I've been going to garage sales and antique shops since before I was born so it takes a lot to stump me. This first item has me completely stumped as not only do I know nothing about it but I can't tell how old it is. 1930's? 50's? 80's? 2014?
The next item cost me $2 and it looks like it belongs with the Pyrex Drinkups.
Water got in between the plastic and glass when I washed it so they only way I could figure to properly clean/dry it was to unscrew the handle and take it apart. A little ridiculous if one had to do that everyday!