"Hey, how about for our first date, we grab a bite to eat, and then I [vague reference to oral here]." Chances are slim you are going to be like, "Yeah, dude. There's no shame in being unemployed for a stretch or getting paid under the counter. Either he's seeing someone else and doesn't want to be spotted out with another woman in his hometown, he doesn't see a future with you and doesn't want you knowing where he lives just so he can keep his distance, or he's basically a hoarder and he doesn't want you to see the state his place is in.
Let's go grab some Frostys and then bang." Socially competent people know to just ask someone out to dinner and then let the banging happen organically. But if he's describing himself as an "entrepreneur" and refuses to get more detailed or refers to his job situation as "complicated" instead of being up front, that should be a red flag. It's one thing if he's being a gentleman and doesn't want you to make a long drive out to see him.
I got the sense that he was trying to instigate some sort of catfight to feed his ego, and I wasn’t going to play into it, so I changed the subject.
"Because it was still fairly early, we decided to visit his neighborhood bar.
After 15 minutes of being ignored, I decided to leave.