Hi Kenzie, welcome to the game! Sorry this reply is SO LATE omg. I'm Josie and I have four characters here:

This journal is Pippa Nightingale, a Ribbonfin sophomore and Hogwarts exchange student new to Gooseberry this year. She's a soft-hearted vegan pacifist and would definitely be up for helping Garrett with his animal charity work! As for Bailey, Pippa is ON A MISSION to snag herself a cute American boyfriend, so she may ask Bailey for help with that~

Henrietta Gray (unregrettable) is a senior and the new Azurcrest Quidditch captain, taking over from her sister who was captain for the last two years. She loves parties, flirting, and having fun, but can be pretty blunt. She'll be aware of who Garrett is via Quidditch and OE. And I think she'd be friendly to Bailey? Etta probably finds Bailey's matchmaking amusing as long as it's not malicious.

Coralee Wong (firecoral) is a Coppertale junior, and kind of a bitch although she tries to hide it under fake sweetness and passive aggression. Coralee is a troll who loves stirring up trouble for the lulz. I think she'll clash with Garrett, especially given that Garrett is also a prefect. But! I think Coralee would get on well with Bailey (which is saying something, because Coralee gets on with very few people). But if you're up for them being sort-of friends, then Coralee would encourage Bailey to stir up drama with her matchmaking, and sit back and laugh at the results with her.

Lastly, Irene Lovelace (interlacing) is an Ebonhide senior, and is pretty quiet and bookish until you get to know her, but sadly I don't think she'll have much overlap with either of your characters.