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Renegade Silver Meadow
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I recommend against repeated attempts at seduction. Henry has made his position clear, and he's not in a mood to be tempted. If you keep trying, you're showing disrespect for his feelings and boundaries.
He's a big old softie! He's only mean to you when he thinks you'll like it, or maybe when there's no other way to get through to you. You gotta show that you get the message. The date was supposed to be fun, but it's also a break from routine; a new venue might be a good opportunity to talk things over from a fresh perspective. If you can find a stretch of beach to walk along that's private enough, or a deserted corner near an ice cream stand, maybe try broaching some of the big topics.
The two big ones he just cited are 1) that he wants you to be happy, and he doesn't want to stand in the way of your happiness, and 2) he feels like he can't trust you. This is a thorny combo: if he feels like he can't trust you, then he won't trust that you're really satisfied when you say you are. You have to tell it to him in a way he'll believe, and that might be hard for you. You've been telling him that you're happy enough, and that you see it as a worthwhile compromise to forego some things that would be nice to have in your life to have him, but that hasn't worked; it's not what he's looking for. He's a softy, he's sensitive, and he loves you--he doesn't want you to have to compromise, and every time you tell him he's worth a few sacrifices is a reminder that because he's here with you, you're not the person you wish you were. Your psycopathy might make it difficult to understand, but Henry doesn't want to negotiate or make a deal with you--he wants desperately to be able to help you live the life you want to live, and he's frightened and hurt at the idea that he might not fit into that life.
You need to feel out new boundaries. Ask him how he feels about the situation, and just listen. Have you talked much about what your transition means for you(pl) as a couple? I get the sense that it's been happening mostly on your own initiative, and he's been on the outside looking in. Talk about your plans and wishes, and ask how he feels about them. Don't try to make offers to him right now, he's not looking for concessions; and don't try to discount his concerns, he wants to be heard and respected. And if you can think up any broad romantic gesture, doing something that will remind him of your first date, or when your proposal happened, or some event that made you two decide you were right for each other, lean into it. That's the sort of thing that will help him understand that you really do value your relationship, and want it to continue. Treating your relationship as an exercise in haggling will not speak to his romantic heart.
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