Courtship Confessions: How to Deal with Old-School Dating in the Modern Era

Like many women, finding that right guy was a mystery to me for a long time. I’d gotten it wrong so many times in the past. I questioned my judgement. I questioned whether there really was someone out there who could handle all this sparkle.

Sometimes I even questioned my sanity for jumping back into the dating pool after several MAJOR fails.

Then, one night back in 2012, when I wasn’t looking for ANYONE, while I was on my way to a networking event, I said a prayer. I had just turned off my street, paused at a stoplight and said, “God, I just want to learn more about me. I want to be 100% authentically me...oh, and I want to travel.”

That was my deepest desire.

Because all my failed relationships were stepping stones on a search to understand who I was, what I wanted. And I was tired of living by other people’s rules as to what that would look like.

After successfully having a film that I co-wrote be produced and distributed, after successfully owning a private pilates business, after successfully taking a back stretching product to market…

It wasn’t success that I had a problem with...it was love.

Two hours after my prayer, while mingling with some people at Barney’s Beanery in Westwood, this guy with hair down to his shoulders, rings on nearly every finger, saunters up to me with a piratey swagger and asks me one question, “Are you single?”

In that moment, I was curious, but I honored my commitment to myself, to God, the commitment to live 100% authentic and truthful. At that moment I hadn’t talked to the guy I’d been dating in weeks, and he and I had already done the "on-a-break” thing, so I answered honestly, “I guess you could say I’m in an ‘it’s complicated.”

“Great, at least I’m not barking up the wrong tree, let’s grab a drink,” said the pirate.

For the rest of the eve, I kept up with my unabashed honesty, telling him the truth of how I really felt about everything from 80s music to cheating, sharing things that at that time even my closest friends didn’t know about me at the time. We talked so long that my car got locked in the parking garage across the street. Since it was before the time of Uber, he politely drove me home and offered to make me dinner the following next week.

I’d say six years later, and after celebrating our 4th wedding anniversary last month, it worked out pretty darn well. Right Spikey?

However, eight years of dating misfires, rocky relationships, and really bad choices, could have been easily circumnavigated had I had the knowledge, experience, and expertise of a relationship coach, like my guest in this week’s #QueenConvo, Laura Lee Wood.


Laura Lee Wood is an executive relationship coach, executive matchmaker and founder of “Nashville WingWoman.”

A former attorney turned executive relationship coach and executive matchmaker, Laura understands the unique challenges to attracting love while balancing a demanding career. And, the image you created in your career may have allowed you to achieve great success but the skills needed in your profession are not the same as what is needed to create a fulfilling romantic relationship.

Laura practices and teaches the art of traditional courtship. And in our #QueenConvo, we dive into dating, where to find a man, self-respect and sooooo much more.

Laura and I are in agreement, that you can have both career success and success in love. Her work helps single successful women do the deep work required to heal from the past and find a remarkable man to love and fo life with forever. Court adjourned.

And, even if you’re a happily married woman like me, just know, the courtship never stops. It changes, because there is no need to chase, but, even when you are married, you should always keep dating your spouse.

Share this with a special, successful single gal who could use some love in her life.