Once in a PA-28. I was doing practice approaches. I planned to switch tanks at the IAF. Reaching the IAF, I heard a friend on the radio and my thought was “I need to return the wrench that I borrowed” instead of switching tanks. It sputtered after turning inbound on the approach. I was kind of getting into test pilot mode with my RV-14 at the time, so I reacted quickly and accurately (pump, mixture, change tank) faster than I truly realized the tank was empty. It came right back to life. I bet I would be a lot slower now that I’m a little rusty on all the emergencies I had been chair flying in my half-built airplane every day.
Several times in a C310. The fuel selectors on each side are main, aux, crossfeed, and off. The crossfeed is from the other main tank. So if you lose an engine, any remaining aux fuel on that side of the plane is unusable. Many folks run the aux tanks as near to dry as they can to minimize the unusable fuel they carry into an engine failure emergency. Sometimes, that leads to a noisily sputtering engine and yawing airplane. Sleeping passengers do not enjoy this one bit.
Nobody is perfect. Your friend doesn’t have to hang up his spurs just yet. He should at least try to keep flying until the pickleball craze dies down a bit and the options outside aviation improve, or at least get better names.