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Octavia has a complicated life. She was enslaved, and she and Reg are rescued by you. All they had up to that point was each other. They were thrust together and needed to survive.
As you adventure with her, you need to drag the orc POS along so they can have discussions. In act II you usually get the tavern scene. Depending on how you have treated Reg, it can be a solo with either, or a threesome. I dispise the orc, so it was clearly a solo with Octavia.
As you adventure, take every opportunity to talk to her, take her to your chambers, and generally be a good guy or gal to her. Do not rise to her baiting you to react when she flirts with other folks.
Also, it works best to choose any dialogue which supports freedom, free will, and treating people well, which is generally characterized as chaotic good/neutral good.
Now for milestones-
She and Reg will break up. She will be sullen but happily go with you to your bedroom.
She will at some point ask you to run away with her. (WITHOUT the Orc)
If you say yes, she will give you some very sweet dialogue, but basically says you all have to stay as the others will be lost without you both.
She eventually tells you she loves you. Could be before the above, but definitely after.
Shortly after this, she and Reg will break up. Talk to both. The both say they will always be friends. Reg convo is interesting in that you can apologize for taking Octavia away from him. It is good stuff.
When Octavia and Reg get their personal quest next steps to discover who sold them to slavers and why, Octavia stops going to bed with you. Fear not, as long as you do not screw things up, this will correct itself when you complete her quest. If you do it in a "good" way then what I type next is 100% guaranteed. Have not gotten the results with neutral or evil dialogue choices.
She apologizes to you for making your love life hell, and as long as you forgive her, it continues. She actually might apologize twice if you have been very good. She was afraid of losing her freedom, until she became afraid of losing you. Once you complete her quest...
Spoiler rewarning
She will ask you to marry Her. The rest is up to you. You get two choices, and you can guess which one you need to choose to end up with her.