3 Questions Worth Asking When Considering A Relationship With Someone

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Asking questions to get to know the person you are attracted to is an important step before you start a relationship. Most singles have a list of “must ask” questions and a few “should ask” questions. The primary goal of asking questions is to discover important things about the person in order to evaluate his or her compatibility with you.

We casually work our questions into conversation during the courtship phase.  Questions such as:

“What are you looking for in a relationship?”
“What makes you happy/sad?”
“What are your short and long-term goals in life?”

In addition to these run-of-the-mill questions, here are three questions worth asking when considering a relationship with someone.

Question # 1: “How long is the list of men/women you are talking to at the moment and do you have a short list?”

You should never assume that the single person you just met does not have other potential prospects. When someone responds positively to your advances, do not mistakenly think that you are exclusive. Most singles keep their options open and that is perfectly okay. The single person you just met was not sitting at home idle waiting for you to show up. The same attributes which attracted you to that person, most likely, has not gone unnoticed by others. You may have potential prospects yourself and you should be prepared to discuss your list as well.

Asking this question signals that you are mature enough to respect the independence of the person you are interested in. It is a sign of respect for a single person who is keeping his or her options open and also in recognition of the fact that, you have to prove yourself if you want to earn the right to exclusivity.

This question, in particular, is my favorite to ask as it helps me to gauge the other person’s level of interest. If she is talking to five other interested parties, I have to ask myself if I want to stay and compete. Maybe she is scared of getting hurt again so her options are always open. Maybe she enjoys the attention from men and is not ready to commit to anyone.  Maybe she is an indecisive person. I ask about the existence of a short list because I want to know if the person is seriously considering one or two of her prospects.  If she does have a short list, I will most likely, not stick around.


Question #2: “If I asked your ex-partner the reason for the breakup, what will his or her version of the story be?”

We all want to know what led to the breakup of our love interests’ most recent relationship. Women especially want to know if there was cheating involved. The men want to figure out who cut loose this ‘hot chick’ and the reason why. Everyone has a specific reason why they may want to ask this question. I get this question frequently from women.  Hardly am I asked to explain the break up from my exes’ standpoint. I was once asked this question on a date and I found myself struggling to explain my ex’s point of view. I was full of confidence as I plowed through my account of what led to the breakup. In a way, I concluded that I may have been self-centered in that relationship because I could not explain her side of the story.

You ask this question not to doubt the story the person told you but rather to determine his or her ability to understand others. This question can offer insight into how a person will act in times of disagreements or conflict. It serves to gauge a person’s ability to listen as well as to understand another’s point of view. I am looking for what conflicts there are in both accounts of events. I am trying to understand how well you articulate the flaws someone else saw in you. I am trying to understand how well you take criticism and your ability to learn from your mistakes.

Question #3: “Who are the most important people in your life?”

We always assume that a person’s family are the most important people in their lives and so we hardly ask this question. There are, however, other people who played or continue to play a significant role in a person’s life. For some, their parents or family members were not good role models. For others, it was and is that stranger who took them in as a child raising them as their own. It could also be that pastor who assisted them through a very difficult time in their lives. This question is a way of showing interest in the person as a whole. In addition to understanding a person better, it allows you to assess his or her ability to form close relationships.

This question also provides an excellent way to know how a person relates to their family. If they have very negative things to say about their immediate family members, you may stumble upon a character flaw you missed along the way. Marriage is the merging of two families. This question allows you to make an assessment of your potential extended family dynamics should you choose to tie the knot one day.

There are many questions that can be asked during courtship to help you to better assess your potential partner. These three questions, in my view, create an opportunity for more meaningful conversations that will allow you to gain valuable information about your love interest and help you determine your level of compatibility.

By Kwadjo Panyin…


Author: Kwadjo Panyin

Kwadjo Panyin is a Ghanaian born relationship and lifestyle blogger located in Los Angeles, California. He holds three degrees; a Bachelors degree from Rutgers University in New Jersey, an MBA from Franklin University in Ohio and a Masters of Science degree from Northern Kentucky University in Kentucky. Kwadjo is a business professional who blogs for fun. His articles are about the challenges of dating and relationship anomalies. Writing, blogging, world travel, and photography are his favorite hobbies.

1 Comment

  1. Prosper Dzitse says:

    This has been very helpful.

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