Search Results: wanting to sleep with someone

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?

August 2020, me and my best friend admitted to liking each other. He told me he loves me and wants a relationship with me. I explained that can never happen 1) it’ll ruin our friendship 2) I’m meant to be a lesbian.

We’ve slept together a couple of times since admitting it, I was fighting the feelings but I ended up giving in. We haven’t slept together since November, now I can’t stop thinking about him; It’s constant.

I’ve told him I want him but I’m scared of unintentionally hurting him. What happens if we’re together and a girl comes along and steals my heart? I’ll definitely lose my best friend.
I’ve never cheated before but because I’ve never properly dated a man, I have that worry. I just don’t know what to do.

So many people have said ‘you can do so much better than him’. It’s not about looks and I know and understand him. I like his personality more.

Before someone states: ‘you’re obviously bisexual’. The truth is, I don’t know what I am anymore. I’m leaning towards homoflexible, however I’m just not having a label anymore.

Do me and him chance it and give it a go or do we just stay friends and ignore the feelings?