Ask questions about your date's family. Ask where she grew up and if she has any siblings. Ask her what her parents do for a living. Ask what she does for holidays or if she has any pets.
Job and Career
Ask your date what he does for a living and if he attended college. Ask him intriguing questions about his profession. For instance, if your date is an accountant, ask him what is the most rewarding part of helping people with monetary problems.
Everyone has some sort of talent, so ask your date about his. You may find out some quirky, yet interesting information about him. You may also get some laughs out of this, which is never bad while on a date.
Interests and Goals
Ask your date about her interests. Ask her what she likes to do in her spare time and if she has any hobbies. While you may not like all of her interests, you may find a few that you have in common. Once you find some common interests, talk more about them. Also ask your date about her goals in life. Ask her where she would like to be in a few years.
Another important question that you can ask your date is whether she is looking for a long-term relationship or simply wants friends. If your date just came out of an long relationship, she may not be looking to date immediately.