Search Results: dating an older woman

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?

A long while back, my brother went out on a date. She was only 2 years older and had her wedding ring. When he asked her about it, she was straight forward that yes she's married for 5 years but they date others for fun.

She then suggested to come over while her husband is present. My brother initially thought she was lying until she called her husband. The guy explained to him that he already knew about the date, is welcome to come and they're been in an open marriage for since their 2nd year. Needless to say my brother found it weird and walked away afterwards.

Would you feel comfortable dating an older woman? What would lead you to doing so? Do you find older women attractive?