Get to Whiterun, it’s the nearest town to the point where you exit the starter dungeon. Search out the man sat in a horse and cart and ask him kindly to travel to Windhelm. It’ll cost you twenty gold but that’s a much better option than walking across three quarters of the map.
Walk inside the city, past Candlehearth Hall, and search out an NPC named Suvaris Atheron which is having a discussion with an NPC child. Usually they’ll be talking right outside the house of Aventus Aretino but we’ll get to him in a bit. After you’ve talked to her, she’ll explain a child is trying to carry out a ritual to summon the Dark Brotherhood into town – this is your cue.
- Head to Aventus Aretino’s house on your map. A quest called Innocence Lost should have popped into your log. Talk to him as he’s enchanting and he’ll tell you he wants to get rid of a mean orphanage owner ironically named Grelod, The Kind. She’s housed in the Honorhall Orphanage in Riften. If you can’t quick travel there after exiting the house, simply exit the city, talk to the man in charge of the horse and cart and he’ll ferry you there for 30 gold.
- Once inside the orphanage, located towards the north of town, listen to Grelod bully the children, just so you feel a bit better about the forthcoming murder. Follow her into her office and kill her any way you see fit. She only takes one hit to take down and it’s impossible to do it without the kids seeing, so don’t worry about warping their fragile little minds. As the little urchins talk fondly about their former torturer’s demise, exit the building and fast travel back to Aventus Aretino’s home to tell him the good news.
After you’ve made this kid’s Christmas, exit the city and fast forward time two-days by waiting near the main city gate. Once forty-eight hours has flown by in a matter of seconds, a courier will then rapidly approach to give you a letter. This spooky note simply reads, “We Know” with a giant black hand emblem – yay, you’re about to make some new friends. The Dark Brotherhood has noticed you, but now you need to make yourself vulnerable so an agent will emerge.
How you do this is very simple; sleep. Walk back into the city, enter Candlehearth Hall, ask about staying in a room, enjoy the land of nod and you’ll be awoken by an agent of the Dark Brotherhood; thus beginning your internship with the guild. Easy peasy!
Now we would help you with the next bit, but honestly it’s both awesome and self-explanatory, so really you should just experience it for yourself.
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