Search Results: dating much older guy

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?

Met this guy on New Years. Didn’t hangout until the 6th. He took me to a trendy bar our first date. No food, just drinks. This was at 7:30p. Go back to his place and end up hooking up. I know the rules of dating. No hooking up too soon. Well, I did. He was hot and figured if it was a one-nighter, it wouldn’t be a big deal, as he was pretty attractive. Well, since the 6th we’ve hung out 5x. He sees me once a week. We only text when we’re arranging a time to meet and hang. No corresponding in between. I get it. Some people don’t text much. But he’s a millennial. Plus, it’s my understanding that when a guy is into you, he’s going to try and see you more than once a week, or at least text here and there to stoke the flames if he is truly that busy. He hasn’t taken me out on another date since the first time. Last time we hung, he said he wanted to take me to sushi bc I told him it was my favorite. I don’t wanna screw up and miss the red flags here. Im thinking of breaking things off next time we hang. We were suppose to hang Monday, but he cancelled and rescheduled for the following Sunday. Guess I want confrontation if this is the right move to make. I’m use to just “going with the flow” and it doesn’t workout too well for me. I don’t wanna be a booty call, but I probably did that to myself by sleeping with him too soon, but what’s done is done. I don’t text him bc I’m trying to respect him and not come off as some crazy clingy. I’ve attempted texting with a silly meme. He responded quickly, but didn’t continue the conversation. I’m just not use to dating guys my age. Usually way older. So I’m new but wise enough to understand when something is “off”. Is he just busy? Or have a fallen into the “booty call” category for him?