original meme put together by gypseian and found via levstrong; I just made edits to it that worked better for me. The only rules I can see being important are, “have fun,” “don’t be a dick,” and, “no, really. I mean it. Don’t be a dick.”

Day 1: Which is your favorite — Claire, Jesse, Ben, or someone else — and why.
Day 2: So, the main fanon casting for Team Free Will 2.0 is Claire, Ben, and Jesse — do you have a different casting for yours? If yes, who’s in it? If no, why not and who else would you consider including, aside from Claire, Ben, and Jesse?
Day 3: Who is your favorite supporting character and why?
Day 4: Who is in your dream cast?
Day 5: Favorite slash pairing and why (dudeslash or femslash).
Day 6: Favorite slash pairing and why (whatever the opposite of day 5 is for you). Alternately, your second favorite pairing of whatever kind of slash you did for day 5, and why.
Day 7: Favorite het pairing and why.
Day 8: Favorite non-romantic relationship and why.
Day 9: What’s your head canon for Ben?
Day 10: What’s your head canon for Jesse?
Day 11: What’s your head canon for Claire?
Day 12: Is there any “Supernatural kid” that you feel should get more attention in the TFW2 fandom?
Day 13: Is Ben Dean’s son? Why or why not?
Day 14: Claire somehow tracks down Castiel. How does she react?
Day 15: If you have a least favorite character, why? Alternatively, what is your favorite snack to take on a road-trip?
Day 16: Describe TFW 2.0 in 5 words or less. Alternatively, write a 5-sentence fic about TFW 2.0.
Day 17: What’s your head canon for a non-Ben, Jesse, or Claire potential member of Team Free Will 2.0?
Day 18: What brings Team Free Will 2.0 together, in your head canon?
Day 19: How do you feel the members of Team Free Will 2.0 correlate to the members of Team Free Will?
Day 20: Where do you think the Winchesters are?
Day 21: If you were in the SPN!TFW2-verse, what would you be? A hunter, a researcher-informant, a sidekick, an angel/demon, or a baddie? Something else entirely?
Day 22: Favorite fanfic and/or fanart.
Day 23: Suggest a tumblog to follow that is TFW 2.0 friendly.
Day 24: What do you want to see more of in fan discussions about TFW 2.0?
Days 25 — 31: In the spirit of fee will, the last seven days are all free choice. So, make a and/or write a ficlet/poem/haiku/whatever floats your boat, and/or write some meta, and/or make a graphic. Do whatever makes you happy.