Apologizing in Advance Is the Nice Thing to Do
You know you’re speaking to a genuinely nice guy when he apologizes before asking a totally inappropriate question. What, she should be thankful that you decided to apologize before opening with an incredibly invasive question? What she should be thankful for is that you opened up with a red flag, so she knows to block your number from the get-go.

Most guys wouldn’t warn their chat partner that an inappropriate question was coming, but then again, most guys wouldn’t ask it in the first place. The more this guy opens his mouth, the less he has a chance of actually getting with anyone.