This thread is still the first result in Google for "headphone group delay" so I think it's still significant to have an actual ELI5 answer. This thread is hilarious to stumble across. Once you understand group delay, it's funny to go back through the thread and see where people are technically correct, and where they add obviously unnecessary detail. Some of the below is copied from the
YouTube video already mentioned in this thread, but I couldn't find anyone posting an ELI5 explanation as easy to understand as the video.
Group delay refers to different frequencies being delayed different amounts.
If you send an audio signal through a device, and the bass frequencies are played with 1ms of delay and the high frequencies are played with a 2ms delay, that's an example of group delay. Each "group" of frequencies is "delayed" a certain amount. When different frequencies in the same signal have different delays, that's group delay.
If you send an audio signal through a device, like a wire, and you get the same signal out the other side, there is no group delay in that device. If some frequencies come out the other side at the different times, that's group delay.
The critical thing is to tie this back to headphones. Everyone keeps coming to this thread to understand headphone measurements. Headphone group delay doesn't really make sense on the surface: You're saying that a headphone driver, a few centimeters away from your ear, is producing an audio signal where the frequencies coming out of the driver have variable frequency timings, different from the signal going into the driver? That the driver itself is making a waveform where the bass notes hit your eardrum milliseconds sooner than the high notes? No!
Amir's post is a little dense and terse, but makes sense now that we know what group delay is. He's saying that audio bouncing around inside the cups getting
combined with the original signal can make it sound like that part of the signal is delayed. In a device like an amplifier, group delay might be from electrical signal processing. In a headphone, Amir is measuring the audio reflections in the cups combining with the original signal, not from the driver itself. At least, I haven't seen any of the reviews cite the driver as the reason for group delay, it's always reflections.
Group delay might* affect the soundstage/imaging of headphones. Your ears determine where things are in the world by the phase at which signals hit each ear. Your ears are very sensitive to this. If different frequencies in a signal have different delays, it affects your ability to perceive/imagine where the sounds sources are in space. I haven't seen any data on what level of group delay has a perceivable effect on soundstage (and soundstage may be impossible to objectively measure anyway).
* the group delay measured on ASR is the same for both cups of a headphone. If the group delay is the same for both ears, does it actually affect soundstage? Now that's
a good question!
Once you understand this, it's a lot easier to see where other posters start to explain it and then get lost in the details of digital signal processing, because they're trying to be more accurate with their details of the explanation. I find it entertaining and fascinating that the more technical details people add, the more muddied their explanations become.