Olivine why are you trying to drastically change things again?
Seb has always been a point of personal ambiguity for me from day 1, always on the cusp of being something satisfactory. The previous outline hinging on the bookstore technically works, but isn't the most reader or visually friendly. Not to say that he should be all bombastic all the time, but that while we're struggling to come up with "interesting" scenes with him in his current circumstances, it would be easier in the long run to change things while also offering additional chemistry and similarity with Diana. Hence, videos. This also helps bring further of a foil to Yvonne, who handles East Coast affairs vs his more Californian based aesthetic.


Mandatory Facts
1) Seb currently hangs out at a bookstore he owns. It's far from the only business he owns. It's quaint and usually handled by employees he hires. Business isn't struggling. He may or may not enjoy it a lot.
2) Seb has an ex (that is a vampire?). If Bookstore-centered Conflict, this Ex is likely a doctor working with Main Doctor NPC. If Video-centered, perhaps in the entertainment industry themselves, if it makes for easier conflict. This ex is a good person and wishes the best for seb and vice versa, but seb still dreads seeing them bc the ex is miles above more satisfied and further in their life.

--- Bookstore-centered Conflict
Overall: Seb is looking for self-fulfillment, and is in denial about wanting to settle down and stay at his bookstore. Diana piques his interest

January:

End-of-year Conflict: The Ex comes to Sebastian and asks him to come with them for another adventure overseas. Seb, while initially willing to go, starts having second doubts because he really prefers the bookstore. (If romantic: plus Diana can't drop her schooling to just follow along.)

... I can't even figure out how to fill this one out.

--- Video-centered Conflict
Overall: Seb typically works in California creating entertainment videos in a company, particularly supernatural or media based ones with a team. Burnout/tedium/apathy eventually creeps up on him and he debates if it's time to drop everything and move 100% onto the next hobby like he usually does. These "flings" last anywhere from a few months to multiple decades due to the sense of time. Even on vacation, he can't idle for long, and opts to take a more hands on approach to one of the other businesses he dabbles in - a bookstore - to help pass the time as he tries to sort himself out half-heartedly. Likely works solo, but realistically would be working with a team (perhaps doing someone on that team a favor, serving as a charismatic face for the camera but also having enough knowledge to work variety shows and manage odd jobs) even if we can't realistically have them show up in the game.

Cons: If he works corporate, that means he's again under someone's thumb willingly or not - but on the bright side, as in real life, with his amount of clout he could barter successfully to keep ownership rights to his content not unlike The Try Guys. If he does comedic videos like Sexiest Vampires, this hampers his own ability to publish more serious work potentially, but that may not be a goal of ours at all. If he works indie, this makes it harder to find some sort of conflict.

January Conflict: Diana is the one who wants to host a campaign after finding a guide book in Sebastian's shop. While she does drag the others into it
Diana may want to video tape all the stuff that goes down in her month, including Sebastian's DND session. His ex arrives and he's more terse than usual because he's objectively not changed since when they broke up, however long that's been (because any time is long enough for him). A bit of a passive slow burn conflict, not sure if useable.
Why DND? While Seb is flippant, we don't necessary have the opportunity to really get invested or see it on screen until January's proposed scenario. Show, don't tell. We know from November that Sebastian has a lot of experience in a lot of fields, but DND can let his trivia really shine but also show his investment as well as Diana just for him to... promptly drop it. The EX arriving and potentially somehow getting involved in this allows us to have reasonably explanation for why this breakthrough/reveal would occur at this time, as well.


Types of scenes: Can become Diana's video editor/assistant when she tries to find one and helps her push things to a more refined level to match her current popularity, can cause more ripples if he shows up in the background of Diana's videos (we have to mention seb clearing it with HR and/or his contract if corporate.) If recording videos even during sabbatical (why?) then Diana can assist him with that. Excuses to look more into vampire/supernatural lore.

End-of-year Conflict: Seb's sabbatical comes to a close and he has to decide if he outright wants to quit his job and try a new random gig to get that initial rush again, or continue working on something after the initial excitement wears off. He can also serve as a foil to Diana's own conflict about throwing herself entirely into her makeup channel or not. Seb's Ex may be part of the conflict.

--- Both
While there may be the risk that Diana comes off as a manic-pixie-dream-girl figure, it's the opposite because she'd be encouraging him to stick to his current stability.
Similar to one of Diana's potential career paths - stick with Marketing after gaining a new perspective and desire on the topic.
Potential conflict about long term distance relationships and overall viability of it.




CONFLICTS
Madison - Resolved before route lock. November spotlight, Feb reiteration. Platonic lack of communication, reiterated on a romantic scale come January/Feb.

Yvonne - Not resolved before route lock at all, only introduced. January intro, March/April spotlight. Too big fish in a small pond out of cowardice.

Forrest - Partially resolved before route lock. December spotlight. Insecurity about romantic prospects and jealousy of others, general anger towards vampiric circumstances.

Sebastian - Partially resolved before route lock.