Dating on purpose and checking it twice

Confidence is the universal aphrodisiac. Women say it’s the number one trait they look for in a man, followed closely by humor. Men are essentially no different; a pretty girl who lacks confidence is like to a CEO with a limp handshake. In both cases you walk away dissatisfied feeling like you’ve been bait and switched.

Generally when most think of confidence they imagine someone who can speak in front of a crowd, control a room, look others in the eye. We like those individuals; we admire the types who can carry themselves and are comfortable in the spotlight. Another aspect of their attractiveness is how they inherently know what they want out of out of life; they have goals, plans, destinies and move towards them without detours or pit stops.

But confidence is far more than mere corner offices, world records, or laser like focus; a confident person also knows what she or he wants in a relationship.  They understand, taking into consideration their own habits, personality and worldview, who they mesh with and who they don’t. They have a foundational grasp of who they are looking for. They develop an outline of the person they want, going even so far as to specify physical attributes including height, hair color, and location.

But like anything we can get lost in the details and it’s at the extreme where things often turn interesting. Determination might be sexy, but obstinacy is a huge turn off.   A motivated individual who goes after what he wants makes for a great impression, as long as you’re the one he’s going after, but if you happen to fall outside those parameters, he’s no longer sexy, now he’s just picky.


After a failed marriage and several unsuccessful relationships following I finally came to an epiphany; there was only one commonality each of these relationships shared – me. Not one of these women knew the others, yet the relationships started – and ended- in comparable fashion. My dating life looked like a fishing tournament; I’d cast my line hoping something would bite. And not a believer of ‘catch and release’; as long as they were willing to stay on the hook I’d keep them. I was playing Pin the Tail on the Donkey with my love life instead of Battleship. But to do that I first needed to know in what direction to aim my sites.

Not too long before I met my Queen I decided it was time to get serious about dating, honestly I started looking at it like a business. And as with any business I needed to establish a goal, what was I really looking for? It was then where I brought out paper, pencil and got to writing. What qualities did I want in a woman? Much like my professional life, I left out no details; hair length, fashion sense, prior marital status, religion, kids; everything was on the table. Then came the most important and most difficult part, I labeled each characteristic either ‘Must Have’ or ‘Nice To Have’.

The Musts then became my deal killers which made it all the more important they be given serious consideration. She may score high on Nice to have, but if she came up short on the Musts I had to be prepared to end it before it got started.


I’ve offered the same advice to countless others, especially those who cry how “there isn’t anybody out there.” As if everyone with any quality has vanished or is already taken. It’s at this point where I ask them ‘Well, what are you looking for?’ The response usually consists of fumbled lines about how they just want someone ‘nice’, ‘athletic’, ‘positive’, ‘funny’, etc.

Buyer’s remorse feels remorseful because of the sensation that we ‘knew better’.  Take a car for example, it’s only after we drive our new car home and away from the pressure and emotions of the dealership that those feelings kick in after we’ve had time to reflect on how it doesn’t have leather interior, heated seats, or the sunroof that we had our hearts set on. Or we buy a Nissan Sentra when we really wanted a Honda Accord. The thing that really bothers us most are those feelings of foolishness at being too hasty, impatient, and recklessness.

I think dating can be a lot like that.

Most of us have this tendency to jump in relationships for no other reason than they satisfy some superficial abstract idea of what we want. It’s not that we set the bar too low, we don’t set the bar at all. We live in a time where couples start dating just because they like the same song. This cheeky approach to relationships reaches its tragic climax after the song ends and from the silence left comes the realization that nothing concrete remains upon which to build a future. That’s when we look in the mirror and ask, “why am I with this person?” All of us have been there. 


But the question then becomes, can our picture of the person we desire be too clear? Can we get so granular in our enthusiasm ‘not to settle’ that we checklist our way out of every relationship? Can the requirements we hope to keep us “on track”  and away from those who would otherwise waste our time be considered ‘picky’? It’s a word flippantly thrown around these days, especially as we get older and the job has yet to be filled. Because the longer we go the easier it is to start questioning the casting agent instead of the actors.

The answer, I think, depends on our Must Have list. It’s wise to establish guardrails that can keep us from careening off a cliff into another disappointing relationship, but if the characteristics we most cherish in another are those we believe offer us the greatest advantage and give us what we don’t currently have we will never be satisfied with anyone, if we can even find them. Our Must Have’s should never be qualities that we can take from or leverage.  Instead they ought to encompass qualities we have and respect most in others, principles and a moral fiber that resonate with our own, and someone who inspires us to become better, instead of those bourgeois qualities, which culture admires so, but only serve to satisfy our superficial hopes and dreams.


An interesting thing happened some time after the Queen and I met. Coincidentally she had created her own wish list prior to our getting together and one night we shared them with each other. It’s an exercise I highly recommend to any couple for numerous reasons. Yet what was most astonishing wasn’t discovering what each was hoping for, it was instead learning how much we each possessed of the other’s hopes. For us, it simply reinforced what we already knew to be true.

None of this should be taken that once you put something on paper UPS will deliver the love of your life next week. We all know it’s not that simple, but what I am living proof of is this, you’ll never find what you’re looking for until you find out what you’re looking for.

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2 responses to Dating on purpose and checking it twice

  1. I know just what you mean. I had a mental list of what I wanted in a guy. The physical parts weren’t in the must haves (apart from being tall). I realised that if I did that, I’d never meet my soul mate. I tell other women that their ‘dream guy’ is not a real man. He only exists inside their head because they made him up. This of course, relates to the physical ‘look’ of the guy.

    My must-haves were mostly fundamentals of the way I think. I don’t like smokers, guys who don’t keep their word etc. The first time I realised I’d met the man of my dreams was when he got caught in traffic on the way to pick me up for our first date. He didn’t have a mobile phone with him, so he stopped the taxi he was in outside a phone box, dialled my home number and told me he was going to be 5 minutes late.

    After 16 years, he still calls me when his train is delayed and he’s going to be late coming home. I know this may be a simple thing for others reading this, but for me, this was an indication of how trust-worthy this man was – a quality that was top of my must-have list. I’ve had too many let downs in my life, too many pain and hardship. I needed someone in my life who I could place my trust in.

  2. Kyle –

    Great article! I went through the same exercise after having the endless dating of not working. It helped me to have focus on what I really wanted and after a period of time .. Grand Dude entered my life. And ooh-la-la … life took off.


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