Start (and End) With Why In Dating

A few years ago, I was introduced to the concept of “Start With Why” by Simon Sinek. The basic idea is to assess underlying motivations before beginning an endeavor. While its application is primarily focused in the business and marketing world, it is useful in most every sphere of life, particularly to a reflective creature like myself. What is my motivation for choosing one thing over another? Answering this question upfront can be a great filter to avoid heading down the wrong path entirely, even if the “what” (end goal) is worth pursuing.

As one still involved in the realm of dating, I’ve realized over time that the principle is particularly useful in that setting. Confusion abounds in my generation regarding the whole process. Friends and I have spent many a night discussing the opposite sex and whether there is a “right” way to approach the matter. I can’t help but think we would have avoided some of the perplexing scenarios if we had sincerely assessed our motivations beforehand.

It takes a brutal amount of self-honesty (a skill which I have yet to master), to start with why, but stop and ask yourself, “Why am I interested in this person?” On some level, it will be physical attraction, but is that the primary driver? Are looks dominant in the face of other factors that you know make a long-term relationship unlikely? Are you attracted to something in this person that is drastically different from yourself? Why? Are you just lonely and want someone? The answers to these questions can be hard to face, but if one is dissuaded from pursuing something unwise, the savings in time, effort, and trouble downstream are more than worth the discomfort.

Conversely, the “why” can be affirming, giving a green light to go for it. Maybe the attraction is based upon solid character qualities. Perhaps outer beauty is coupled with common interests and goals. Even an ambiguous answer need not be construed as negative so long as it’s honest. Sometimes someone really does just have a kind smile that makes you want to know them more. At least be aware if such a sentiment is your sole basis for acting. Then pursue dating if the “why” seems wise.

The more I thought about it, however, the more I realized that not only starting, but also ending with why is helpful for everyone involved. Dating is a process of exploration and collecting information. Ultimately, this information is used to make a decision: do I continue seeing this person or not? Having been on both sides of that decision over the years, I have never experienced an instance where ambiguity was helpful. It may be my strong tendency toward thinking (as opposed to feeling), but I genuinely appreciate knowing why things didn’t work out. The older I get, the better I am able to accept such information without taking it personally. Though my track record hasn’t been perfect, I always try to extend the same courtesy to others if they care to hear it. (Some don’t.)

The answer for why one is choosing to break things off can be even more uncomfortable and revealing than the initial motivation. After all, this is a person you presumably had some interest in, so what changed? Does her personality clash with yours? Does he seem flighty and unsure what he wants in life? Have things with another love interest progressed? Do you not find her physically attractive after the initial thrill wore off? The answer could be that you honestly can’t point to a specific reason; you just feel it. At least own the fact that you are deciding based purely on emotion and nothing quantifiable. Then share that information with the person if they want to know.

Of course, nobody likes to tell someone what they don’t like about them, but there are polite ways to say just about anything. “I’m just not that attracted to you,” doesn’t mean “you’re not attractive.” It means that the speaker personally is not attracted, and a mature adult will receive the message as such. Be aware, however, that your reasoning may say far more about you than it does the other person. Are you really breaking things off because they double-dipped in the salsa at dinner that one time? Acknowledging harmful tendencies is a starting point for fixing them. I’ve found that this practice brings unparalleled self-discovery and closure, often making it easier for both to move on with as few hard feelings as possible, certainly compared to giving no explanation at all. It may not always be pleasant, but if we’re all adults, I think it’s the most respectful way we can treat one another.

Starting with why is a helpful filter to begin. Ending with why is the clearest and kindest way to conclude. Dating in today’s culture is difficult enough without the damage of thoughtless pursuits and loose ends. Still, if my generation will take the time to reflect on what is driving us to make the decisions we do, just maybe we will end up with more clarity in an arena that has become all too ambiguous.