Ok I think I have some ideas
heart Jessie/Pompeii
-Since he is a part of the book club maybe he can come in the store looking for books to read ^.^
Abby/Ellicott
-Fighting a chibi can be interesting. All the fights that Ellicott have been in has had others intervene so it would be interesting to see how she handles herself by herself... and her large dog, Sherlock ^.^'
Quinn/Havasu
-Both him and Quinn go to DCU. Maybe they can meet there
-Generally running into each other, Quinn takes his savanna cat out for walks so maybe they can meet that way
Dessie/Antares
-Dessie busks when she gets a chance and the weather is good so that would be a good way to meet.
-She has also traveled across the country and probably spent some time in SanFran
--Be warned though she doesn't like being touched and will deck him if he does
Pat/Tortuga
-Park meeting?
-If your boy gets hurt during a fight Tortuga might patch him up if you want, it could help teach him that not all order are 'evil'
Civi Dawn
-Dawn is an outside girl... loves skating and animals so they might run into each other at the park, literally >.<'
Guardian Cat Mel
-Meet the not too bright cat during a night patrol or something. The cat likely wouldn't attack... well can one really count a cat pouncing on them an attack? I think it would be mostly curiosity on Mel's part XD