No thanks on the truck! Got my Turtle (Green CRV) and he's good.

Did you sign any agreements with the company you're a contractor with now that would preclude you from working under your own company name now? And what if things with that company get better, and you decide to stay with them? Any chance of that happening?

As for the dating thing, I think it's fine to meet guy #2, just if he asks "are you seeing anyone," answer honestly. What you've told us is enough info to share.