How do you get the option to choose the greyed out dialogue options? Like the one after Riley does her helicopter thing?
It depends on your previous answers/play style. Try play a bit more aggressive (dialogues/choices) the story prior to that moment.
You need to agree with her on the cookie mint thing, that it tastes bad, and then be more dominant with her, enough that you can actually do her in the first meeting. From then on be more dominant with your choices with other women.
