I too have ear pain within several minutes of putting an earring in my left ear lobe. This first occured about 20 years ago immediately after I had purchased a new pair of earrings. Within several minutes of wearing the new earrings, I developed acute left ear pain that radiated down my neck. My right ear tolerates earrings without any discomfort. The ear pain only occurs when I attempt to wear an earring in my left ear lobe. I have seen several physicians...but unfortunately none have offered a reasonable explanation or diagnosis. It was interested to read that others have experience ear pain related to earrings.
If it helps at all, about 18 months ago I got what I thought was an ear infection, took antibiotics and it went away. I woke one night to unbearable pain in my ear, I have never felt anything like it - I've had two kids and used to be a nurse, but I was crying like a baby!! The next day I saw my doctor who said there was nothing wrong with my ear, even though I couldn't bear for anyone to touch it, not even my ear lobe. Even my glasses resting on it hurt. I took my earring out because every time the back caught on something it made me cry. Eventually, it went away and I put the earring back in. A week later it was back and so on and so on and so on.... Being a bit stupid, it took a while for me to clock that every time the earring went back in, the pain came back. I haven't worn earrings since and so far so good. Not sure if it is related or not, but it could be.
I, too, have TMJ, and it does often manifest as ear pain. Wierd, I know, but it definitely happens. That also would explain why it comes and goes. I noticed mine came and went with my level of stress. The statement that you can't do anything for TMJ is wrong - you can't do much, but you can do some things. First, see your dentist. If anyone can help, it's her. Second, get a mouthguard. I know, not the most attractive or comfortable things, but they really, really do help. I was grinding my teeth and didn't know - one week with the mouthguard and I was golden. I know that TMJ is not the kind of pain that someone can live with - there are things you can do.
I hope this helps. If it doesn't, look into congestion in your ear canal, along your jaw line. That could explain the tenderness with your earlobe. Hope this helps!