This is a work of fiction, inspired by a picture and caption on another site - my imagination on how the two could have gotten in the picture together.
He didn't really know exactly what he was looking for, just that he needed something that would work for the costume they were planning. So when the girl working the vintage shop asked what he was looking for Jack was honest in saying "I'm really not sure." and then they had a laugh and then they both paused and had a "Don't I know you" moment.
She figured it out first "Mr. Blake? It's Kylie Santos" She went to give him a hug so he reciprocated, even though she wasn't someone he was very close to.
"Wow, great to see you" he says, "What's it been 3, 4 years? You've certainly added to your piercings (she had them in her nose, on her lip and who knows what other places) Are you still going to school?"
She replies "Yeah, Mr. B, my mom wouldn't let me get anything until I was out of high school, and this year in the fall I'll be a junior at GSU, working on my art degree."
Knowing it's not the right place or time for the "Well that's not going to get you a job" lecture he skipped it and just said "Oh, that's great." He then proceeded to tell her what he was trying to find - something that would work for a group costume for the game "Elf Lord 8" that he and his friends were planning on making for the ComicCon in the city at the end of the month. "That's why I have the beard now, getting into character." So they both had different looks than what they were used to before, but she was still wearing the baggy sweatshirt and ripped jeans he remembered.
Her reply of "Oh, it looks great, very strong chin" seemed almost like flirting - it was tough to tell with these emo chicks, her totally black hair and almost scary make up made it a mixed message. She showed him around a few different ideas and he left with just about a full costume, but he would need a belt and a certain hat to make it complete. She told him they get deliveries of new stuff every Thursday, and if he wanted she could let him know if she saw anything that would work. He left his number with her and thanked her for all her help and went on his way, not really having a second thought about it.
That was until later that week when he got a text from a new number with pictures of a couple fancy hats and asking "would any of these work?"
He replied "Hi Kylie, I like the 3rd one, but it would need the red flair on it." He then made sure to save the number as her and she replied.
"I have a lot of fabric here and I've gotten really good at using the sewing machine to fix things around the shop - let me see what I can do." "Thanks!"
The next day she sent a pic again "done" and it looked great "Awesome, thanks so much!" he replied.
"U dont alwys have to youse capitals and punctuation, u know lol"
"Okay." He responded.
She gave him the facepalm emoji and said "Once and English teacher always an English teacher - it is the summer u know"
They then made plans for him to pick it up that Friday.
When he got to the shop, they had another nice conversation, and when he asked how much he owed she gave him her store discount - and he asked how much for the sewing she did and she said "On the house, but I do have a favor to ask" He was intrigued. She asked about the group going to ComicCon and she told him one of her art classes had been about stage make up and costuming, and she had done the make up for several people who went to a show last year, and showed him a couple pics of her work.