09/17/2014 12:55 pm ET Updated Nov 17, 2014

Confessions of a Divorced, Empty-Nesting Online Dater

Shutterstock / mtkang

About 18 years ago when my son was just two years old I went out for a wonderful dinner with my father. That may not seem like something worth writing about, but it was my first dinner out without my son since he was born, and so for that reason alone, it was a really big deal.

I had spent the last two years covered in baby food, baby spit, baby vomit, baby excrement, and well, just about every kind of goo associated with babyhood. And despite loving being a mom, I spent most of my time feeling tired, dirty, fat(ish), slug(ish), and was just plain wiped out. Mostly, I didn't feel like myself, and I was yearning to feel whole again, to feel attractive, to feel like me. Since I was a single mom I had no one to remind me that I was still a human being under all those layers of goo. So my father, no doubt having pity on me, offered to take me out to dinner, without my son in tow, and I joyously and graciously accepted.

He even offered to watch my son while I showered! I couldn't remember the last time I'd showered alone, and actually could take the time to blow dry my hair (the back as well as the front), and put on makeup. I then did the unimaginable and dressed in real grown-up clothes - not one stitch of Spandex adorned by body.

I'd been somewhat depressed for months. I was newly single, and having just completed a master's program in social work, I was still unemployed, and living with my father at the age of 35. While a nice dinner out and adult conversation wasn't going to solve all of my problems, it was definitely a step in the right direction.

So on this night I vowed not to ponder how I thought my life would turn out differently, or question every decision I'd made since childhood. Rather, I was going to trust that the babysitter wasn't going to detach my son's retinas in the two hours I was out, and determined to allow myself a guilt-free grown up meal, I hugged my boy goodbye, and walked out the door.

I sensed something was different the moment we were seated in the upscale restaurant. People were staring at me. I had been rather used to that type of attention before my pregnancy - in fact, it wasn't unusual for me to walk into a room and have men turn their heads. But that seemed like eons ago, before my pregnancy and motherhood had left me feeling anonymous and invisible. Having men notice me again made me feel normal; like a real a woman. So I decided to be self-indulgent for a few short hours, and enjoy the attention.

After about 10 minutes though I was becoming somewhat uncomfortable. At first I only noticed men staring - they smiled (smirked?), and I smiled back. But then I noticed women staring too - now that's odd, I thought to myself. Jealousy? Perhaps. I did look pretty darned good. Just enjoy the attention, the voice in my head admonished - stop questioning it; you deserve've worked hard, you never sleep, and you live under a constant layer of goo. Just enjoy being fawned over a bit. And so I did.

When a very nice looking man walked by our table and smiled at me (chuckled?) I practiced my long-lost art of flirtation and brushed my hair back with my fingertips, peeking up at him and smiling through my longish side-swept bangs. And that's when I felt it. With my face frozen into a half-smile (grimace?), I subtly and gently felt the back of my head, fingering what felt like, yep, a large Tootsie Pop wound tightly throughout my hair, with the stick protruding like a pop-up turkey timer.

So the reason for all of this attention wasn't because I had recaptured my lost feminine allure, but rather, because I had my son's large Tootsie Pop sticking out the back of my head. I wasn't being noticed because I was attractive; I was still the same old goo-soaked invisible mom (of the most incredible child in the world). In that moment, the insecurities of my youth came rushing back to me and I suddenly felt very out of place, like I just didn't belong or quite measure up.

I'm not sure what felt worse, the fact that I hadn't noticed a large-stemmed wad of hard wet candy stuck to my scalp, or that I had allowed myself to get all pumped up over the excitement of feeling attractive again for the first time in almost three years. Regardless, I felt awful. And yet, I also couldn't help but laugh in a my-life-is-a-really-bad-sit-com sort of way.

I remind myself of this very humbling (humiliating?) experience every time I start to place my confidence and sense of self worth (and sense of me) in something as transient as perfectly applied make-up and litter-free hair.

Fast forward 17 years. My son is now 19 years old and away at college, and for the first time in about 20 years I'm on my own attempting to navigate the world as a single empty nester. Despite all of these years, a boatload of experiences, and more than a decade of being in the professional workforce, the thought of dating again left me feeling the same as I did that night at the restaurant - a bit out of place and not quite measuring up, in a I'm-20-yards-behind-the-starting-line-of-the-race kind of way.

So I did what many people my age are doing and I joined an online dating site "just to see." If I could get through creating the online dating profile, then the actual process of dating would be a breeze, I reasoned as I went through page after page of questions about what I did for fun (sleep), what hobbies I had (drinking Starbucks coffee, and well, sleeping), and what my favorite hot spots were (Trader Joe's, the dog groomer).

I must admit that completing a personal profile for an online dating website can really shake one to the core. I'd spent the last 19 years raising a child alone, working full time while earning a master's degree and then a PhD. Fun for me was finishing the dishes before midnight. Also, I don't believe I'd heard the word "hobby" since circa 1978.

Browsing through hundreds of dating profiles didn't make me feel any better about myself, and actually, most of them made me feel much worse. I discovered that there were essentially two groups of people out there in my age category - those who lived in their mother's basement with a sleeping bag and an old PC, and those who lived very exciting lives that I knew nothing about, where with 'athletic and toned' bodies they hiked and biked and camped and bungie jumped and rock climbed and water skied and snow skied and surfed and fished (there's a whole lot of fishing going on out there), and in their down time, they jetted off to "hot spots" around the world on a moment's notice. This was not my world.

I've had a good life filled with love, adventure, companionship, and heartache, and loss, and a tremendous amount of hard work. I've spent a lot of time feeling loved and cared for, but I've also spent a fair amount of time feeling as though I didn't quite fit, didn't quite belong, didn't quite measure up, and dating in my 50s wasn't helping. So I grabbed a Tootsie Pop and a glass of wine and I pondered.

Who the heck has time for so many interesting hobbies and fun adventures amidst raising kids, working, paying bills, doing laundry and watching all of the Real Housewives shows?! Not me, that's for sure, and I strongly suspect that most of those other empty nesting online daters didn't either. Maybe their profiles were just good sales pitches, a best-foot-forward approach to creating the illusion of a life they thought had passed them by. I don't know, but what I do know is that at this point in my life, the only option available to me is complete transparency and authenticity - in all areas of my life, with myself and with others, including potential dates, and while those profiles sounded over-the-top exciting, they also made me feel like taking a nap by the second paragraph.

So here is an important life lesson I've learned as I enter my empty nesting years as a single woman in search of meaning and hopefully, at some point a partner:

Whether male or female, divorced or married, many of us coming out the other side of the parenthood journey may find ourselves feeling a bit off-kilter, and not quite ourselves, and perhaps even feeling a bit left behind. We also may feel excitement about what the future holds, and anticipation about what a world without constant parenting responsibilities looks like, but these emotions are probably punctuated with the intermittent pangs of angst and doubt.

As we struggle with finding new identities amidst all of these life changes, problems are more likely to arise if we base our sense of self on the superficial and fleeting, such as our physical beauty, our hobbies, our action-packed adventures, or our ability to remain at or ahead of the starting line.

Now this isn't an excuse to get lazy, boring and fat (I tell myself daily). But when I was in my fashion-trending 20s I didn't have the wisdom I now have in my 50s, and if I had to choose I'd opt for being the woman I am now - a middle aged woman with no hobbies, who isn't completely sold on this whole outdoors/nature/adventure thing, who doesn't really care about jetting off to a Mediterranean white-sand beach resort (although that does sound really nice), but who does care about learning and growing, gaining wisdom and creating a life of meaning and tranquility, while surrounded by really good people.

With each passing day I am becoming more okay with being way behind the starting line, because I'm just no longer all that interested in the race. In fact, I think I may just saunter along at my own pace, and hope that one day someone of value may want to saunter along with me.