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ACT I: ROMANCING THE ROGUE
Note: It is necessary to select the topic with ALL CAPS in the romance quest described here, or any option from the dates in ALL CAPS, to opt-out of the romance and onto the Just Friends path. This is worth doing if you don't plan to romance Val, as it unlocks some unique friends-only content and lines.

• Once you've completed Stand by Me, wait a couple of hours in-game to let Val's somber mood lift a bit.
• Select the new dialogue topic asking Val if he ever thinks about the two of you. He does indeed and asks you on a "date" to explore a ruin. Selecting the ALL CAPS option is the Just Friends route, and Val won't hold it against you.
• Head to Frostmere Crypt. Resolve the opening scene with Eisa Blackthorn however you like.
• Val has a lot to say in here, starting at the entrance. Don't rush. Keep an ear out for his attention-getting comments, then speak to him.
• His conversation spots are: outside the main entrance, the first gate you raise via pull chain, after you pull the lever to drop the bridge, just before you enter the cave with the Pale Lady, heading up the stairs to exit the Pale Lady cave, and on the bridge just before you leave the dungeon.
• Following the Ruins Date, Val will invite you on an optional date (Hidden Depths, covered in Side Quests Article). Accept, delay, or decline and follow the journal instructions accordingly.
• Once you've resolved the Lake Date, read the quest instructions carefully with respect to what item to equip, where to go, and what time of day. This is by design so that you the player control the timing of the romance progression.
• Equipping the Amulet of Dibella at night kicks off the next big conversation. This is the branch point for the type of romance you want to have with Val. The choices are Innocent (sweet, not physical), Kindred Spirit (an impulsive night then navigating how to be more to each other than a one-night stand), or Rivals (you easily misunderstand each other and there's drama).
• Regardless of your choice, the next morning you should speak to Val.
• Head to Whiterun marketplace during the day for a change of pace. If Nazeem isn't there yet, just give him a minute or two. Val will start some trouble once he shows up.
• Talk to Val about what you just witnessed and decide how you feel about it. If Nazeem was dead for some reason you can talk to Val right away at the Marketplace. Val will remember your choice about the ring and your thoughts on his habit of stealing.
• After some additional conversations, you will be at the Define the Relationship stage. Equip an Amulet of Mara; it's not exactly a marriage proposal but it will get Val's attention and make your point.
• Val will surprise even himself and confess that he's in love with you. You can reply in kind or not, and this choice will inform what happens in the next act.
• If you tell Val you love him, all will proceed smoothly.
• If you do not tell Val that you love him at this stage, tread carefully as it will be possible to break his heart forever in Act II.
  

• After the conclusion of Romancing the Rogue, you will have either told Val you love him or not. This will affect the options in Wicked Game.
• In a safe location at night, once you have completed Safe Harbor, a new dialogue option will be available to tell Val you're heading to bed. If you didn't tell him you love him, he won't have much to say. If you did tell him you love him, and depending on the romance path you picked, the interaction will be warmer. This is dialogue is not available at the College of Winterhold for continuity and conflict resolution reasons.
• Go to bed. Sleep. If you are busy getting abducted by the Dark Brotherhood, don't worry, this quest will pick up after the assassins are done interfering with your love life. This quest step is also paused while you are at the College of Winterhold.
• When you wake up, Val is nowhere to be found. Check your quest journal and read carefully as you go.
• Pick up Val's Ring from the dock at Safe Harbor. It's next to the small blood stain.
• Search along the northern coast for Val's sailboat. It's near Pilgrim's Trench.
• Three mercenaries are waiting for you at the boat. They stole your pirate boyfriend! Kill them! Retrieve the note from one of the bodies and Val's sword from the backpack on the boat.
• Read the note, then head south to the Sightless Pit.
• Depending on your choice way back in But You Have Heard of Me, either Tarek or Jena will be waiting for you. In either case, after a brief dialogue your only option is to fight to the death.
• Once Tarek or Jena is dead, hop down the hole into the Sightless Pit. Fight your way through the dungeon until you reach Val. He's got an objective marker on him. SAVE YOUR GAME HERE IF YOU HAVEN'T TOLD VAL YOU LOVE HIM.
• Speak with Val. If you have told Val you love him, the reunion is straightforward. Get him healed, he'll forcegreet you to get his stuff back, then exit the cave, and take the sailboat back to Safe Harbor to complete the quest.
• If you haven't told Val you love him, you will have the choice to either heal him or ask him to get up right away.
• WARNING: If you ask Val to get up right away without recognizing that he needs healing and is too proud to ask for help, you will potentially break his heart. This is conversation path is not reversible and can end the quest and the romance arc. Choose carefully here and as usual, ALL CAPS ends the romance.
• If you do break his heart, he'll be rather quiet for a couple of in-game days, but he'll get over it eventually and you guys can go back to being just friends. This will count toward unlocking the Just Friends content that is normally not available if you romance him.
• If you do heal Val first, this will lead to a less fraught conversation where you can tell him you love him and continue with the romance quest. Exit the cave, return to Safe Harbor via the sailboat, and complete the quest.
  

• Once you're back at Safe Harbor with Val, a new dialogue option to return his ring to him will be available. You can select it at any time; it will wait on you. I recommend doing it sooner rather than later as his outfit system will be a bit wonky until this is resolved. The exact wording varies by which romance path you took.
• After the experience in the Sightless Pit, Val has had a major change of heart about commitment. He's going to pop The Question. There's some banter, you can ask questions, or you can accept right away. You can't reject him at this stage because one assumes you'd have broken up with him earlier if that were the plan, you heartless monster.
• Depending on what your opinion was of his stealing the ruby on the Whiterun Market date, Val will give you an engagement ring or something simpler.
• There is an ALL CAPS option to decline Val's marriage proposal. This ends further romance quest advancement and is irreversible, but you and Val will remain lovers. You cannot talk to Val about kids if you make this choice.
• The quest Wing and Wing soft-starts in the background, and you can now discuss the topic of children with Val.
• From there you are free to discuss the wedding venue, either the Dark Rose or the Temple of Mara.
• If you picked the Dark Rose option, talk to Val to travel to the Dark Rose or make use of the Spring Rain's travel menu. Make sure you talk to him before you start the ceremony, as he has something sweet to say. As usual, he'll call out to get your attention so you don't miss it.
• The wedding is my interpretation of how a Dunmer ceremony might look. Azura is the prince of dusk and dawn, so Fathis will tell you to wait for dawn if you speak to him at the wrong time of day.
• Speaking to Fathis between 6 am and 8 am will allow you to start the ceremony.
• After the wedding vows, have a chat with Val, check out the cough-situation-cough in his cabin if you're so inclined, then tell Val you're ready to head home and start your new life together.
• If you picked the Temple of Mara option, travel to Riften and speak to Maramal. You'll get the familiar dialogue about holding your wedding the next day.
• Val will depart to prepare. The quest journal will prompt you when it's time to attend your wedding. It is actually safe to be "late;" the quest will wait on you.
• Watch Val have a brief scene with a surprise guest, then he'll call out to get your attention.
• Have a quick chat with Val before the ceremony, same as above.
• Speak to Maramal to begin the ceremony.
• Once you're married and done in the Temple, talk to Val to wrap up the quest and start your new life together.
• Val's wedding outfit is unlocked as a new option in his dialogue menu.
  

• Once you and Val are engaged during Making an Honest Man of Him, there will be a new dialogue topic about children. The exact wording will be different depending on if you have adopted children yet or not.
• There is an option to say you don't want to be a parent; this will conclude the quest, much to Val's relief.
• If you already have two children, there will be a series of conversations to give Val some words of encouragement and discover faith in himself about becoming their father.
• With two children already adopted, the quest will conclude once these conversations are finished. If you only have one adopted child, the quest continues in Windhelm.
• If you have no children yet, the conversations about becoming a parent are a bit different but also eventually continue in Windhelm.
• In all cases, the conversations are spaced out with an in-game timer of 3 days. The quest journal will prompt you when Val is ready to continue. You can take longer if you want; the quest will wait on you.
• After Val has worked through his fears about fatherhood with some help from you, he'll mention needing to go to Windhelm Market on business once you've gotten married. Take him there in the daytime and have a chat with Val once you arrive and are near Niranye.
• His banter at the Windhelm Market will be a bit different depending on your thoughts wrt to his stealing things, but after the conversation a Dunmer girl will attempt to sneak up on him and pick his pocket.
• The girl, Ravani, is caught red-handed but has plenty to say to Val and promptly adopts him.
• Val looks to his better half (you) for help and rescue.
• Speak to Ravani, get to know her a bit, and offer to adopt her. She is now following you.
• Ravani can be told to live in any inn or player home. Talk to her once you arrive to tell her this is where she lives.
• The quest concludes, and Ravani and Val will have a few random, cute interactions over time.
• You can also have a few brief conversations with Ravani, tell her it's bedtime, or that you want to her to move again which puts her in follow mode like before.
• Val currently does not have any scenes with the Hearthfire kids, and Ravani doesn't interact with them either. Maybe in a future expansion?
• There is nothing stopping you from adopting an additional child once Ravani has been adopted, including more with the Hearthfire Multiple Adoptions mod. Just make sure you don't have two kids already when you do this quest.