It sounds like you put yourself out there a couple of times and that takes guts. Truth is, we never really know how a risk is going to go, but if we never take risks, then we don’t progress very far either. From your verbiage it seems like you have low self confidence/worth. Give yourself some credit. Take some time to write down some things about yourself that are pretty cool. You’re a parent and sounds like you care about your kid, you care enough about yourself to ask for other support, you can cook and play chess, you have a job. These are not all givens. You own those things and I’m betting much more too.
As far as the romance situation, just from my own experience, I found myself asking out women that were “convenient.” Coworkers, people from high school, etc. Once I focused more on myself and stopped caring as much for a relationship did I ironically find more options. If you get involved in things you enjoy, there will be a much greater chance of finding someone that you click with. Join a chess club, do a yoga session at a fitness place, or even try something you’ve never done before. Try a cheap introductory dance lesson.
Just my opinions, take with a grain of salt. Best of luck with everything.
Did you say… an orange and black box?