CIRCA
Pun Play: You can only SPAN so much time with a loser.

My Gameplay: ADIEU, PAINS, CORKY, CIRCA
I’m pretty sure I wouldn’t have been able to solve this if I hadn’t randomly tried tried CORKY when I couldn’t think of anything else. It was a heck of a guess too as it gave me two letters in their proper spots. You can’t ask for more than that when you’re feeling down and out. TGIF everyone — you made it. On to tomorrow!