Yeah, it was a bit tough to touch on all the subjects I wanted to mention and there was no way I could really be deep with any of them because of the length and readability reasons. I am not a writer.
Sounds like it's time to hire someone to ghost write your memoir. Or not. :)
Sounds like you've found your way into a role that could best be called "sugar daddy" or close to it. Not pejoratives here, just condensing a few paragraphs into a term that's borderline cliche, but I guess it exists for a reason. If I understand it right, there's a personal connection, but there's also a financial imbalance strong enough it does intrude on the relationship in some ways, even if it's on the whole mutually beneficial. You're in a position to be able to provide some now and then and can enjoy it, and they're in a place where they really appreciate it, but it's also not the core of your relationship, just one of the fringe criteria.
I could almost certainly get a legally binding contract written up to protect my assets I suppose. Hell, I'd be fine even if I lost a bunch in a lawsuit. I just don't want the hassle, the risk, or having that much baggage when the inevitable breakup occurs. ... Then, we have the really awkward situation of proposing that contract or a prenuptial agreement. While they're more acceptable today they are basically saying that I don't believe the relationship will last and that I think they're a money grubbing whore. I'm not really sure how to put that in a light manner that will be honest. It's not like I can say that I'm interested in protecting them...
I'm going to disagree a little here. I have to ask, when you get car insurance, do you say, "It's because I'm planning to crash the car?" Do you have insurance on your house because it's preparation for burning it to the ground? Does health insurance mean you're trying to catch cancer? I know that a prenup, being about a relationship instead of physical stuff feels a little different and I can see that, but I think that's overly negative. You could also just look at it as a contingency plan. Contingency plans are great for *everything*. I have a contingency plan for supper, for what happens if my Friday night falls through, and what happens if my wife dies and leaves me with two little kids, or one, or none. I don't want any of these things to happen, but I've thought about all of them, to at least some extent.
It seems clear that money is already intruding upon your relationships. If it wasn't at all, I'd say that's great and drop it. But since it is, a prenup is just one of many ways to manage how and to what extent it intrudes. Acknowledging that fact doesn't necessarily turn into an insult to your partner, at least in my mind. For one semi-random data point, the financial guy Dave Ramsey, who leans pretty conservative Christian and holds the belief "when you get married, two become one in all ways" still recommends prenups when more than a million dollars is involved.
On the flip side, if past history indicates you're not entirely comfortable in strictly monogamous relationships, that's completely outside the financial discussion. I think that can be addressed, too, if you want it to be, but through mostly different means.
I am certainly open to advice or insight if you have any.
Well, I'm just some random schlub on the internet, so I'm not sure what my advice is worth. I haven't been in your situation, and the closest thing to a credential I have is "I like to think about stuff"and sometimes listen to other people's situations. Mostly I guess it depends how much you're bothered by things. If you're in a good place and were just commenting, maybe there's nothing to be done. But if it weighs on you, there's probably room for change, if you want to go for it. How's that for some ultimately weak commentary?