Make Conversation Easy with These Questions

Have you considered how much easier conversation is when you skip the boring, basic get-to-know-you questions? We often feel obligated to ask about a person’s work, family life, and personal history because it is what we have been conditioned to do. After you have answered these questions a few dozen times through countless matches, it gets annoying and boring. Consider breaking the mold by asking these five easy, engaging questions that are sure to help you learn more about a match and keep the conversation flowing and anything but boring.

1. If You Could Have Three Wishes, What Would They Be and Why?

Hypothetical questions are designed to help you look deeper into a person’s psyche. Questions like this are an opportunity for you to learn what is important to another person. Do they have superficial wishes, or are there serious things that they want to change in their lives or the lives of others? Are they a bleeding heart for all the world’s problems or more focused on their lives? This question lets you answer those questions about their personality.

2. Do You Ever Look through People’s Cupboards?

Several months ago, the man I was dating left me alone in his home. About 20 minutes after he left, he called me, and I answered the phone. “I’m not done looking through your stuff yet; you can’t be bothering me!” Of course, I was joking. However, there are a lot of nosey people out there who do not hesitate to look through the cupboards of a stranger. It is a natural curiosity to want to know what people keep stored away. The question is whether or not you can handle being in a relationship with someone who does.

3. What Is Your Most Prized Possession and Why?

The item that we see as most prized is usually something priceless to us. An ornament from a special occasion. A family heirloom that we have always adored. This question gives you a piece of information about your match that you might not have found out until much later in a relationship. Not only will you learn about this one item that is important to them, but you will also get to hear the story behind it. Telling our own stories is the easiest form of communication.

4. Is Your Work Fulfilling?

There are people who really enjoy their jobs, and then there are those who simply do it to pay the bills – which one are you? Better yet, which one of these people is your online match? I find it hard to be with someone who does not find fulfillment in the work that they do because it often leads to them being upset or agitated with it on a regular basis. People who do find their work fulfilling will want to tell you the story of how their work came to be and why they love it. These stories can keep a conversation moving into other topics as both of you share your related histories.

5. If I Were to Run an Internet Search on You, What Would I Find?

Most people that you know are not “Googlable.” As in, if you were to search them you would find a social media profile, maybe an old news clipping, and a passing mention somewhere. Despite this, searching for someone has become the first step in getting to know more about them. What kind of information is out there about you? This question is an interesting way to talk about your achievements and your past that are alive and well on the World Wide Web.