I was saying: if there's a Caps game then after that, if none then whenever I feel like it. For digital stuff I have an iPod Classic that I use in bed with my Cmoy headphone amplifier (inside an Altoids tin!) with my Sennheiser HD600s. I do my best listening for some reason lying down, preferably in the dark.
When I'm listening to records then I have to sit in my (comfortable) computer chair by the turntable. (Long list of equipment follows which goes to the end of this paragraph.) Same Sennheisers, plugged into an Antique Sound Lab DT-OTL32 or whatever the #### it's called preamp-cum-headphone-amp with a Music Hall pa1.2 phono stage and a custom U-Turn Orbit turntable with a Grado Black body and 8MZ stylus; my DAC is a Monarchy Audio 18B.
I either turn the monitor off at my computer (no temptation) or have it up running Audacity and stuff if I'm doing any LP recording or ripping. Whether I listen to digital (in bed or on the couch) or analog (in the computer chair) depends on my mood and the longer trajectory of how I'm feeling.
Also I have a kind of insomnia where I wake up halfway through the night and can't get back to sleep for a couple of hours and I do some listening then. I think it's been going on so long that my body thinks it's natural order of things and *not* waking up early it would recognize as abnormal.
I fall asleep with my iPod plugged into a dick with speakers on shuffle.