Tell-Tale First Date Questions

By Jeff Cohen, freelance writer (cohenwriting@aol.com)

It’s your first date and you really want to get to know the new person sitting across from you at the table. You want to ask all the right questions, but you don’t want it to seem like you’re interrogating them. How do you know what to ask them without getting too personal too soon? Asking these subtle questions and then really paying attention to the answers should help to clue you in a little better.

What are you really good at? This is a great question because you can steer it in any direction that you’d like. If you find out that he was the quarterback of his high school and college football teams, it’s safe to assume that this guy is into sports. If she tells you that she played the piano for ten years that can be your opening to ask her more about her favorite kind of music. With the basic interests revealed, you can be better prepared for the specific kinds of questions that you might want to ask next.

Where would you go on a dream vacation? By asking this question, you can easily find out if you’re dealing with an indoor or outdoor type of person. Someone who says they would love to go snorkeling off a boat might not be the same person who loves to tour the inside of museums. Ask what kinds of things they might do on their vacation and how they’d like to spend their time off. That should help to clue you in to how your date might like to spend their weekends and downtime in general.

What was your childhood like? Certain people define themselves through their childhood and how they grew up. If they identify with memories of always being out playing with their friends and siblings, they are probably quite the social butterfly. Any chance they had, they would be out exploring and making new friends. If they point to situations of solitude and being off doing their own thing, they may have tendencies to be a bit of a loner. That’s not necessarily a bad thing, but if you feel that it doesn’t really mesh with your outgoing personality, this would certainly be a good time to find that out.

What would you do with one million dollars? While this question might seem all too general, it can actually be quite telling. The way that a person responds to a question like this can say a lot about who they are and where their priorities rest. Does he choose to run out and buy a super flashy sports car or does he invest most of it in mutual funds to secure his future? Does she buy a fancy wardrobe or does she buy her mother that dream house? By asking this kind of question, you can clue yourself in to whether or not this person is focused solely on themselves or on sharing the wealth with those they care about.

Jeff Cohen is the author of the e-book, 30 Minute Guide to Online Dating. It's a must-read for anyone looking to master the art of online dating without wasting hours of valuable time. To learn more about the e-book and purchase a copy, please visit 30 Minute Guide to Online Dating.