What I meant: if you wish to know about a man, get him talking about something he enjoys or at which he has been successful; that will usually loosen his tongue on other subjects. If you ask him about his job and he says he has a business, ask him about his business; he will eventually tell you if it has been successful or not. Most men do not immediately start telling you everything about themselves; both men and woman are usually cautious and polite, but a woman can ask questions. If you hit upon a subject he likes, he will eventually tell you everything you want to know!
Most men are cautious about money and finances; focusing on getting to know a woman as a person is more proper. The early mention of money in many cultures is considered impolite, unless the father is demanding far too many goats for his daughter! Good for women to know what is polite and acceptable in his culture. Not a criticism, but Slavic women, by nature, seem more direct with questions; if they want to know something, they ask. What is more simple than that!? Typically, Americans tend to be more subtle in their communication; it is just part of our way. If you are having your first dance, sometimes best to let the man lead. (If he cannot dance, then you show him how!)
Sometimes cultural differences are funny. A Russian friend at work once said he wanted to introduce me to his single daughter, because "she would like to meet a man that owned a Corvette!" (Corvette is an American sports car.) He showed me a picture of her beautiful younger sister and wanted to know when I could stop by his house? Pavel was a kind and sweet guy and meant nothing bad; I understood him and we had a good ...but, he was serious. Men will be kind and patient if they like you. Most Americans would meet the girl and offer her a ride in the Corvette! If a man is on this site, he knows a little about Slavic culture; however, keep in mind, some men have no class within their own society! or anywhere else in the world, for that matter. That will not be any different here!
Regarding directness; not long ago, a young woman contacted me saying she was interested in a serious relationship and did not want to waste any time. She also said if I was interested in her, please send flowers or chocolates to prove my sincerity. I smiled inside and not quickly offended; but within the next ten days I had been reminded several times. Within the first two weeks, she wanted to know what was taking me so long; I was not moving quickly enough! I actually planned to send something in the mail, but...in the US, this is much too direct. Regardless of how pretty, most men here would ignore her without further notice; requiring (demanding) gifts on the first date is bad sign and possible warning of things to come...better to err on the side of caution.
Ultimately, you must decide, Nat. If you get him talking, you may learn a lot about him. Bragging a little about his success is not the kiss of death; many generous and well-intentioned men are somewhat clueless about manners and how to talk to women. Does not mean you cannot train him! (If he is selfish, he cannot be trained!) There are also men who need to display their wealth; for them, a sign of power and success. To me, this is psychological overcompensation for other deficiencies. For instance, if I had houses, a boat, plane, money, an island, etc., I would never reveal it on a dating site, for I would always question why women were interested in me...
Do not know if this helps, but these are just some thoughts from my experiences.