If you dread the awkwardness of meeting someone new, you are not alone. It is unbelievably difficult to uphold a conversation with a complete stranger if you aren’t immediately on the same page. I mean, how is one to figure out that I am a misunderstood Krameresque figure if I don’t have the opportunity to tell them?

When faced with the butterflies of new social interactions, some people just wing it while others develop a standard tactic. In my more optimistic years, I believed if two people were meant to hit it off, they would. 

However, the moons have weathered me. I now acknowledge that, although there are some people with whom conversation will immediately flow easily, this is not the case for every instance. 

For this reason, I have formulated my very own set of 12 questions for new people I meet. You may ask, “Lisa, why are you interrogating your potential suitors?” To which I implore you not to knock it until you have tried it. 

If you opened this column thinking I would share my list of 12 questions with you, dear reader, I sincerely apologize. This list is very personalized to my specific quirks — and, frankly, I will be gatekeeping it in order to preserve its originality.

Not all hope is lost, though. If you would like to develop your very own list of questions, as a seasoned interrogator, I will offer you my sage wisdom.

BuzzFeed quiz questions

Yes, this sounds corny, but having a couple of lighthearted questions at the beginning of your list eases your interviewee into the incoming process. These questions can range from the person’s interests to their favorite foods. 

On my list, these are the questions that assuage the individual of their fears of being interrogated. While 12 questions may be an intimidating number, half of them are entirely for fun. Try to give these a tinge of subliminal meaning, because you really can’t go wrong being a nosy little minx.

Mini job interview

The questions in the middle of your list should be ones that prove the individual is qualified to occupy a place in your life. It is a coveted spot, and you should treat it as such. The meaty questions should measure an individual’s ability to stand up to difficult situations, perform well under pressure and not say anything too off-putting or terrifying.

Some of these may seem weird to ask a random person at a bar, but I have done it, and let me assure you — people love an opportunity to talk about themselves.

The hard hitters

The final category of questions are ones that inform you of an individual’s lifestyle, morals, character, values and personal history. 

If you were using these questions on a potential suitor, these inquiries are rather important. I would refrain from asking direct questions regarding their dating goals or marriage and children, but try to learn about how they pass each day. 

These questions can be lighthearted, but they should uncover things that you would like to know about the individual you are interrogating. The goal of this portion of your interrogation is to make the individual feel as though they are not being questioned, but rather as though they are having a fun conversation with you.

How do I use these questions?

I would refrain from introducing your questions or informing your suitor of their existence, but you should sprinkle them artfully throughout your conversation. Give your new friend a soap box and seem interested in what they have to say.

The purpose of developing a list of questions is for an instance wherein the conversation lulls and you would like to learn more about the person before completely writing them off. 

Although I once was the type to dismiss someone if the conversation was not immediately engaging, I believe in some cases, we all need a little bit of help to open up. 

Take this guide as a reminder that all hope is not lost if your suitors aren’t immediately participating in your niche bits and carrying on conversations about your specific interests. Perhaps there is something worth uncovering beneath their first-date jitters. 

With that, dear reader, please put on your writing hat and embark upon your inquisitive little journey. Bon voyage!

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