimum gas numbers before the dive. There were three of us diving, two in single tanks and one in large doubles. We descended and toured the first wreck, and reached the line and set off into the dark. Mistake #1: I didn't inquire of my unfamiliar buddy what his pressure at that point was.
We swam over to the other wreck, and just after we got there, my buddy signaled he'd hit rock bottom for the dive. I considered the situation: Surfacing at the second wreck was possible, but not optimal, as it would put us some distance from our boat and in a place where they would not expect to see us. There were three of us; I was well above my rock bottom, and the guy in doubles had tons of gas, so I decided that it was okay for my friend to go below his, as both of the other divers had other options, and it was better to go home. (I don't think this was a bad decision.) I signaled the third diver and told him we needed to go back, but I didn't tell him that our friend was at minimum gas, nor did I suggest that the two of them share some gas on the swim back to lessen the demands on my friend's tank -- Mistakes #2 and #3.
We got back to the upline and did our ascent. IIRC, my friend ended up with something under 500 psi (4, I think) when we got back to the boat. Nobody got hurt, and nobody got scared, but it just wasn't well planned or well executed. I learned a lot of lessons from that dive.