Main Characters are always prioritized. They are guaranteed at least 1 - 2 story events per update unless something bad happens. Side Characters have less of a priority, which is why they sometimes don't get updated. Background characters are on another level of priority, characters like Ann, Peni, Sarah, and Juliet may only be used for sex and appear in other character's stories.
Oh fuck I forgot about Juliet, heck yeah anything with her would be great, she appears in background plenty as is so she's developed to the point where some direct interaction would pay off, already happy enough though that she acknowledges you at the college :)
Not a big tiddy guy myself but shy, glasses and fairly goth, unf <3