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What I Learned About Dating (Part One): Your Degree Of Success Is Directly Related to How Ready You Are

Today’s entry is somewhat of a hybrid between a blog post and a draft of a chapter of my book.

When I last posted, I mentioned that my book will be a series of essays about my personal experience and what I’ve learned on a variety of subjects. I plan to set it up in terms of topics, inspired by one of my favorite books: The Prophet, by Kahlil Gibran.

The topic which is most on my mind today is dating, so I’ll begin there.

Just to be clear, this isn’t meant to address how to find love or a relationship, necessarily. Rather, it’s a snapshot of what I’ve learned (so far) through my recent experience of dating. What I’ve noticed about myself… the dudes… what works… what doesn’t… and how I have evolved, over the course of the past couple of years, being single.

First, a couple of disclaimers:

  1. I am a woman and this is coming from my own perspective and based only on my unique, personal experience as a female. 
  2. As my recent dating experiences are taking place in my early 50’s, I can’t be sure that my insights will be true for women of all ages. 
  3. While some of my experiences of dating happened organically, the majority of the men I have met recently are from Tinder.
  4. I’ll only have time to address a few of the items on my list for this post but, rest assured, it will all be covered when the chapter is complete.

Let me start by explaining why I decided to use Tinder as a platform.

It’s pretty simple, actually: My friend made me.

We were sitting and chatting over pho and the subject of sex and dating came up. When I told her the last time I had a “date” she basically took my phone out of my hand and set up the app for me, there and then. She started me off with a few matches, coached me a little and then said:

“There’s your man. He’ll keep you busy for the rest of the night.”

And he did… as well as several other “matches” I found :)

So, here’s what I’ve learned about dating so far:


This may seem obvious but it’s so incredibly true.

A couple of years ago, when I came on the dating scene for the first time in 30 years, I didn’t enjoy the experience at all. As much as I “wanted” to be ready, I just wasn’t. I was still reeling from a very difficult divorce, a recent breakup from a subsequent relationship and struggling with guilt for screwing up my kids’ lives. I wasn’t yet settled in a house that felt like “home”. I was still in flux about earning a living and how to balance that with my life as a single mom. Most importantly, I hadn’t yet discovered the secret of Self-Love.

So, I took a break from dating for a while until I could get that stuff sorted out. I focused on falling in love with myself and being comfortable with my life as a single woman, entrepreneur and mom. During that time, I told myself I was “open” to meeting someone but that “someone” didn’t come along. The truth is, I wasn’t that open. In fact, my vibe was completely the opposite. Nobody seemed even remotely attractive to me. I couldn’t “see” myself with any of them. I was unconsciously sending out the signal of “danger, do not pass”.

The whole idea of dating just felt felt like a lot of work and I wasn’t prepared to invest in it. After all, I’d had relationships in the past where I invested pretty much everything I had… and it still wasn’t enough. I was much more interested in investing in things or people who provided a return on my investment… myself, my kids, my friends, my work… And that choice has proven to be extremely worthwhile.

Yes, I felt lonely and romantically discouraged for a lot of that time, but the more I invested in me, the less those gremlins crept in. The space in my heart was beginning to fill with meaning, connection, purpose, creativity, joy and gratitude. I was discovering that I had the courage to stretch myself and expand my limits and, in doing so, I began to find myself face to face with the incredible woman I was becoming.

Eventually, I began to take stock of whether or not I was ready to actively invest in dating again. I imagined what it would feel like and look like. What would I want? How would it effect my kids? My friendships? My work? What would work for me? What wouldn’t? I realized that I was much clearer than I used to be on all these things and that my boundaries were healthier and my needs simpler. I realized that I had let go of the possibility of getting back together with my ex (that was huge).

The coolest thing, however, was that each time I looked in the mirror or watched a video of myself talking or vlogging, I saw a beautiful woman looking back at me. A truly courageous, talented, wise and loving woman who really is a “catch”. I realized that, despite my imperfections, a man would be blessed to have me in his life.

That’s when I knew I was ready.

And here I am.

My experience of dating now is dramatically different than before.

I’m “all in”.

I’m confident.

I’m patient.

I’m direct.

I’m spontaneous.

I’m intuitive.

I’m playful.

I’m generous.

I’m honest with myself.

I don’t take myself or the process too seriously.

I know my value.

I know my boundaries.

It doesn’t feel like “work”.

And the dudes are plentiful.

I mean, really plentiful.

Surprisingly so.

What I mean is that, I didn’t expect to meet so many men who are actual “contenders”. Funny, smart, handsome, tall, sexy, talented men who are easy to be with… as if we’ve known each other forever.

So many good “fits”.

And some who really turn me on.

And they’ve been out there the whole time.

And there are lots more like them, I’m sure.

So, why didn’t I notice them sooner?

The only thing I can attribute this to is that I’m different.
I’m open and I’m authentic and that makes it much easier to connect, on both sides.

This is the most fun I’ve had in a loooong time.

And that’s only possible because I’m finally (and deliciously) ready.

Well, that’s Part One of “What I learned About Dating”

Future additions to this chapter will include:

  • How to “chat”: The crucial balance between playful banter and meaningful conversation.
  • Why I don’t let new dudes read my blog
  • Why interpreting the positive feelings of early infatuation incorrectly will eventually sabotage your experience
  • The importance of being “all in”
  • Why paying attention to early dialogue will reveal what turns you on/off
  • Trusting your intuition
  • How long should a first date be?
  • How to choose the venue for a first meetup
  • How to capitalize on the initial excitement of meeting someone new online
  • Why I don’t do phone calls
  • Why to get dressed every day as if you have a date (even if you don’t)
  • The importance of being spontaneous
  • Clear communication and investigating assumptions
  • When and how to call “bullshit” on a dude
  • Why imperfection can be sexy
  • Danger zones in the early days
  • What to do if you feel your defenses go up
  • Deal Breakers

Stay tuned!