Headcanon 13
During training with the class where they are up against Class 1-B where one side is the hero and one side is the villain, Jennifer gets separated from her teammates due to the other opponents teamwork by splitting them up, while she's trying to find them, she comes across Shinso, the one student that not just some of her classmates have told her about but the whole school. They had warned and explained to her about what his brainwashing quirk can do and she made sure she wasn't gonna fall for it by not answering him.
They get into a combat fight while Shinso is trying his best to get her to answer him by saying things that would get under her skin, such as she'll never learn to control her powers and all that but she knows that he's just saying all that stuff to get her to answer him so he can use his quirk on her. At one moment, he says something to her that gets really under her skin and she wanted so bad to say something but she held herself back and "replied" by blasting him with her electro ball move, knocking him unconscious.
After training was over, lunchtime wa here and Shinso walks up to her and tells her that he's impressed how well she fought him during training today and even compliments how strong her power is. She looks at her friends then looks up at him and says, "Um? Thanks I guess?", then he tells her next time, he will beat her during training by coming up with something that will be getting under her skin so bad that she would recklessly answer him and use his quirk on her.
He walks away from her and her class's table without a care in the world while Jennifer thinks he's an odd but interesting guy.