I feel lonely, again, and I want to try dating and making new friends, but I dread the most common question, "so what do you do?"

I don't work. I was fired from my last job and had an ugly falling out with my boss that made matters even worse. That blew back my confidence and desire to get a new job a TON. I'm living with my mom and sister, and none of us work, but we live off a good amount of inheritance money from our grandparents who both passed on recently. Of course, it won't last, and my mom and I are trying to get our own businesses started so that we can create our own incomes and not depend on bosses and fixed hourly wages. I figure this privileged window of time is the perfect time to take a chance. The only problem is, I'm passionate about multiple things: art, music, cooking, gardening, and have a hard time nailing down a business or way to make money that will work for me.

If you're judging me harshly for what I just wrote above, then that's EXACTLY why I feel like I can't meet anybody new, because they'll hate me as soon as I am forced to admit that I'm unemployed and not making any money. I can phrase it in a way that sounds positive and nice, but they'll see right through it.

I don't know if ANY guy on earth would want to date me at this point in my life. It sucks that you can't find unconditional love, but I really doubt a guy would be attracted to me if I don't have a "real job", don't work for a living, and I fear putting myself out there and getting rejected on this basis. I've ALREADY been rejected multiple times, from various people, including "friends", bosses, men, etc, and it has been DEVASTATING to my self worth every single time. I can't take the pain of it.

I used to be insecure about my looks, but I'm over that now. I'm insecure about my unattractive life situation now.

Should I, once again, push down my deep feelings of loneliness and focus ONLY on getting some income going before I ever venture out of the house again, and meet new people? It was painful just answering the hair stylist's question about what I do for a living. Maybe it was just in my head, but I could tell she was judging me. She works. She has to work. I don't.