Exploring Online Dating at 48: The Dilemmas of a Sober Single Woman Navigating Digital Love

Ah, 2024. The world is a different place now, and so am I. As I sit here, hunched over my trusty sticker covered laptop, my fingers lightly dancing across the keyboard contemplating writing a new dating profile and “getting back out there,” I can’t help but cast my mind back to the year 2018. Ah, pre-pandemic dating. It was a simpler time, a time when face masks were a skincare routine, not a social necessity. A time when the word “Zoom” was nothing more than an onomatopoeic term used in comic books. And it was also the last time I really dabbled seriously in the chaotic world of online dating. To be clear, I’m not saying I haven’t dated since then, but the dates have been far and few apart.

The modern dating landscape, with its multitude of platforms and apps, is a veritable minefield of missteps and faux pas, a reality that I am all too familiar with. I’ve been doing online dating since the early days of the dot com boom. That nostalgic symphony of old-school dial-up internet still rings in the memory fault in my ears, as it starts with a dial tone’s hum, followed by high-pitched beep and robotic transitions into a lower pulsing hum indicating successful connection. #IYKYK I’ve been online dating (on and off) since dial up was a thing and, to be honest, I’m tired of it. The thought of another year of swiping left or right makes my eyes roll into the back of my head.

Let’s face it, if you have dipped your toe into the murky waters of online dating in the past decade (or two, A ‘hem) you are bound to have at least one cringeworthy tale to tell. In my case, my repertoire of dating disasters could fill an anthology, each story more absurdly hilarious and ridiculous than the last. The anecdote that I am about to regale you with, however, easily makes the top ten list of my most comically catastrophic dates.

Flashback to pre-pandemic online dating

Back in 2018, the time of this story, I had just discovered Bumble, a digital dating platform (app) where women made the first move. Like a modern-day Jane Austen heroine, I took the reins of my romantic life into my hands, diving headfirst into the virtual realm of swipes, winks, and emojis. My dating strategy? To bypass the endless flirting and meet my potential suitors in person as soon as possible. After all, what’s the point of witty banter if there’s no physical chemistry?

My dating strategy, honed through years of trial and error, was simple: cut to the chase. No endless texting, no long, drawn out phone calls. Just make a connection and then promptly arrange a face-to-face meeting. After all, chemistry on screen doesn’t necessarily translate to sparks in person. The plan was to meet for a brief encounter – a coffee, a drink, a walk – in a bustling public place to hopefully avoid ending up starring in a true crime documentary. The goal? To escape unscathed from a disastrous date within an hour. And if Cupid’s arrow struck? Well, extending the date or planning a second one was always an option.

And so, I found myself on a date with Stan (not his real name) – a handsome, polite, and seemingly normal individual. We convened at a swanky bar in downtown Bellevue. As I settled down into the modern egg-shaped lounge chair, he ordered me a Pellegrino with a twist of lime, while he went for a whiskey on the rocks. I’m old-school, and I do love it when the man asks and then places my order for me. I think it’s sweet, but I also don’t care if I order for myself. I have deal breakers; this isn’t one of them. My choice of a non-alcoholic drink usually raises eyebrows (dates sometimes get weird when they find out you don’t consume alcohol), but Stan didn’t bat an eyelid. Score one for Stan! Dating as a non-drinker can be tricky. And as side note, if you want to learn more about that subject specifically, you should read my friend Tawny Lara’s book, aka the Sober Sexpert, Dry Humping. You can thank me for this recommendation later.

“Dry Humping: A Guide to Dating, Relating, and Hooking Up Without the Booze” by Tawny Lara

Stan and I hit it off instantly, our conversation peppered with laughter and witty repartee. With his sharp intellect, amiable personality, and kind eyes, he was checking all the right boxes. Before I knew it, hours had flown by, and the once tranquil bar was now buzzing with the energy of a nightclub. A bit much when you trying to get to know someone and dating in your 40s.

Soon, Stan and I found ourselves bar hopping around downtown Bellevue, not quite ready to end the night. We’d found solace in a sports bar, exchanging stories of our past dating escapades over food and more drinks. Ok, so I was likely doing most of the storytelling, given my natural ability for the gift of gab and unconsciously dominating conversations. Despite the occasional distraction of the sports-ball game playing on the TV behind me, I was charmed by Stan’s attention and the unexpected kiss on the cheek. Up until this point, Stan was a gentleman and a real sweetie.

So far, so good…

As that night went on, we eventually ended up at his impressively large home in Mill Creek. Arriving at Stan’s house, I was taken aback by his impressive four-bedroom, three car garage home, filled top to bottom with Pier 1 Imports décor. Clearly this was before the décor retail giant went out of business, or possibly he bought out their inventory, I’ll never know. I was undeniably impressed, despite questioning why a single man with no kids needed such a large house and a dining room table staged with eight bedazzled place settings. Was the house too staged?

As we nestled into his couch, waiting for SNL to start on KING 5 NBC, my employer at the time, I was tickled pink that a commercial I had worked on for an event called KING 5 Konnected was airing, and it was the first time watching it live and not in an editing room at the office. I think Stan thought I was making that up. Playfully, as our flirtatious banter of flipping shit to each other was escalating into intense sparks, Stan leaned in for a proper kiss and I found myself forgiving him for his Pier 1 obsession and the beaded, sequined pillow scratching the backs of my arms.

As we continued our PG-rated make-out session (sorry Mom), I was repeatedly interrupted by the incessant buzzing of my Apple Watch. Ignoring it initially, the constant vibrations became impossible to overlook. Our make-out session was being interrupted by incessant phone calls or texts; I wasn’t sure which. As I politely put a little distance between myself and Stan, I found that I had multiple missed calls from Jennifer, my son Jakob’s stepmom, and Jakob himself. My heart pounded in my chest as worry washed over me. Something bad must have happened.


As my stomach dropped into a pit of anxiety, I politely excused myself from Stan and quickly returned Jakob’s call first. He sounded frantic, “Mom! Are you okay? We’re almost there!” Even after all these years, I remember how strongly his words took me by surprise. Almost where? And then he explained. Apparently, he had received an SOS text message with my GPS location attached. The poor kid thought something terrible had happened to me!

Even now, my mind races back to my list of health scares that Jakob has had to endure over the years. Sadly, it’s not a short list. In addition to being in long-term recovery from alcohol and substance use disorder, which came with all kinds of drama prior to putting the plug in the jug, I’m a real sober cat with nine lives. Back in 2015, I had suffered a near-fatal almost heart attack due to a 95% blockage in my LAD, earning it the name, ‘the widow-maker’. Ever since that time, I have tried to be vigilant about my health. The Apple Watch was intentionally purchased to monitor my heart rate. Little did I know, in the heat of passion, I had accidentally activated its emergency feature, sending an SOS alert to ALL my emergency contacts. The list was long, my friends, very long.

Jakob, along with his girlfriend at the time, his best friend McCabe, and his cousin Emma, were ironically or coincidentally at a nearby bowling alley. They had assumed the worst. They thought I was having another heart attack and had bolted from their bowling game to rush to my aid, almost forgetting to change footwear and taking the bowling shoes with them.

I quickly reassured Jakob, “I’m fine, Bubba. There’s no need to worry.” The relief in his voice still rings in my ears all these years later. He loves me. He really loves me. And if I remember correctly, it was followed by laughter as he and everyone in the vehicle with him realized the true nature of my ’emergency’. (Insert face palm emoji here #SOembarrassing)

It’s fun to be my son, except when it’s not.

We’ve both gotten milage out of this story of the years for very different reasons. Just pause for a moment and imagine what it’s like to be MY son. Looking back, that night was a hilarious mix-up. A simple misunderstanding led to a flurry of panic, but in the end, it provided a good laugh, well for everyone except maybe Stan. He was definitely not amused. It just goes to show, you never know what to expect when navigating the dating world in your 40s.

Those of you that know me, know my tendency to overdue things. Well trust me when I say my emergency contact list was LONG. I had to make many text explanations and phone calls to friends and family members telling them to stand down. And then, amid the flurry of texts, the actual 911 service called to verify my safety. I literally laugh out loud when I think back to Stan’s expression being far from amused.   

Once I wrestled the situation under control, which took at least 10 minutes, I turned to face Stan. His eyes bore into me as if I had sprouted a second head. I felt my face heat up with embarrassment. He asked if everything was alright, and I attempted to explain the mishap. In response, he wondered out loud, “Are the cops going to show up here?” I wished his Pier 1 Imports throw pillows that had been scratching the backsides of my arms during our PG-rated make-out session would swallow me whole.

Is it me? Am I the problem?

Taking a deep breath, I thanked Stan for the eventful evening. Clearly our time together had hit its peak. I suggested we wrap up our date, as I was feeling like my welcome was worn out. Stan responded, “You know, we could have gone to your house or scheduled a second date if you weren’t comfortable coming over here.” His puzzled expression prompted another question, “Do you often find yourself in these kinds of situations?”

Yes, Stan. Yes, I do. At times, I have no filter and I’m known to overshare. It’s an awkward tick that I pray my friends and family have come to endure with love but can be jarring to first dates. Perhaps I shouldn’t have regaled him with tales of my clumsy fashion week tumble backwards through the step and repeat or experiencing the triple bird poop incidents, including one at Disneyland. (Happiest place on earth, my ass!) I only recently learned from a friend that I shouldn’t be using these stories on first dates or telling first date stories on first dates. OOPS! #thatsawkward Does this mean I’m the problem?

With a plastered smile, I thanked him for the memorable evening and left him with the opportunity to ask me out again, if he felt so inclined. He did call and we did go out one more time. But that story, well that one’s just for me.

The Third Date Curse

And that’s where my third date curse kicks in and this story with Stan ends. I literally can not recall the last time a guy made it past the third date. It’s possibly been longer than a decade. Or maybe I should rephrase that to the last time I made it past a third date? Either way, it makes it really awkward to start dating now, because usually the first question that gets asked is “So, when was your last relationship?” What am I supposed to say, “Decades?” It’s honest, but not usually received well. The follow up question is usually “Why have you been single for so long?” Um, if I knew the answer to that riddle, don’t you think perhaps I’d have figured out alternative solutions by now?

On the drive home, I remember calling Jennifer, the mother of my son’s other brother, and relaying the night’s events. We laughed so hard that tears streamed down my face. She exclaimed between fits of laughter, “Only you could find yourself in such a situation!” And she was right.  

To Date or Not to Date, that is the Question

While my single status seems to be a constant six years later, my life is actually pretty great. So here I am post-pandemic, still sober, still single, slightly chubbier, and infinitely wiser than the version of my 2018 single self, still waiting for Mr. Right. As I contemplate whether I want to dive back into the dating pool or continue to enjoy my solitude, that crazy night is a stark reminder of how unpredictable dating can be. Yet, it also brings a smile to my face.

It reminds me of the fun, the laughter, and the joy that can come from unexpected twists and turns. Sure, dating can be a rollercoaster of emotions, but isn’t that part of the charm? It’s the unpredictability, the chance to meet new people, learn about their lives, and maybe, just maybe, find that special someone.

Yet, there’s also something profoundly comforting about being alone, about enjoying my own company. It gives me the freedom to do what I love, be who I am, without any constraints. It allows me to wait for that perfect soulmate to come along, without rushing or settling.

As I ponder over this to date or not to date dilemma, I can’t help but think back to that night with Stan. It was a disaster, yes, but also a night filled with sparks, butterflies, and laughter. Whether I choose to date again or continue to bask in my solitude, I know one thing for certain – I’ll continue to embrace the unpredictable moments, the laughter, and the joy that life has to offer. After all, isn’t that what it’s all about?

I know that love, like everything else worthwhile in life, cannot be rushed. It happens when you least expect it, in the most unexpected of places. Or maybe it won’t happen at all. I’m not responsible for the outcome, I’m only responsible for being in action. And choosing not to date is technically an action. So, with that, I plan to keep focusing on loving myself and not worrying about my happy ever after. And whether the future Mr. Bryson becomes a reality or not, I’ll keep writing, keep living, and keep laughing at the absurdity of it all, jokingly referring to myself with love as the “Sober Old Maid.”

Those of you that know my fondness for the Golden Girls and my dear friend Rita B. (may she RIP) will hopefully appreciate the love and sincerity of those three words “Sober Old Maid.”

This is my artistic way to law of attraction the future Mr. Bryson into existence. Clearly, he’s saving his heart for me.

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