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The Wingman
Chapter 1 - Planning Session

Chapter 1 - Planning Session

“Ok we need a plan,” Jack said after they had finished their match. “You mean you need a plan,” replied Aaron with a smirk. “Dude please, I need this.” Aaron rolled his eyes, and after thoroughly letting Jack know how stupid this was, asked “Can’t you just ask her out without any prep just go for it, clean communication.” Jack gave Aaron a look that gave off the vibes, “Do you think I’m an idiot or something?” The answer was yes obviously but Aaron didn’t vocalize it.

“And what do you think my chances are if I just straight up asked her?” asked Jack, already knowing the answer. Jeremey and I didn’t need to say it to know he had zero chance ending up with Jessica. “So here’s the plan, in almost every childhood friend trope that succeeds the other guy is either a massive tool bag or the girl keeps ending up in randomly romantic moments with the childhood friend and realizes they loved them all along, right?” Aaron asked, making eye contact with each of his friends. Jack nodded his head already getting the idea, Jeremey was also nodding but Aaron knew he didn’t understand squat. “Now those are books, and these are real people we’re dealing with, but the idea should still work, which is why one of us is going to do some digging into Derek and the other will help Jack bump into Jessica.” Jeremey raised his hand and added, “Shouldn’t one of us watch Jessica to track her progress with Derek and prevent progress from happening?” Jack furrowed his brow and agreed but Aaron brought up a slight issue, “Do either of you want to stalk a girl and get arrested cause I don’t.” Jack and Jeremey didn’t know how to respond and there was a solid minute of silence until Jack finally had a thought, “What if we ask Jessica’s Mom first, you know that way we have some form of permission,” added Jack weakly. “Says the person who’s already semi stalking Jessica,” mumbled Jeremey. Aaron had to agree, “You know asking for her Mom’s permission and not asking her will just tick her off. Do you even care about her feelings? And what kind of parent do you think would let a boy stalk their daughter” Jack turned red and quickly apologized looking like he wanted to die in a hole. “Welp I’m going to ask her Mom,” Aaron said casually, getting ready to set off. “What!” Jack screeched, “You just told me that was a horrible idea!”

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Aaron smirked, “It’s all in the way you ask the question.”

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Anna Myers opened her door to see a thin red headed young man whom she felt she had met before. She was about to ask what he was doing there before he interrupted her thought process.

“Did you know that your daughter has been meeting a boy she likes, like LIKE LIKES, in private.”

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