A friend was experiencing a really annoying problem with her iPhone. She would hit shuffle within a playlist or album. Instead of shuffling the songs on that list, it would repeat the first song over and over.
Took me a while to figure it out, but I found the problem and how to fix it.
While there are several web discussions about iPhone shuffle problems, I had trouble finding the answer but eventually did figure it out. This post should make it more obvious.
First, you need to tap the screen while you're playing a song. You should see something like this:
Notice the two orange symbols on the left and right just below the line showing how many minutes have played in the song. The one on the right indicates that it's shuffling songs. The one on the left is the important one for this post. If it's lit up like in this picture, it indicates that the same song will repeat.
Here's a closer look:
If you click on that icon on the left, it will change the repeat setting. Clicking it once should add the number 1, which indicates the song will repeat once. You're almost there:
Click it another time and it will go to gray, which means it's not repeating at all:
Now you should be done and it should work properly. Hope this works for you!