Search Results: has he lost interest

I love what I do, I do what I want. I've been a landlord since I was 25, and an investor. I volunteer for non-profits instead of working a 9-5. Periodically, I take low paying jobs for fun like being an assistant teacher. Sometimes I'm in college classes. Or, I just spend the year hanging out with family or traveling. It's an out-of-the-box lifestyle. I can sleep in, go to bed late. I'm free.

The problem is dating.

If I say I'm a 33 yr old student, people want to know what I'm going to do with the degree. Nothing. I don't need it. I just like to learn. They want to know what I have planned for a "career". Nothing, I enjoy making money while just relaxing and enjoying life. I went out of my way to figure out how to earn money while working the least amount I could in a formal job.

If I say assistant teacher, they think "that's cute" and ask when I plan to be an actual teacher or move to the next "bigger" job.

If I say landlord or investor, people react like they see dollar signs or get intimidated. They start trying to figure out how rich I am, how I got to where I am, and then they exit when they feel too far behind is the impression I get. Or, they immediately stop being interested romantically and want me to "hook them up".

The most people, men and women, run away when I mention being an investor or landlord. People think student or assistant teacher is cute and will actually date me. Volunteer brings people back to, "But how do you make money?"

Personally, I'm old fashioned. I feel the focus should be on how much money the man brings in. I'm surprised how much focus is placed on me. I know a lot of successful guys who would date a girl working a low paying job or no job at all. So, why is it even really an issue if I make a lot? It's an issue if I don't make much, but it's not nearly as much of an issue as me possibly making more.

Has anyone else had these issues with dating? Have you lost interest in someone because of their job, how much they make, etc?

I've been talking to this guy for less than a month.. in the beginning he was somewhat pushy to meet me. We tried meeting but something got in the way of not meeting up. He has told me things like:
He says he really likes me
Compliments me a lot
Tells me he wants me/earning for me
Tells me he really wants to meet me and says he can but can't wait to meet me.
He says that he doesn't wanna lose me /the potential of meeting me, meaning if we haven't met for a few months that he's worried he will lose interest.
He has told his friend about me.
All he wants is to meet up and see how things go. He usually prefers meeting up right away.
He genuinely asked me questions and seems like a down to earth guy.
he's still very goofy and laughing with me but i find the more we talk he seems very calm. he's very honest with me and seems to communicate well. Things do get sexual and he has said he wants to have sex with me but he also wants all the other things that come with a relationship. Cuddling etc.
He asks me genuine questions about myself and what I've been up too during the day