People will find it weird but I listen to music in monthly playlists. I have a playlist for each month (filled with songs that I've been listening to in the respective month throughout the years), and I only listen to the current month's playlist.
I associate songs with time of the year/seasons/memories and it feels very appropriate doing it like that lol (and it does make you miss the songs and love them even more each year). Yeah, it's that terrible
