[Everyone] - Everyone would generally be aware that, for Toby Malkinson, 'money' is no issue. The wealth of the Malkinson Estate is significant, but he is a frugal and does not flaunt it at all aside from his personal fashion. The fact he makes the effort and expends the time and energy to maintain his volunteer work and part time job are because of the rigorous requirements of his grandmother's upbringing, as well as his own personal interest.

[@Expendable] Samantha "Sam" Igorina Semenova - Sam was probably the second person he met when arriving at Sanctuary Hills. He would have needed furniture. However, I do not believe they would have interacted intimately or frequently unless they crossed paths in the town itself while he was working at the coffeeshop or awaiting repairs on his car. A possible angle would be his fascination with her magic; if she was willing to talk about, experiment, or otherwise just show it off he would have gladly observed and spent time with her on that subject.

[@naomimyselfandi] Aoife Fitzgerald - Toby, being a liberal arts student, likely has had little [b]professional[/b] reason to seek out or engage Aoife. Her reputation on campus is known to him, of course, and any interactions they have had would have been either in passing or in relation to their mutual creative writing interests. If they have any further relationship at all, it likely hinges on this aspect; Upon hearing about her (official) published works, he would have voraciously hunted them down and questioned her on her methodology and literary style, as well as ventured to ask for help in things like developing his pitch and cover letter. Perhaps, somewhere in the rabbit-hole of Message Boards and BBS fanfiction zones, they've interacted without even being aware that it's the other? If so, then she may even know of the fantastical occult writings of the [i]Mystical_Malkontent[/i].

[@shagranoz] Rose Blossomdew - Toby has likely run into Rose while volunteering at the library. She would find that his voracious appetite for all literature extends into her own area of interests— but that he, strangely, refuses to practice the magic himself or admit that he has a fascination with magic at all. He would, conversely, absolutely encourage and try to get her talking about her own interests on the subject, and any discussions he engaged with her on this front would have been fronted as 'for the sake of my writing'. At first blush, I don't have anything more in mind than 'they've met in passing, and he chats with her at the library'.

[@Gisk] Georgia Patricia Keen V - Toby met Georgia when he first came to Sanctuary Hills. The 1946 Rolls Royce Silver Wraith that Grandmother Lorelei had given him as a highschool graduation gift had broken down— over fourty years sitting in a garage with no maintenance will do that to a luxury car. Thankfully Toby arrived in town safe and well, and the two met after he had to have the vehicle towed. He seems keenly aware that her soul isn't truly in her work; he has made it his goal to always try to pick her mind for her own cleverness whenever he's got a philosophical conundrum or wants an outside opinion on practical things. This means that he writes her letters (like the anachronistic madman he is) or pops in to say hello frequently even without car issues.

(just adding this one for funsies, to round out my NPC interactions) Lea Arnaud, Magical Arts major (Specializing in practical evocative arts) - Toby's ex-girlfriend and he maintain a cool distance. From Toby's side, he desperately hopes his wild and frantic desire to avoid her at all costs isn't as obvious as he feels it is. He met the young Magician-To-Be in a philosophy lecture, and they hit it off initially. However, over time, his inability to establish boundaries permitted her to take advantage of him and the relationship developed a deep toxicity until the prodigal witch broke it off with him after an argument about magic finally pushed them both over the edge. It's been a year, but Toby is still awkward around her, and honestly isn't over her yet. The only positive from the relationship was that whilst burning the candle at both ends to try and keep the demanding woman satisfied, his muse was hyperactive and the misery of the relationship stirred his writing to the most progress it had ever experienced. Objectively, they were bad for each other- but don't tell them that, they both need some growing up.