Hi! Sorry this is so late. Just getting back into things after a really awful week of exams.
Okay, so, Amelia!
CAYLIE works with her at X-Factor. How long has Amelia been working there? Caylie's been there 5 and a half years, when she started as the office manager, and then learned the business and got her PI license. She's very sweet, but Amelia's looks and personality could definitely rub her the wrong way. Billy's her best friend, so she can put up with the vanity and attention-seeking to a point, but when the two of them start bouncing off each other, Caylie probably looks for any excuse to get out of the office. But since Amelia's her co-worker, she probably falls into the camp of people Caylie will give a million chances to (she either forgives you unconditionally, or she holds a grudge and never changes her mind - that's pretty rare). But she can be judgy at times, especially because she's all about control and responsibility.
DEAN is the same age as her. She'd likely remember him from high school as the big class clown, very goofy. He's really good friends with Billy and Caylie so lots of opportunities for them to keep running into each other. I don't think he's bowled over by her vainer, shallower aspects, but until hooking up with Gale, he was one of the more promiscuous members of the community - just, not within the actual community. He totally gets casual sex to make yourself feel better.
I don't think VIC, EVE, ASH, ALEX, or ERIC have any clear connections to her, either from age or from not being around while she was doing cool stuff. They're mostly easy to get along with, though Eve is more amused by her behavior than anything else.