#and then i'll have time to start posting Serious Mistakes coz I'm about to be on break
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@mareenavee you definitely got that right, Sydari is 100% Thieves Guild.
I like to think she's a bit conflicted over stealing from refugees, particularly when she's actually built her fortune, runs half of Riften and makes a "leave the downtrodden alone" rule. However, there was a period of time (between the whole sleeping in a warehouse in Windhelm and her eventual escape from their prisons) where the class of her marks didn't matter as much. She'd rob anyone who had some bread or a pair of shoes. Though she was pretty skinny and malnourished then, I don't think she'd pose much of a threat in direct combat. Her way of doing things means you won't see her coming. She wasn't arrested for thievery.
If she tried to rob Nyenna in that state, and Nyenna was just out of Helgen she'd probably go for a quiet pickpocket or a camp raid while everyone was asleep. If she's noticed she bails. If Nyenna had already come into her power as Dragonborn, she might still have tried something but I don't think she'd have been successful.
Once she starts actually amassing a fortune she loses that sense of desperation from her adolescence. So she really just starts going for planned heists and high-risk/high-reward valuables. She still won't show herself to the people she robs, you won't know it's happened until you get home and realise half your stuff's missing. Nocturnal still favours her so she uses the shadows to her advantage. Large homes with lots of valuables on the rich side of town beware. She did rob some of the Companions, and she thinks the look on Farkas' face after she stole all his gold is hilarious. She's a faceless nuisance, everyone with shineys has been hit by Nightingale.
However, she does also bully rival guilds, pirates, and bandit clans into working for her or risk being obliterated. She expects them to pay tribute in exchange for the freedom to raid (so long as they abide by her rules). I don't think Nyenna would encounter that side of her, since outside of her interactions with the guild (which puts her in positive standing with them), she doesn't really pose any threats to the movement of her people. I do have Sydari increasingly spending more and more time on Solstheim, she made very strong connections with the people of Raven Rock and it feels most like home (she also runs the guild from there but most of what she does is invest in plundering tombs for unique valuables). She's calmed down a lot at that point (assuming we don't make her Dragonborn since that complicates things), she'd probably be hanging out with the crew at the Netch. I'd say she'd start offering Nyenna unsolicited advice on travelling outside the Bulwark. She's found that there's more ash spawn lately and they are quite deadly if you don't know how to maneuver around them. She'd probably end up offering to train her in the art of being a literal shadow. Maybe Nyenna can help her with magic, she's got three spells that she can pull off and awful magicka reserves. Neloth would completely disown her if she wasn't at least talented with enchanting. She doesn't respond well to his way of teaching.
If they are both Dragonborn then I think she'd be absolutely delighted that there was at least one more person like her that wasn't an amorphous Library Land blob bent on killing her. She could have an actual conversation about being a reluctant hero over drinks. Talk a little about why dragons are constantly appearing just to get their souls consumed. The only other "legendary hero" around won't actually talk about anything unless probed (I write him as very hesitant to talk about that kind of thing). She wants someone to talk about hero stuff with that isn't a grandpa dragon, a grandpa monk, a grandpa archivist or an angry mum blade (they are technically the same age but I like to think elves mature differently). She'd be happy.
Random prompt for my fellow Skyrim enjoyers:
How do you guys think your Skyrim oc's would react if they were in the same universe together?
Just a wiiiiiild thought I had recently lmao
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