I am not one to give advice on this topic, but I think your own post gives you all the advice you need. It reads to me as an argument for just staying friends.
It would be easy if it just weren't so hard.
What makes it easy is that you already know the answer. Almost everything you wrote describes and argues for this answer.
What makes it hard is that you do not like this answer. All that you say against it is "don't wanna."
You are asking here in the hope of getting a different answer, in order to sustain the pretence that you do not know what you do know.
I do understand, in the remote part of my brain that processes things rationally
Making it remote is another way of maintaining the pretence. It is as remote or as near as you choose it to be.
To me your description sounds like on the one hand I would enjoy having a sexual relationship with you and on the other hand, he doesn't want to damage his relationship with your dad.
To what extent he would let desires overrule his principles of what he thinks respecting your dad is important to him, depends a lot on parts of his personality that you haven't written about.
I am 99% sure that if I were to lean against him or something while sitting beside him, he would physically draw away from me.
Having done a few calibration exercises, 99% is really a lot and unless you actually tried it, I would not expect it to be reasonable to assess that probability.
One rationality technique would be to actually attach probabilities to the various uncertainties that you have, and see whether you can test some of them without cost like what happens when you lean against him.
There seem to be basically two questions:
You probably want to answer those two separately.
Hello, LessWrong community. I have a question, my dears, for you. I hope it will not annoy anyone as it is admittedly a self-indulgent question which perhaps does not fit very well within the landscape of LessWrong content; however, I have inwardly justified posting it anyway because a) I genuinely need advice, and b) I trust LW more than I trust the entire rest of the internet to give me clear, honest, good advice. I know LW is not a relationship advice column, but I am quite new to rationality concepts and need some help applying them to a relationship dilemma in my real life that I can't tell anyone about in my personal life for reasons that I will clarify below. I would appreciate any thoughts this community is willing to offer about my situation, as I greatly value your honest insight.
Where to start.
I have this friend. Let's call him Hector. He's 23 years older than me (I'm 29F); in fact, he's an old friend of my dad's from way back.
Hector works out of state during the summer months, so he's only here half the year, and during the off-season he spends a lot of time at my dad's. Before, we would see each other whenever I came to visit my dad (daily - my dad and I are close) and we were always friendly, but over the past two years he and I have started to develop a much closer friendship. He was here for us when my dad had a stroke last winter, for example, and I started to feel myself gravitating toward him and missing him when he wasn't around. It wasn't really an intentional thing -- we just sort of bonded. It was very easy and natural.
I was recently forced by circumstance to move back in with my dad temporarily, which has only increased the amount of time I spend with Hector. He has interesting life stories and is funny, and he listens to me when I need someone to talk to about my current situation (I'm going through a divorce on stilted but mostly friendly terms with my somewhat cold and closed-off soon-to-be-ex husband). Sometimes Hector and I sit up and talk late into the night, losing track of time until we see the sun starting to come up. He makes me laugh a great deal. I feel good when I'm with him.
Mostly, my feelings toward him are healthy and reasonable. But I also feel somewhat romantically attracted to him. I fear this will eventually wreck everything.
I don't know if my romantic interest in Hector is reciprocated or not. He sometimes seems to regard me in a parental way, probably since he has grown kids around my age. On the other hand, he sometimes does things that in any other context between a man and a woman would probably be interpreted as sexual interest. He's very attentive to me and even protective over me, and seems to enjoy spending time together. I know he trusts me deeply, because he tells me things he doesn't share with anyone. We have so many inside jokes. On days when I am careful about my appearance, he always notices it and tells me how pretty I look. One evening, he was not feeling well so I asked if there's anything at all I can do to make him feel better, and he said "you're [my friend's] daughter, so goodnight."
Other times, though, he seems to be utterly uninterested in me sexually -- "closed" body language, shortness/irritation with me that can come off as borderline mean sometimes, and if he ever touches me, it's pretty much invariably an accident. I am 99% sure that if I were to lean against him or something while sitting beside him, he would physically draw away from me.
I don't want to have an official relationship with Hector or anything. That seems very complicated and awkward. Besides, I'm not stupid. My dad would hate it. Hector's kids and extended family would, I'm sure, hate it too. I don't think we are compatible as lovers, really at all. Certainly not enough to blow our lives up and not have it become a disaster unworthy of the mess it would make. I am not especially pleased about this, but I at least have to admit the truth of it. The consequences of ignoring the facts of the situation are too steep to roll the dice and see what happens. It affects too many other people, etc.
Furthermore, honestly Hector and I are in two different places ideologically. This is probably inevitable. He is 23 years older than I am, after all, and this reality acts as a constant invisible barrier between us. I'm even careful not to make too many claims on my friendship with him out loud, because I'm afraid doing so would only make our age difference seem suddenly more jarring and that he'd feel quietly weird about it, like it's wrong on some level to be close with someone so much younger and less experienced in life than he is. I'm afraid there's some part of him that feels he has no business bonding with me at all and that our friendship is completely inappropriate. It's just that bonding has been nice and effortless, whereas stopping it would be comparatively troublesome, especially now.
I would, however, be happy to have like a "friends with benefits" situation except that I'm afraid my feelings might get out of hand if we did that. Specifically, I fear my fondness for him would become too powerful an intoxicant in the context of a sexual relationship, and that I would end up wanting more out of him and getting hurt.
If I could guarantee that this would not happen, then our current close, happy friendship with sex added would make for the ideal dynamic between us as far as I'm concerned. He's really a strikingly attractive man, and I've been finding myself increasingly distracted by the sexual tension between us lately and even thinking about it when he's away. The trouble is that I would have to explain to him that I only want to sleep with him and stay friends and not be a couple. I'm not sure he would be receptive to the sex part, for many reasons. At any rate, I certainly don't think it would ever occur to him that I would be interested in a truly no-strings-attached sexual friendship without me telling him point-blank, which doesn't seem like such a wise idea.
I do understand, in the remote part of my brain that processes things rationally, that sexual desire is rather a mundane and unremarkable feeling to have toward another person, one that can absolutely exist without ever being gratified. I don't need to do anything about it; in fact, I think most people would tell me it's probably best if I just let this one go.
But the thing is that I really, really don't want to. It would be easy if it just weren't so hard. I mean, it's not every day that you effortlessly click with someone. I also can't just abandon our friendship without explaining why, as that's not correct social behavior and besides that I treasure my friendship with him. It means something to me. Furthermore, it's next to impossible to avoid Hector, even if I wanted to, since, as I've already explained before, he's a good friend of my dad's and is therefore around often.
What should I do? Are there any particular posts here on LessWrong that you can think of that would be useful here, any specific rationality concepts that would help me proceed wisely? General thoughts, commentary, and of course advice are also welcome, as again I can't talk about this with anyone in my life and I can't see past my feelings enough to figure out where I'm supposed to go from here.
TIA, frieeeeends!