I had one of these silly connectors, it was very fickle - solved it by pushing a screwdriver through it and breaking off the silly little internal valve - worked fine after that
You could have just swapped the hose round so the pressure from the tap served to push the valve open, rather than closed
Oh because everyone else is saying aquastop goes on Pressure washer side and the one without aquastop goes on tap
Normally, yes. That's because normally you want it to be the case that water shuts off when you disconnect the hose
The problem you can run into though, especially with pressure washers and other things that don't let water flow freely, is that there can be water already inside the machine, under pressure, plus water in the hose under pressure, and you have to be strong enough to overcome the water pressure when pushing the connector on. It's easy to underestimate just how hard you have to fight against mains water pressure; it's significantly to easier to turn the power off to the pressure washer, then pull the trigger to relieve all internal pressure inside the machine, and keep the trigger held while you plug the hose in. This way the water pressure in the hose has somewhere to go and you don't have to fight it so hard
Other things to consider with pressure washers; sometimes the thing you clip the hosepipe onto has a built in filter that can get clogged, starving the washer of water. If you don't have a filter it's also possible to get a bit of grit into the washer and down the lance, blocking the outlet from the nozzle. Better washers come with a small tool (a slim metal wire to poke with) to clear the nozzle.
If the machine is under pressure, release the pressure with the power off, then disconnect the nozzle end from the handle end (if it does) and manually. After this you should be able to poke it clear. Before running it again backwash the nozzle with the hosepipe so the same bit of grit doesn't immediately make its way back into the outlet jet