When you're on a first date you want to seem relaxed, slightly offhand (not too much of course) and most of all, charming. But how do you ask questions without "prying"? It's almost always hard to find a balance but the following should help if you want to find out:
- His age. For some people this is a sensitive issue. During a date however, it wouldn't be as offensive because both parties would most likely want to know each others' age anyway. You can probably tell how old he is from his physical appearance, but sometimes it's trickier than that. Try not to pointedly ask up front - "How old are you?" Instead, bring up when you were in high school (or college), then ask something like "So when did you graduate?" Then figure it out. If you prefer being straightforward, ask him "When were you born?"
- His job. Most people expect to be asked about their work during a first date. It's only normal for a person to want to find out more about what the other is doing. Don't feel shy about asking him what he does for a living. Just say "What do you do for a living?" or "Where do you work?" and go from there.
- His family. Some people prefer to keep family-related topics to themselves on a first date. If you're truly a family-person you may want to find out more about his as well. Whatever you do, don't bring up the parents before he does. Instead, ask if he has any brothers or sisters. If he seems comfortable talking about them he might just bring up his parents as well. That way you can get an idea about his relationship with his family.
- His favorite... It's always nice to have a conversation about your favorite things, pastimes, attractions... Anything! If you like baseball, ask him if he likes the sport too. It doesn't matter if his answer is a no because you're bound to find out what he really likes. Tell him about your backpacking experience in Europe and ask him if he has traveled before. Or ask him what he would do if he were given a week off. Through these questions you will know more about his favorite things, and how he spends most of his leisure time.
- His college background. Some questions may seem confrontational when you least expect them to be. If a man has never been to college he may find it slightly offensive if you ask him "Did you graduate from college?" Use subtlety by asking "Which college did you graduate from?" If he's a successful working man he should be comfortable correcting you.
- His marital status. This is a tricky question. Depending on your date, it may not even be necessary. But if you have reason to believe that he may have been married before just ask him - "You said (so and so). Am I right to assume that you've been married before?" If he is currently married, and out on a date with you, you may not be able to count on a "right answer" if you ask about his marital status.
- His relationship background. Both men and women tend to be curious about their dates' previous relationships. It's not advisable to discuss these during a first date, but most of us just can't resist. Try waiting until your second or third date to ask questions about the exes. Some people go through an entire relationship without knowing about each other's pasts. Others are more comfortable sharing this information. Figure out which one your date is before asking anything. If he brings up an ex girlfriend without you asking, he may still be emotionally attached to her. But if you ask something like "So how many relationships have you had?" he may give you a straight answer that will lead you to understand his dating patterns more.
- His religion. No one ever recommends bringing up religion in any conversation, but if this is truly important to you, you should feel comfortable asking (and you should certainly be prepared for an answer regardless). For some people, religion is nonnegotiable. If you're one of these people, throw in the question amidst a conversation about what you do during the weekends. Perhaps you could say "I go to the church every Sunday. Do you believe in religion?" His reaction to that should give you an answer. Don't ask "Are you Christian (or any other denomination)?" up front. It's just not tasteful.
- Don't put too much pressure on him with questions. It makes you seem impersonal, and puts him in a spot. We all know how badly people can perform under pressure. By interrogating him you defeat the purpose of the first date.
- Build rapport with your date by listening when he speaks and you'll find out a lot more than by just asking questions.
- Whatever you do, do not bring a hard copy "list of questions." Be casual. Have fun.
- If you feel that a question is really important and you have to know the answer, go ahead and instinctively ask him. It shouldn't hurt your future if you were both getting along well to begin with.