After her conversation with Lily, Karlie immediately returned to Taylor's side. During the next stop off at Taylor's locker, Karlie "borrowed" a pen and notepad to jot down every perceived or confirmed interaction she's had with Taylor thus far.
Karlie stares intently at the piece of paper in front of her waiting for a pattern to appear. Nothing is instantly jumping out at her so she starts from the beginning, re-reading the notes she's jotted down.
Her focus is broken and she's instantly nervous when a communication begins from Ms. Wintour. In this moment, Karlie wishes that communicating with angels wasn't done in such an archaic fashion. She's watched how quickly Taylor and her friends can send messages. She waits in anticipation as the familiar tingling is burning its way up her arm, symbols beginning to take form.
*%<><<<>_+_*+*#^^^#^()()_==/>/> (Today.7:00pm. Negotiation.Contract.Moving.) As Karlie reads the message, she breathes a momentary sigh of relief at the realization that Ms. Wintour seems unaware of Karlie's recent transgressions. Her relief is short lived; however, when she translates the final word: Moving. This is not going to go over well with Taylor... not.at.all.
Andrea and Taylor are furiously chatting in the front seat. In great detail, they go over the songs Taylor will sing at the meeting and they practice answers to questions that may come up during any negotiations. Most of all, Andrea is repeatedly reminding Taylor that she doesn't have to agree to anything and that no matter the outcome of the meeting, Andrea is so proud of her. Knowing Andrea will be supportive either way makes Karlie feel less guilty about what she may or may not have to do an hour from now. She knows Taylor must sign her contract. The course is already set for her and if she veers from it, Karlie will gently, or if necessary forcibly, nudge her back on course. Karlie only hopes in the end it's what Taylor wants-that it brings her happiness.
Taylor is everything Karlie knew she would be. She's charming them and they see the talent shine that Andrea and Karlie have witnessed for years. Karlie beams with pride, wiping a cold tear from her cheek as the music executives offer her a contract. Karlie knows her path has been decided, but the intricate details unfold in front of her just as they do for Taylor. Karlie didn't know she could be so happy to see Taylor smile as they tell her they are prepared to put together her first record. Just as Karlie is about to celebrate what a cake-walk of a meeting this has been, Mark, the VP of Marketing speaks up.
"Taylor, Andrea, there is one other thing we'll need to discuss. We'll need your family to relocate to Nashville."
Here it comes.
"Whaaaaat? But why? I don't understand. I go to school here. This is my home. My friends are here."
In a firm voice, Andrea attempts to navigate the situation. "Taylor." She looks up meekly at the four men in the room. "I'm sorry gentleman, can you give us a moment?"
Taylor and Andrea excuse themselves to the hallway with Karlie only steps behind them. After a five minute pro-con debate and an impromptu family meeting over the phone, Taylor has the whole family's support to sign the contract. It is clear by the anguished look on her face that even with their support, Taylor is still torn. After a long pause, she looks to her mother and asks for a quarter. Perplexed, but without any badgering questions, Andrea searches in her purse until she pulls out a quarter, dated 1989. Taylor rolls it between her fingers twice before flipping it up in the air. Karlie knows it's about to land on tails and the problem is, she needs it to land on heads. With a quick flick of Karlie's finger, the quarter lands in Taylor's hand, but then bounces to the ground. She looks down and then looks up at her mother as the quarter faces up, on heads. "Well, Nashville it is." Taylor slowly stands up and embraces her mother tightly.

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Guarded By Fate
RandomKaylor AU in which I try to answer the question ... What if, instead of a VS Angel, Karlie was a literal angel?