I think Amanda did her share of spending time around the public school as well through her tutoring. So totally plausible that they had interactions there. I do like the idea of her and Theo being friendly! They can both buck the standard "jocks have to be dumb" stereotype together. Also, if she hadn't gone into architecture, Amanda would have probably gone into law. So I imagine they've got quite a few similar interests.
And I say yes to having had some interactions with Everett as well. As protective as she is of her stupid big brother, she 100% approves of Elle, so I think she'll like Everett by association.
Amanda is probably kind of hyper-focused at work, because the job means a lot to her and she wants to succeed. So he probably would have had to prod her into unwinding a bit at work. The swearing and the baked goods definitely would have helped put her more at ease in that regard. She is definitely not stressed about him being on leave at all. Nope.