1. When he's asleep, dress up into a kraken costume and stand beside his bed. Poke him to wake him up and see what he does.

2. Leave a bar of soap on his desk. Add a note that says, "This is soap. I know you've never seen it before, and it might be kind of scary, but remember: YOU NEED A SHOWER."

3. Teach the crew "Hit Me Baby One More Time!" and get it stuck in their heads. Encourage everyone to sing it. All the time.

4. Buy a very realistic-looking fake tentacle and put it on Jack's neck when he's asleep. Poke him to wake him up and run away!!!!

5. If he keeps a journal, steal it and read the good parts to the rest of the crew for story time.

6. Buy a remote-control car and steal Jack's hat. Put the hat on the car and laugh like a maniac when Jack chases after it.

7. Tell him to stop using your mascara.

8. Sneak up behind him and scream "IT'S THE FLYING DUCHMEN!"

9. Set him up on a blind date.

10: ...With Will.

11. Fill his room with hamsters.

12. Whenever he tries to say, 'I'm Captain Jack Sparrow', walk up behind him and scream "We get it you overstuffed Spanish peacock!" (Highlander reference.)

13. Bake him muffins. Make him eat one. Tell him that they were from Will, expressing his undying love for him.

14. Ask him why he used the hair on his back instead of the hair on his head to rope sea turtles.

15. After you do all of this, pull him over to the edge of the ship. Randomly kiss him and then push him off of the edge of the ship. Shout "whelp overboard!" and point to him in the water.

16. Repeat.

17. Throw a dictionary at him every time he says savvy. When he asks why you did that, reply, "I need you to look up the definition of the word 'savvy.' I'm not sure it's real."

18. Steal his food and his rum. Refuse to give it back until he asks to marry you. When he asks (he will ask. You have his rum) say no anyway.

19. 'Accidentally' set fire to his hat. do this while the hat is still on his head.

20. Carve 'I love Will Turner and that's okay!" all over his cabin walls and his bed. Look at him sympathetically and say, "You do know that there is therapy for this kind of thing… right?"