"fb2- I guess the red flags for me personally was that he was cheap, he didn't bother to dress nice to meet me for the first time, and his political beliefs were opposite mine..."
Ya, understandable, dress could be a turn off. I for example like very clean and simply dressed and intelligent women with shoulder length hair preferably tied up in a pony tail. And loud colors, perfume, high heals and a lot of makeup and hair styling would definitely be a red flag for me!
On the other hand perhaps he was just being himself ("Country Boy") to set you at ease. Puzzling that he only dates teachers yet complains about their work ethic. My theory is that his kids get a lot of homework, have trouble with Math, he cannot afford expensive day camps in Summer and the teacher is not available to talk to about all this.
I'd go with Kerry's pen pal approach for now. This might serve to filter out the red flag types before you waste your time meeting them in person. And then when you meet them you can judge if what you see is what you expected. You also need more time to heal from the trauma of infidelity. Just my idiotic ideas.
