It’s OK to ask personal questions on a first date.

Personal is not the same thing as private.

This is not just semantics; they are two different types of questions.  A private question addresses matters which are private. A personal question elicits an answer that is unique to that person.

Asking questions that pry into private matters – on a first date is just too soon.  Topics that are too private to ask on a first (or second) date are social security numbers, medical conditions, past relationships, money, and complicated family issues. If you know of something that is a sensitive topic to your date, then don’t ask it on a first date. No matter how curious you are. It’s just too soon.

Personal questions are those that open the door to talk about what feels important or interesting to them – to the unique person that they are.  The answers are personal; they are different from person to person.  It’s questions like these that start great conversations where you can really get to know each other. These can really jumpstart a relationship.

Responding with kindness

Before we examine some examples of a “personal” question, let us consider for a moment how we should best respond to the answers we are likely to receive to such questions. Now that you have asked a question about the other’s thoughts or feelings, and the person has responded in that manner, it is important that you ensure that your date feels good about having done so. 

You do this by making appreciative comments. For example, “Wow, that was an amazing story. Thanks for sharing that.” You can also react positively by affirming or validating what you just heard. For example, “That was some experience. You sure had nerve!” 

You have asked questions that encouraged your date to speak openly. Now, ensure that they are glad they did, through the manner in which you receive that openness. Show that you are receptive, by letting them know that you found what they shared interesting or informative, funny or inspiring. 

Responding in kind

But that is not all. It is also important to return the favor. It is appropriate and helpful to match your date by being similarly open about yourself – of course, as suited to the stage in the dating process. This means offering to share similar things about yourself, depending on whatever makes sense in the context.

For example, if the person you are dating has just told you about how excited she was the first time she flew on a plane, it would ideally be good for you to share something similar about yourself. Or, for example, if the person you are dating shares with you a difficult bullying experience as a child, it would be great if you could share something of your own about growing up.

Obviously, the point isn’t to mirror the other person exactly. The idea is to match the person – if appropriate – in the kind of information you exchange. When you share insights and stories about yourself, it makes it a lot easier for this process of sharing to continue in a positive direction.

What does a personal question look like?

In addition to asking, “What do you do?” and leading into “so what does a [teacher/ lawyer/ entrepreneur] do?”, ask “That’s so interesting, how’d you get into that?”  You are opening the conversation to talk about themselves.

Not just “How was your weekend?”; also ask, “What was the best part of your weekend?”

Other more personal questions you might ask:

“How did that make you feel?” 

“What do you consider your biggest accomplishment and why?”

“What is a great gift you once received?”

“How’d you meet your best friend?”

“Aside from the job you have now, what sort of work would you like to do?”

“What is something that you know a lot about?”

“What is your favorite little-known place in this city?”

In conclusion

Not everyone finds it easy to ask and answer questions. This can be especially difficult if someone is new to dating, and is not comfortable interacting in this way with someone of the opposite gender. This can result in the conversation staying on a very basic level, which is unhelpful when the goal is to open up a meaningful conversation.

That is why it is important that you put some thought into the kinds of questions and answers you would like to use during the conversation. Don’t be afraid to write a list of great “personal” questions and make an effort to prepare yourself to give fulfilling answers to such questions put to you. You will both have a much more enjoyable and productive conversation.

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