Awesome! I'm glad that sounds like something that could work out :) Olivia was pretty close to the previous Head of Health, so Charlotte would probably recognize her from her visits down at the office as well as could have gotten to know her as well. Like Joan mentioned below, she's dating Maizie so that would probably be something Charlotte knows about as well.
I just realized I never talked about personality for either of these guys. Olivia is a hyper ball of energy who works as a scout for the LBJ, under Nick at stadion, so Charlotte would probably be used to her dropping off supplies. She was out of commission from October to right around now, though, after a rival gang to the Hellhounds broke her ankle. (Oh, Charlotte would also know her from that, since she did a lot of checkups with the previous Head of Health). She gets along with most people, especially those who aren't really people she'd have any reason to compete with, so it sounds like your girl wouldn't be an exception to that.
Pete is kind of a fratbro outside of work -- if he was ever working with Charlotte in a professional capacity he'd be responsible and professional, but outside of that he'd probably flirt with her. He used to date Savannah, though, so I think he'd have at least a little good sense to not hit on her council too much.