Is it Really Random?

Every month, I make a playlist on my apple music. Sometimes playlists are pretty small, like 10~20 songs, but sometimes my playlist can be 60~100 (This is usually when I'm really into certain artist and download all of their songs to my playlist). 

When I listen to the playlists, I play the songs on "shuffle" mode. I've always been quite skeptical of this supposedly random order of the songs, because I would so frequently hear a few songs. I began to think if my music player started to learn songs I listen more (without skipping), because this "random sequence" seemed to favor music that I listen more than the others. But then I realized that I can never really know if something is random, or more meaningful than coincidence.