I usually find new memes tiresome, but I am really loving this one, as you might expect. It starts with the "James Van Der Beek Crying" picture, which is so old at this point that it practically creaks. But from there people have been using it to express 90s problems (particularly those which seem silly, trivial, or unbelievable to us today).
James Van Der Beek Crying
Although I must say that some of these are problems that I still face, to be honest. I don't have fancypants digital cable (I decided to use the money to get a streaming Netflix subscription instead). So I still have the problem of looking away from the TV Guide channel and having to wait until the channels scroll back around again.
But thankfully I no longer have to worry about things like CDs skipping, un-rewound VHS tapes, and phones with cords.