Living the life of a rogue doesn't necessarily have to be a solitary experience. In The Elder Scrolls V: Skyrim love can be found in some pretty surprising places. There happens to be a handful of single ladies who wouldn't mind settling down with a roguish type.
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Finding a mate in Skyrim is a very straightforward process. If the Dragonborn likes somebody, and the feelings are reciprocated, all that's left to acquire is an Amulet of Mara. Future brides-to-be need not ask the shifty rogue where he obtained said amulet. These are some of the more understanding marriage candidates who may not mind wedding a more underhanded Dragonborn.
5 Muiri, The Vengeful Apothecary
Underneath Muiri's innocent exterior lies a rather dangerous individual. Much of her backstory is revealed in the Dark Brotherhood quest "Mourning Never Comes." She puts out a contract on the lives of the people who wronged her. Muiri's targets include a scoundrel named Alain Dufont and Nilsine Shatter-Shield.
In order to wed Muiri, both of these individuals need to die. If the player decides to grow a conscience and let Nilsine live, then Muiri won't be completely satisfied with the Dragonborn's work ethic. Her clear lack of morality makes her an ideal candidate for a pure rogue. From a role-playing perspective, rogues are often willing to do anything and everything in order to get by in life. If Muiri is fine with cold-blooded murder, then anything else the Dragonborn does on a daily basis should pale in comparison.
4 Ysolda, The Shady Merchant
For a rogue, the ends usually justify the means. Ysolda is a rather pleasant Whiterun merchant who can be found in the city market. She will be all too eager to tell the player about her fascination with the Khajiit and her unfortunate lack of mammoth tusks. Nevertheless, beneath her sunny disposition is a bit of a dark side that may upset more noble players.
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It turns out that Ysolda is involved in the trade of a substance called Sleeping Tree Sap. It's a type of drug that, in her words, "makes you feel as healthy as a cave troll." When her previous supplier is found dead the Dragonborn has the option to keep the business flowing. Ysolda will reward the player with gold every time Sleeping Tree Sap is delivered to her. Marrying Ysolda requires the additional delivery of a mammoth tusk, which will raise her disposition with the player. In the end, someone who is willing to deal in narcotics may get along quite well with a pure rogue.
3 Shahvee, The Incurable Optimist
Shahvee is a down-on-her-luck Argonian toiling away on the Windhelm docks. What makes her somewhat unique is that Shahvee is genuinely a decent person, albeit one with a checkered past. She is one of the many workers on the docks who will speak of the sad state of affairs regarding her people. Shahvee will also ask the player to retrieve her stolen amulet.
More specifically, it's an Amulet of Zenithar that will require some dungeon-delving in order to find it. Once it's returned to her, Shahvee will become a possible marriage candidate. Interestingly, she is the only female Argonian that can be married in the game. At the conclusion of her quest, Shahvee will admit that she used to be a thief and will even increase the Lockpicking and Light Armor skills by a single point. One would think that a rogue and a former thief would have a lot in common. Shahvee knows better than anyone else how morally gray the world can be, after all.
2 Borgakh, The Steel Heart
Borgakh the Steel Heart is a young Orc warrior looking for adventure. And who better to lead a life of adventure than a rogue? Borgakh can be found within the Orc stronghold of Mor Khazgur in the north of The Reach. She dreads the day when she will be married off to an Orc chief without first experiencing life on her own terms.
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The player can actually solve both of those problems rather easily. Convincing Borgakh to enter the Dragonborn's service with a Speech check unlocks her as a follower. She can experience as much excitement as she wants by accompanying the player on his/her many adventures. And, rather than marrying an Orc chief, Borgakh can wed the Dragonborn instead! It's a win-win situation for both parties. From a practical standpoint, having a skilled warrior by one's side for protection isn't a bad idea for a pure rogue.
1 Brelyna Maryon, The Enthusiastic Apprentice
Brelyna Maryon is a Telvanni mage currently attending the College of Winterhold. She is someone who is always trying to test the limits of her abilities in practical ways. Brelyna often expresses a desire to get out of the classroom and test her theories in a more hands-on manner. Someone as worldly as the Dragonborn is just the right person for her.
Her associated quest, "Brelyna's Practice," is done in the interest of that goal. The player doesn't need to do much other than stand still and allow Brelyna to cast her spells. The results fail to meet her expectations, but helping her out unlocks her as a follower and a marriage candidate. Dungeon-delving with a mage often isn't a bad idea when playing as a rogue. Her skills lay in Alteration, Illusion, and Sneak. For a stealth-based character, having Brelyna come along for the ride can come in handy on more than one occasion.