A/C system not blowing cold air?

The car is not blowing cold air. It blows fine pressure wise and heats fine. Since November it’s only blown cold air about 5 to 6 times. I’m not a car guy but I’m pretty sure when it isn’t blowing cold the compressor isn’t on and when it is the compressor is on.

Out of the handful of times it has turned on it’s been after about an hour or so of driving. Mostly city with a little highway but when it does start blowing cold it’s out of nowhere and a mix of circumstances (once while parked for a bit and once while driving about 25 mph). If it does come on it stays on the rest of the time the car is on and even will continue to blow cold if the engine is turned off for 45 minutes to an hour and turned back on. The next day it will be warm air again.

Mech inclined buddy had me get a basic gauge and Freon (correct type for my car) to see if it was maybe low. When we hooked up the gauge it said over pressure so it doesn’t appear to be a leak or low Freon.