Of course there's a possibility of it ending well.
You'll never know unless you pursue it and find out.
Then if things end, well, whatever - you're no worse off than you are right now, you're just back to being a free agent & on the market again. Big deal. If things go well, maybe you'll have a longer term relationship out of it than you seem to be assuming at the moment. Either way, it doesn't really look like you're in a losing position at all, as things will either be equal, or better. So, since you have nothing to lose.. take a shot and find out.
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No
for supporting trump. Because doing so is deplorable.