Imagine: you on your period and what the boys would do for you.

Dean: he'd pour some whiskey for the both of you. Then he'd cuddle you. Even though he didn't want to show it he was worried about you being 100% comfortable the whole time, making soft and gentle movements.

Sam: He would rent a whole bunch of your favorite movies and plan a marathon. Since he's a cuddly giant, you snuggled into his side all the while.

Gabriel: Would keep the water bottle warm with his angel mojo, and ibuprofen on hand. He is easy to make jokes about your monthly disturbance with out it being awkward. Really just making it awhole lot more bearable.

Castiel: he might not completely understand the right sentiments for this situation but he damn well tries. Flowers, chocolates, hugs. He makes up for his innocence in kindness.