Firstly, to set the scene, I have only been on 2 dates with this man so I'm not invested in any thing yet and am early in the vetting process. I'm actively going on dates with other guys as well, keeping the roster full to avoid early attachment!

We're both 28, and I'm a fairly successful professional with a terminal degree & a 6 figure salary job. Not many people my age are at that level, so I've been choosing dates (OLD...I know its an iffy choice) based on education and their having what sounds like a steady job. I've obviously not given this guy any details about my salary, etc, but have been listening closely to information he discloses about his.

He has a college degree, but did not enjoy the field it was in, & so has recently transitioned to a new field (IT) where he is entry level and makes substantially less, at an hourly rate. He told me about this, and that he's in the national guard (American, btw) to supplement financially during this career transition. He also lives/is roommates with his little sister, who he seems close to. He's paid for our dates so far and made sure I didn't even get a chance to reach for the check. He just got a minor promotion, and does seem fairly driven/not intent on staying at a lower career level. He's friended me on social media and doesn't seem as of yet to be hiding any other red flags.

I don't plan to ever combine finances with a man again (I'm divorced), and don't want kids, so I don't particularly know if I should reject a guy who is otherwise my type and shows no other red flags yet simply because he isn't in my financial league. What are yalls thoughts on this?