The Thieves Guild of Skyrim mostly consists of douchebags. There, I said it. I know it’s a weird way to start an article, with the conclusion at the start, but it makes oh so much sense.
Okay, let’s backtrack. Let’s look at why they’re all douchebags.
The first time you meet the Thieves Guild, it’s most likely via Brynjolf. He’s a shady but attractive looking guy claiming to sell miracle cures that people are dumb enough to buy, in the market square of Riften. He’ll always spot you and gesture about how much gold you have, before asking if you want to help with an actually somewhat tricky ‘initiation’ mission. You can refuse this quest and go on your way, but you’ll need to speak to him eventually in order to complete the main quest line.
Brynjolf though is the nicest guy in the Thieves Guild. Apart from the end of the Thieves Guild questline where he bugs out and only ever says that he doesn’t have time right now, Brynjolf is mostly alright. He has some concerns about you. So does Delvin, who’s the old, somewhat kind pervert of the guild. But that’s about it. Vex and Dirge in particular are major douchebags, and Tonilia is such an annoying bitch who acts as a fence and claims she isn’t a member while wearing Thieves Guild armour.
You can tell how much they like you when they send you to steal information from Goldenglow Estate, a place so well locked up that their pro thief Vex couldn’t get in there. Everyone expects you to die, although not nearly as much as the people behind the initiation quests for both sides of the Civil War. Of course, when you do come back, everyone loves you for about five seconds. But then it’s back to scorn.
It takes getting right into the depths of the guild to find anyone who likes you. Etienne Rarnis might like you if you saved him during the main quest and didn’t pretend to be a Thalmor interrogator. Rune knows fuck all about his past and feels a bit like an unfinished NPC. Vipir the Fleet has an amusing story. It seems like all the douchbaggery is only present at the face of the Thieves Guild.
Which is odd really, since the Thieves Guild storyline is more about bringing the family back together and bringing luck back to the guild. You improve various relationships with allies of the guild, from the traveling Khajiit merchants, to a shifty Argonian, to the horrifically smug bitch that uses the Jarl of Riften like a puppet and keeps the Thieves Guild safe from their inept guards and everyone else. I mean, you spend a lot of time being the chosen one and putting everything back together, but it’s more because of your own skill and less because an aedra or a daedra is looking at you funny. Okay, later on you get a blessing from Nocturnal, but before that, it was mostly because of your own pure skill.
Plus, Nocturnal doesn’t give a shit anyway. She just wants her damn key back.
There are more exceptions though. Karliah, the person everyone believes killed Gallus (the former guildmaster) is genuinely quite nice. Even when everyone considers her (and later you) a traitor. After all, she could have left you for dead inside that stupid dungeon, but she didn’t.
The last two examples I’ll bring up are Sapphire and Glover Mallory. Sapphire is a unique case. She’s incredibly angry and antsy and she clearly hates everyone, but she DOES have a valid reason. Her past was fucking awful and after the first time I asked, I never asked her again. Yep, I felt sympathy for a video game character.
Glover Mallory though is a bit different. A bit like Sapphire and Brynjolf, he spends more time outdoors. In fact, he’s all the way in Solstheim. But even if he doesn’t know you’re part of the Guild, he’ll still look after you. Genuine nice guy with a bit more depth than the guys in the cistern. And he also gives the guild a bit more of a third dimension, because, like all guilds, the Thieves Guild is very, very two-dimensional.
The rewards though are some of the best, so it’s a guild worth doing. Exquisite armours, lots of loot and, most importantly, fences in every city. Seriously, it’s worth it to finish the Thieves Guild, as those fences with 5000 gold each are really valuable and make life so much easier.
You just need to push through the douchebag front of it all.