Oh, I hate those anxious thoughts in the middle of the night! I worry about my husband dying and getting old and being alone, etc.

My sleep cycle is horrible too but I'm retired so can sleep in every morning or go back to bed (like I did today). I was dreaming of being in the woods in the fog when I was napping this morning/early afternoon :-) It was a little lonely/quiet and spooky.

I would think you were dreaming about teeth because you were focusing on cleaning them :-) Teeth dreams are common and often have to do with looks and you did say a couple times you're worried about looking old, etc.

I vary the different things I take to get to sleep; one night I'll take nothing, one night I'll take a Zyrtec, one night a Benadryl and another an Advil PM, etc. I mostly don't take anything (since I don't have to get to work or anywhere the next day) and I, too, am trying to get my sleep hygiene more consistent so I go to sleep similar times each night and get up same time, etc.

You might have your thyroid and other hormones checked? Guys have problems with thyroid too and that can mess with one's sleep (what most of my problem is).