Honey bees actually didn’t evolve to lose their stingers and die.
They can actually use it more than once in many of the animals that they have to attack, like in other insects. But mammals have thick skin, and their stingers just can’t help but get stuck in it.
The problem is that they have big strong barbed stingers, while most of the other bees have smooth and small stingers with tiny barbs. These barbs are what helps the bee to get the sting into the victim’s skin, but they end up making it more difficult for them to take the sting out of the skin is thick. So they end up leaving it and parts of its abdomen and digestive track behind.
Bee barbed sting: