Questions: Dating

There's this one lady I met recently. A nice tall Korean woman. Really chill; down-to-earth. She's just a friend, but I only just found out today she's a big-shot manager at a semiconductor company. She earns about $80K a year (115 million won annually). I was surprised, because I usually assume upper middle-class and rich people are complete snobs.

If she had no financial expectations from you and didn't care how much you made or what you did for a living, would you, as a guy, be fine dating a woman who earned at least twice as much money as you?

If he was a decent guy and had steady income and could take care of his own bills (even if he's poor), would you, as a girl, be fine dating a man who earned half as much money as you and was relatively poor?

I’ve liked this girl at my job since I’ve met her. I’ve done things that made it pretty obvious I was crushing on her, I would try to impress her with things, watch her favorite shows and talk about them with her at work, motivate her to pursue her dreams. I was really into her. She had a boyfriend though and eventually I felt it was pointless and I wanted to be respectful. So I tried to move on by dating other girls. They didn’t work out and my last girlfriend was very toxic. I tried burying my feelings for her through other relationships. After that I started thinking about her again, I wanted to tell her that I had liked her all along and everything but I would see her hang out with this guy from work all the time and everyone there basically thinks they are an item or will be. It’s crushing me thinking that he’s probably going to get her, she talks to him all the time. It used to be me. But that was when she had a boyfriend. I stopped talking to her when I dated those girls because I wanted to get over her. I’m not mad that she might be moving on to a different guy but I don’t know if I should try to tell her how I feel or if I should let my feelings go. The thing is she would never know how I felt about her. I just don’t want to make things awkward and I already have anxiety, if she rejects me I’ll probably feel so crushed to have to be around her again.

So I think we all know that it's not smart to call a beautiful girl, beautiful, as she already knows that and most likely hears that on a daily basis. Thus that compliment no longer holds any value, and you come across as an unoriginal.

But at what point does the prettiness of the girl surpass the threshold, in your opinion, of being "too" pretty to be called beautiful, to the point that the compliment still holds value?

Based on math, the uglier the girl, the more value that word holds, but as the prettiness goes up, you get diminishing returns per investment.

The math would dictate that 10 would be too pretty to use that word, but I think the actual threshold is subjective and would differ per person, because one might feel like "it's not worth it anymore after a certain point, because even though you get "some" return on investment, it's not a significant amount".