Ohhh, yes. Haha, Jer and Jude have been friends forever, since they were little, so I definitely think Olive could know him. It's kind of unavoidable, since these two and Wes are all but attached at the hips. He's too friendly NOT to be chill with Jude's fam ;P
She is being as sneaky as possible about her extracurriculars, but she's already been caught once. Who's to say it won't happen again? But srsly, they can just have breakfast together and instantly click, really. If she has a Jude connection, there might even be a chance they've met, if Olive ever came to IUP. Since Sydney was dating Wes.
LOLOLOL, yes plz.
She could definitely know her from there. Brooke helped get Andrea involved in all that.