Its called a “fling” for a reason and you caught feelings?

I wonder why, you really sound lovely and not judgy at all

You sound like you are making up a list of reasons on how you’re too good for him and that he should have felt lucky you let him enter you. Good for you and your generational wealth. He wasn’t interested.

Your boasting about your material wealth exposes your poverty in human qualities. Why did you call him a "local waiter" if he collects unemployment? For low-skilled work, if you're not currently doing it, you don't get to keep the title, you're just a bum.

And what did you learn from this fling? A fling is wonderful, but learn something. I got dumped by a fling a month ago (she was quite the opposite of the fling described; she was smart, ambitious, easy to talk to, and she was drop dead gorgeous) but I learned what I wanted and what I didn’t. Now I’m seeing someone who’s even more amazing because I learned what I’m worth. Do the same.

Gee I can't imagine why.

Why are you surprised. You basically just described a stupid person yet you are surprised when he does stupid things... But you are the real idiot for dating him so it all falls on you lol

So, first of all, you yourself called it a fling, and second of all, you chose him to have said fling with.Third of all, congratulations on all your achievements, but it isn’t really relevant or related to why you choose to date someone. If you have high material standards in dating, then maybe you should find a partner that matches instead of coming off like you want to put yourself above him. To put things in perspective—-I’m about to graduate grad school with my MBA, hold 5 certifications, and just got a 90 K job offer with a top company not even out of grad yet. My partner is different than I achievement wise, but does it really matter to me, or in the grand scheme of things? He’s 3 years older yet has a flexible / lax work schedule, makes almost 30 K less, and will likely never go back to school, but you know what? He’s a quality individual with the biggest, most forgiving heart I know, loyal, and would do anything for family & friends. We’re almost at 2 years. Would I have anything different? No. 🤷‍♀️

You dodged one hell of a bullet. Someone like that would go through all your money easily.

Recognize your self worth