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Why You Should Ask a Date if They Are Crazy

As a single woman in her 30s, I’ve gone on my fair share of good and bad dates. Time after time, I have found myself trying to make conversation to get to know someone. These first dates are rarely not NOT awkward. As a counselor, I pride myself in being able to make a quick connection with people but these dates are always different and can remain awkward despite my best efforts.

That being said, there is something I love to ask my dates.

“Are you crazy?”

Obviously, by the time I ask the question, they know I’m a counselor. However, I suggest all women ask this kind of question. Their reaction tells me a lot as a woman and potential mate.

One potential response is anger or annoyance. This is a huge red flag. If a person cannot identify the humor in this type of question then this should tell you something about their ability to be a friend. John Gottman’s research states that marital friendship is a cornerstone to a healthy marriage. This capability can be shown in this type of question. Another reason is that it gives you a lot of insight into their ability to recognize that their are places in their like that isn’t perfect. If we are honest with ourself, we all have areas of our lives that are less than perfect. Areas that we need to work on. The ability to recognize that in ourselves and others is important. Studies have shown that people in long-term relationships have a higher level of receptors in their brain that indicate empathy. Being able to recognize the flaws in ourself and others one way to build empathy. A person that can answer this question with humor and honesty, is a person worth a second date.

I would also follow it up with another question.

“Will you tell me some the ways you are crazy?”

This is very honest question. As I wrote about above, the ability to be able to identify some ways you could improve is important to knowing the emotional health of your date. I will usually make a joke or comfort the date in some way by saying that the we all have areas that we would like to improve. It can also serve to reveal any potential “deal breakers” in the relationship. If they name something that is a “pet peeve” or cannot be changed and you are uncomfortable with it, this can help you recognize it early on.

I would then be prepared to answer the question myself. I do not expect my dates, nor should you expect yours to take a one-sided approach to this line of questioning. If the goal is to connect with a person, then being open and vulnerable is also important in the process.

“In order for connection to happen, we have to allow ourselves to be seen. Really, truly, deeply seen.”-Brene Brown

I am not advocating for you to “air all of your dirty laundry out” on the first date. Having an honest but appropriate answer to this question allows for connection to be made. If you are going to ask the question, come prepared with a answer for it you are comfortable sharing with someone you are getting to know.

While it may seem silly at first to ask a first date if they are crazy, the benefits outweigh the potential risk of embarrassment. Posing this type of question in a gentle, joking manner can help ease any potential tension that may occur. Seeing a potential mate’s character is a goal of this type of question. I think we can agree that this question reveals a lot no matter the response.

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