You have planned everything down to the goodbye kiss. You have scripted everything about how the first date should go, when you will pick her up if you are a man, and what you will be wearing if you are a woman. You are now prepared for any eventuality. The date is going well but then something inside you blurts out a question that could have you both scrambling for cover. It seems that everyone who goes on a first date wants to know answers to many of the same questions, and quite often these questions are asked. The method of delivery however is another story as how you ascertain the answers can make the difference between a pleasant evening and a fork in the eye!

Its important to keep conversation and questions on a first date light and easy, there is nothing worse than someone giving you the third degree about everything under the sun. You are trying to get to know someone so don’t make him or her feel like they are filling out a mortgage application. Phrase your questions that will lead to the answers you seek, but without directly challenging the other person to give a quick and definitive response. So, lets look at some of the ways we can ask first date questions without making it seem like an interview.

In addition to chemistry, dating is really about strategy. Each person is attempting to determine various things about the other; some people are just more obvious than others.
But if you want to ask certain questions here are some clever ways to ask those first date question.

Sarcasm, this has always been a fairly useful tool in the questioning process. Sarcastic humor such as “I work 40 hours to be this poor” is a great way to open a conversation about finance, wealth and employment.

Humor will always be the greatest of all icebreakers, especially for difficult topics, and when used to elicit a response it can tell a person a great deal. Get into a conversation about movies and then mention a funny movie that has religious aspects to it. Now you have a method to move into a light discussion that can help you determine if your date is a religious person or not.

Semi-Direct questions should be tempered with smiles and lots of wine. If you want to know about the stability of a person and their career direction then phrase the question as a direct one but without asking it exactly that way. “If you could choose your dream job, what would it be?” Again, this opens the door to expand the conversation in direction that will give you some answers.

There are two other clever ways to ask questions on a first date but the person asking has to be a quick thinker and possess the ability to change direction quickly. They are Self-deprecating humor and confrontational. “I’m in shape. Round is a shape, right? This is a great example of self-deprecating humor and can be useful in a conversation about whether or not you eat healthy or go to a gym. For the confrontational approach, let us remember we are on a date so confrontational does not mean aggressive, it may just take the form of a contra point of view, “I can’t believe you would actually pick this movie over that one!”

When it comes to emotions you need to tread lightly, but it is important to ask certain questions when you are trying to determine the emotional baggage a person may be carrying around. Compassionate questioning works well if you already know of some break-up or issue in their lives that gives you concerns about the long-term potential of this person. “I heard about what you had gone through, I recently went through something similar” and then let the process continue from there. This is a type of question where you may need to back it off a bit if you see too emotional of a response, but its also perfect in that it give a good indication of their redness to move on.

All these possibilities are merely what I like to call probing hints.  They open a line of conversation without making you seem like an idiot or trying to stick your nose where it may not belong. The best first date questions never actually seem like questions, they are more like subtle nudges, directing people to those answers you’d like to have.

Of course, some people have no filter and may blurt out the most offensive questions. This is Volume questioning in which they will ask very blunt and often insulting questions to many people on many dates in hopes that somewhere along the line they get an affirmative response. This is quite often used by men when trying to determine if first date sex is a possibility before continuing. A good example of this might be “are you going to sleep with me, or do you want to split the bill?” Have fun and date safely!