If being loose with money is a large red flag, than the situation above is a large green flag. And do you know how rare it is for women to pay for a first date...
According to chat GPT, there is a 4051 year gap between Morgoth's death and Bilbo's birthday. By the ending years in the battle of Morgoth, most of the evil elves were dead or repentant. I think you can take the moral high ground if you are well past 4000 years since your people did foolish evil things. EDIT: I guess the it's not just the Simirils and the One Ring. But the Arkenstone was magic jewelry people fought and died over. I guess Tolkien had a favorite kind of story...and that's okay.