Thank you, Joanne Rowling, for reawakening the fun I used to have with shipping. Let's follow this current where it will, shall we?
Day 1: Your first ship ever!
I think it was Bernard/Bianca from Disney's The Rescuers. I started a story set after The Rescuers Down Under, called "The Rescuers Get Married," but I don't think I got beyond the first paragraph. Considering I was barely eight years old when TRDU came out on video (thanks IMDB!), I think it's safe to say that was my first ever - however brief, feeble and ill-fated - attempt at fan fiction, and probably my first dip into what you would consider "shipping." I think I remember finding Bernard's crush on and devotion to Bianca sweet; I vaguely recall being irritated every time the Jake character in TRDU kept interrupting Bernard's attempts to propose to her and relieved when he FINALLY got to do it. Looking back on it, I still think fondly of the movies, especially TRDU, but I now see Bianca as almost totally useless, and frankly kind of ditzy. I suppose she wasn't so totally passive as so many Disney heroines up to that point - she was willing to get her hands (paws?) dirty - but for a titular "Rescuer," she sure ended up needing a lot of rescuing.
Day 2: A ship you've just discovered
Day 3: Your OTP
Day 4: Favorite crack pairing
Day 5: A crossover pairing you think would work
Day 6: Series that you have many ships in
Day 7: A pairing that disappointed you
Day 8: A pairing only you seem to like
Day 9: Your least favorite couple
Day 10: Ship that became canon even though you didn't expect it to
Day 11: Character you like with several others
Day 12: Character you don’t like seeing paired with anyone else
Day 13: Couple you ship that causes intense feelings in its fandom (read: flamewars and the like)
Day 14: Couple you liked even though you knew it would end up badly
Day 15: A ship canon really messed with
Day 16: Favorite villain pairing
Day 17: Ship you talk(ed) about with people in real life
Day 18: Most annoying character that tried to come between a ship
Day 19: Favorite Hero/Villain pairing
Day 20: Favorite couple played for laughs
Day 21: Favorite opposites attract couple
Day 22: Saddest unrequited love
Day 23: Couple you only shipped after a long time
Day 24: Couple you like, but is overshadowed by another couple in a fandom
Day 25: Most popular couple in your favorite fandom (do you ship it too?)
Day 26: Best historical couple
Day 27: Another couple you shipped a long time ago
Day 28: A couple you shipped not nearly as long as you thought you would
Day 29: Favorite ‘birds of a feather flock together’ couple
Day 30: Couple you will still ship a few years from now