For very few friends will I break out the crazy. The Bestest Friend is lucky that I love her as much as I do.

The Bestest Friend has been dating the same guy for the past nine months; they’ve been having on-again-off-again trouble for the past five. This past weekend, she asked for my help, and in accordance with The Bestest Friend Obligation Handbook, I helped with her stalking mission. The process is more complicated than I first assumed.

Steps for becoming a spy:

1. Learn passwords (both email and voicemail).
2. Check email.
3. Discover an email confirmation for [hotel booking website] for upcoming weekend.
4. Check voicemail.
5. When message plays from Questionable Skank, write down phone number; have Excessively Crazy Friend (note: this was not my role) call repeatedly and then hang up.
6. Have a male voice call hotel, requesting that a key be left at the front desk for [Bestest Friend] who will have the [hotel booking website] printout as confirmation.
7. Around midnight, pick up hotel key and enter room.
8. Upon discovery of the baggage for one male and one female, unpack bags to determine contents. Note the pants-size of the female as well as the inclusion of complete make-up set and phone charger.
9. Steal bags.
10. Chain smoke on hotel patio.
11. Do drive-bys of favorite bars, looking for familiar cars in parking lots.
12. Return to the hotel for more chain smoking on patio.
13. When cold, decide to wait in the room.
14. When still cold, what the hell, wait in the bed.
15. Debate ordering room service. And leave it untouched.
16. Do not accidentally fall asleep.
17. When male and female suspects enter room at 5am, make introductions.
18. Do not leave partner alone in room with Questionable Skank. Especially if leaving permanently.
19. Answer phone calls and/or texts from partner trying to escape awkwardness.

The worst part is that he talked his way out of it. He was only dropping her off! The hotel room was for a friend! She was supposed to go home with her three friends from the party! The Bestest Friend has forgiven him and they are taking a long weekend together. They even laugh about it now, with him saying how he can see how it could be misinterpreted. And, according to The Bestest Friend Obligation Handbook, I have one opportunity to express my doubts/concerns and then let her live her life. Because that is exactly what I would want her to do for me, what I expected her to do for me if I had gotten back together with The Kid. But I still worry that in ten years, she will still be the girl in his hotel room, waiting for him to walk in with another woman.