Gabrielle

Gabrielle is a highway bandit who becomes an ally of Devon, either from him saving her or simply due to bumping into him at the inn where they stayed the night.Gabrielle is an orphan who is out searching for an item that will reveal her real lineage but every time she gets close to one, it either disappears or is revealed to be a fake, causing her to start losing hope. Devon tells her that while he can't help her, per se, he hopes that she'll find the item she's looking for and promises to stick with her until she does. She's grateful to Devon because of this.

Affection

 * Bild 2021-03-09 232018.pngg your first encounter with her, choose the suave approach. She'll get turned on by the mystery and increase her affection by one.
 * While camping, speak to her and tell her that she got plenty of experience to increase her affection by one.
 * The second time you speak to her in the camp, say that she's not as bad as she thought herself to be to increase her affection by one.

Meeting the Bandit
After escaping from Darkthorn Keep, Devon sets up camp and overhears someone sleeping. He ignores it at first, but soon, a bandit appears before him, saying that she is going to rob him. Devon asks if she has ever robbed someone before - successfully, that is. Because he seriously doubts it.

Gabrielle gets annoyed and tells him to hand over his money with his hands in the air. Devon, understandably, asks if it won't be very hard to hand over stuff in that case, annoying her again. Choosing either to tell her your story or using the suave approach causes her to gain +1 affection and decides to leave Devon alone.

The Second Encounter
When going through the Windy Canyon, if it's during the daytime, right as you reach the ending, a short scene will trigger. Choosing to go back makes you advance the Heroic route, ignoring it advances the Renegade route.

If you choose to investigate, head back to the Werewuffie's Cabin and you'll see a short scene. Either ignore it for a CG or decide to bust in, gun's blazing. The latter leads to a simple fight against some Werewuffies. Regardless of choice, Gabrielle joins you at this point.

If you choose to ignore it, head to the Highland Inn and spend a night. If Gabrielle is brought with you, there's an extra CG during the scene.

If she didn't join you, she'll instead be waiting outside as you exit in the morning, deciding to join Devon's team at that point.

The Drowned Castle
Late into the game (might also be based of Gabrielle's affection, I'm not sure), speak to her either in castle Warrengard or in the camp. Either way, she'll say she has a favor to ask of Devon. Agree to it (+1 affection) and she'll ask you to meet her in either Whitehaven or Port Ronod (I have not done this one for a while, I need to check it up on a fresh file). Speak to her on the ship and you'll head to what's known as the Drowned Castle.

During this segment, you'll only have access to Devon and no way to leave. Make sure you're fully prepared before comitting to this.

Once you reach the door, Gabrielle will enter. Follow inside and you'll see she disappeared. Heading straight up will do you no favors as the door is locked, so head left. Don't bother with the right side unless you want a couple of treasures.

Keep going until you eventually reach a treasure that contains an Orb. Bring it with you and you'll see enemies have started to spawn. They always spawns alone and are rather easy, with all of them being undead so they're weak to Holy. Head back to the main corridor - the first room you entered. Yes, I'll wait. You're there? Okay, cool.

Head to the door on the upper side of the room that I told you to ignore 3 sentences ago and use the Orb on the door. It'll open and lead outside. Head outside and... you'll encounter Gabrielle, who is just as confused as you are right now. Head on inside to the next room and you'll see a short scene. After it, ignore the treasures on the left - Gabrielle will work on those. Only one treasure works on the right side - the other one is rusted shut, so you can't really miss anything.

Once you open the other chest, Gabrielle will rush over and go over it, failing to find what she was looking for. Devon, confused, asks what she's looking for to begin with and she explains she's looking for an item that will point her to her actual family, explaining she grew up an orphan on Paradise Isle. Due to this, she's always been longing for a family. Devon expresses that he's glad that she told him... just as an Ultima Monster appears and chases them out. The two of them escape and Gabrielle plans on leaving without making up for the fact that Devon nearly died. She claims it's a joke and tells him to head to Four Season's Inn.

So, head there. Once there, head to the reception and speak to Gabrielle. Watch the scene and Devon will remark that all he had to do to get to this point was to risk his life and get attacked by a ghost in a haunted castle. It was totally worth it, though.

After this scene is complete, you can invite her to your room in Castle Warrengard with all options unlocked.

Trivia

 * She's 30 years old.
 * She calls Devon "The man of her dreams".
 * She's seemingly a bad bandit, rather often failing to get to the prize she wants or getting stuck somewhere.
 * For instance, at one point, she apparently got trapped in a dog door when trying to rob an unknown location.
 * Using the suave approach when meeting her for the first time causes Devon to remark that he usually gets called a creep for it, but Gabrielle finds it hot, which also increases her affection towards him.
 * She's normally wearing a mask to the point she disguises herself by removing it.