Taunt The Evil Millionairess With Letters Falsely Declaring Your Undying Love Day!
She had the orphanage evicted. And she had the mayor drive out the animal shelter because it upset her allergies when she'd drive past it on her way to her jewelers. Plus, she's commisioned a death ray.
It's time someone made that old bitch cry!
Turn up the heat high enough and even the iciest of hearts are gonna melt. You can get through to her. Just pace yourself. Be mysterious with the first few letters, saying you two have been on a first name basis for years, but you won't reveal your identity to her for fear of her denying you her presence. "I would rather carry my love to my coffin than risk never seeing your beautiful face again." Write that. Did you write it?
Her first letter back to you will be cautious, but she will make sure her words carry just enough warmth to encourage you to write again. This woman may be evil but she, like everyone else in this miserable town, wants to feel loved just once more before she dies. Make her think her wish is about to come true.
As I said, her first letters will be cautious. "I appreciate your kind words but I am far too old and far too busy for such silliness." She'll write that. You should respond with, "I understand, and since I respect your well-being above all else in this world, I won't write again for fear of irritating you in the slightest." Be sure to drop some hint as to who you claim to be or where your life has taken you. Like this: "A brutal winter thus far. I haven't felt such a chill since my years in Stockholm."
That'll give her an in to write back with something like, "Stockholm? What a coincidence. I've been led to believe that my sister settled there after Father cut her off for marrying low. Perhaps you know her?" Don't worry about it being a trap. She hasn't spoken to her sister in 25 years and the only reason she believes her to still be alive is because the family's lawyers always let everyone know when one of them has died. Just say you traveled in a very small social circle when you were there and so it's unlikely the two of you would've met.
At this point the bag will do whatever she must in order to keep your correspondence alive. This includes agreeing to meet you in person. In your next and final letter, tell her that you cannot continue to conduct yourself in such a cowardly fashion. You must show her your face or cease all future contact. "Reluctantly," she will agree to meet you at the romantic outdoor lunch spot of your choosing.
All of you get up on the rooftop of the neighboring building to watch from above as she waits the hour you make her wait for her secret love to never arrive. The waiter, I assume you've already pulled him into the fold. Because he is integral in drawing tears from those cracked and decaying ducts. He should be quite obsequious when she first takes her seat, and then should grow more and more impatient with her as she waits for her friend to arrive before she orders. He should also have pushed at least two glasses of wine on her to make her wistful with memories of one of her weddings. You want the tears before the fireworks.
At the end of the hour, when she's just about to signal for her check, send in the decoy. An elegant man, 60 years young with the white ascot to prove it. He should approach her table with a radiant smile, almost certainly holding eye contact with her until there is only one last step left for him to pivot around her table and sit with the pretty young thing (one of yours of course) at the table just behind her.
That's it. She's done. She's ready to go. It's time.
First, the snipers. Kneecap shots only. Then get some boys to rappel down the wall and tie her arms and what's left of her legs to the chair. Wheel in the cage containing the sexual orgy of eight teenage runaways. Throw her inside the cage, making sure she's thrown right in the middle of the writhing mass of teens paid to copulate. When all of the teens have come, set them free from the cage and toss in the rabid starving mongooses. Make sure you all gather around the cage and laugh really loud while she is nibbled to death.
One word of caution. As the "love affair" progresses, her heart will soften and she may even use her wealth to do some good for the first time since she can remember. This might make you rethink torturing her to death. I know I wouldn't be able to go through with it once I saw that she was just a lonely old lady wishing she had a little love in her life. Maybe you oughta stop thinking about rich old ladies and check the temperature of the heart beating inside your very own chest, Ebenezer.
Happy Taunt The Evil Millionairess With Letters Falsely Declaring Your Undying Love Day!