These locks aren't made to lock before you close them. You must lock the driver's side from the inside only, then lock the passenger side with the key. And here's something I learned a couple years ago on here- back in the day, people were to exit the car/truck on the curbside for safety- that's why there's only a passenger side lock. I don't know if it was a law, but I was told it was common practice. On my dad's 49 Packard the passenger side door is a bit more wore out than the driver side, makes sense because the car had always been in the city. As for the key not unlocking the door, I'd say something is worn out in the door latch.
