1. The Restricted Section of the Library
Things to consider: Filch, Mrs. Norris, those books that howl at you when you open them, your partner being a Voldemort-wannabe and only hooking up with you to figure out how to make horcruxes.
2. The Great Hall
Things to consider: House elves, unpredictable weather patterns of the enchanted ceiling.
3. Middle of the Quidditch Field
Things to consider: Madame Hooch, late-night quidditch practices, bludgers-gone-rogue.
4. Room of Requirement
Things to consider: Vanishing cabinets, Fiendfyre, Dumbledore's Army meetings, other couples with similar "requirements," Professor Umbridge and the Inquisitorial Squad.
5. Dumbledore's Office
Things to consider: Passwords, Fawkes, headmaster portrait peeping Toms and Dumbledore's stash of licorice snap.
6. Top of the Astronomy Tower
Things to consider: Cold drafts, fear of heights, Dark Marks.
7. Forbidden Forest
Things to consider: Unicorns, centaurs, Aragog, and anything you can find in "Fantastic Beasts and Where to Find Them," Hagrid taking Fang out for a midnight stroll, Hagrid taking Madame Maxime out for an afternoon delight.
Bonus points: The cupboard under the stairs. Make it to Privet Drive and win my affection. (Platonic affection, that is.)
Author's Note: Invisibility cloak strongly suggested.