We all want to be polite and patient on first dates—nobody wants to come off as pushy—but there are some instances when you should push your date to answer a question. And if he can’t or won’t, something is up. Ideally, your date is so comfortable with his past and himself that he’ll tell you just about anything! But, that’s rare and hard to come by. That being said, even the shyest or most private men owe you some basic information. The only reason they wouldn’t tell you these things is if it would shine an unflattering and probably accurate light on them. Here is information your date should be willing to divulge.
Whether or not he’s been married
If he wants a relationship or just a hookup
There are subtle ways to ask this, but he should be able to answer you. Men who won’t answer this are usually just looking for a hookup, but they don’t want to tell you because they were hoping to trick you into thinking they wanted something more.
Whether or not he has children
Also public record. Also something he should be willing to tell you. Did he think you wouldn’t find out eventually? Plus, you want to be with a man who is proud of his kids!
If he’s clean… (when you get there)
If sex is on the table, you definitely have the right to ask if he’s good. Heck, you have the right to see the records. Yes, even if you’re going to use condoms. Condoms don’t stop everything.
What he does for a living
If he won’t tell you what he does for a living, it’s either because he A) Doesn’t do anything B) Does something strange and/or illegal or C) Doesn’t want you to know he has a lot of money.
Why his last relationship ended
He doesn’t have to get into too much detail, but if he gets angry or irritated at the question then that relationship must have ended in an ugly way—and he may have been responsible. Either that or he’s still into the ex.