Do you ever find that you chronically put yourself back into a situation even knowing it will have the same disappointing result?

Yes, often. I know the definition of being mad is something like “repeating the same actions and expecting different results”.  If that’s the case, I’m only half mad then. Cos I know I’m going to end up same results.  But I can’t seem to stop myself  making the same stupid mistakes. Or maybe I don’t want to, I dunno. 

Well now I’m depressed lol.  

One thing that can be called is addiction.

The positives I guess tend to get glorified and the negatives repressed.  So part of us doesn't really know any better until we find ourselves back in the same situation wondering why we didn't remember how bad it makes us feel. I sometimes wish I could just say "enough" and actually mean it because I know the wavering back and forth only leaves people hurt. 

Yeah...waking up.

Isn't that 100% what dating is?

Yes - trying to talk politics on this site. 

Sometimes, sure.  But I guess that's partly what life is about .. learning to cope or laugh things off if that's what's needed. 
Doing things over and over again that are dangerous or unhealthy .. hopefully, we learn from our mistakes and don't do them repeatedly though.

I like to make an effort of learning from failures. What you describe is the effective definition of insanity. I avoid such practice when I have power to do so. 

No.  I'm smart. 

Darling, that is the definition of music lessons!