I think it'll be fun if the two knew each other before the start of the game! Ainsley has lived in the city her whole life but comes from a middle-income family and was very focused on her own interests growing up (stars, looking after kids, reading) and wouldn't know him right off the bat as a result. Maybe she's heard of his family's last name from the more well-established newspapers she gets for herself but doesn't put two and two together. For some reason. (Ainsley please…)

She would definitely visits the animal shelter a lot, partly to volunteer and to see if there's someone she can adopt - Preferably a dog to keep her company! She would also try to reach out to him if she was able to notice how he much enjoyed looking after the animals there, serious face or not, or, at the very least, ask for his ear so she can happily chatter on about her time with the kids she teaches because she loves to teach. If she visited the shelter enough times, I can imagine she would bring things for the volunteers during the holidays/breaks as a thank you for all their hard work!