Search Results: how far would you go for love

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’m 32 he’s 20. I had met him because he is a family member of someone I was dating 3 years ago and we just clicked immediately. About a year ago he had to leave his moms house and I let him come stay with me over the course of this time he developed a drug addiction which ended up with me taking care of him. We sleep in the same bed together and are very close as far as friendship goes. I never thought of him in a romantic way because of our age difference but while he was away at rehab I realized I have more then just friendship feelings for him. We have both dated other people over the course of this past year and are open with each other about everything. We tell each other we love each other and he has told me (while sober) that he loves me more then any other female but has never shown me he wants a relationship with me. I want to tell him my feelings for him but I’m scared it will ruin the friendship that we have if he doesn’t feel the same.