Online Dating: Ignored Red Flags and Their Consequences ...

Dating in One's Middle Years #3

Red Flags - who cares!

What’s in it for You?

Welcome to the third instalment in my series on dating in your middle years. If you’ve missed the earlier posts, don’t worry—you can catch up with the first and second episodes here: Toe Back in The Pool and Free Fall.

If you’ve ever found yourself knee-deep in the strange world of midlife dating, where every date feels like a new level of absurdity, then you’ll appreciate this. In this third instalment, I delve into the surreal experience of a date that seemed fine - until it suddenly wasn’t.

This story takes a candid, often humorous look at the realities of midlife dating, where misunderstandings are common, expectations are rarely met, and sometimes, you’re left questioning whether it’s all just a cruel joke.

If you’re curious about the mishaps of modern dating or debating whether to go on that next date, or heavens forbid, join an online dating platform, you’re in the right place. Read on for a first-hand account of navigating the ups and downs of re-entering the dating pool.

Surviving a Date in a Noisy Restaurant

Despite my lingering misgivings and my male friend D’s shockingly poor advice to push past them, I somehow found myself arranging a third date. Looking back, at some level, I clearly knew it was a poor idea. You know, that feeling you get in the pit of your stomach when you mistakenly take a short-cut down a dimly lit street late at night.

Surely it’s not just me who does that?

So I grabbed my flagging sense of enthusiasm by the scruff of its neck and got texting!

After this brief exchange, we agreed to meet at the cinema the coming weekend; don’t ask me what we saw, it can’t have been memorable enough to recall. However, many of the other details of that night are burned into my memory!

We met at the multiplex in town and decided to kick off our evening at a well-known chargrilled chicken chain.

One of the advantages of being older, with slightly dodgy hearing, is that in a bustling restaurant, you only catch about every third word. The downside? It’s bloody difficult to decide whether the conversation is engaging or not.

I nodded along, smiled where it seemed appropriate, and generally tried to appear interested, while my internal monologue was preoccupied with questions like, “What did she just say?” and “Does she really think I can hear her over this din?”

The Uncomfortable World of Midlife Dating Etiquette

Throughout dinner, there were several instances where she reached out and put her hand on top of mine. Now, in principle I’m not usually against a bit of hand-holding - if there’s a genuine connection. But in this case, I found it rather uncomfortable, a bit like getting your hand pinned under a full suitcase - awkward, but not quite painful. My mind couldn’t help but leap back to the sitting room incident where her overly amorous chihuahua had humped the life out of his unwilling stuffed giraffe.

Despite my best intentions, I still didn’t pull away.

I’ve reflected on the why of this many times; no matter how I dice it, it simply comes down to wanting to be nice—a recipe for disaster if ever there was one.

When you want to be nice, you can get trampled - now I focus on being good.

Yes, I realise how that makes me sound, but in my defence, I was left unsupervised. When you’re first getting back into the dating pool, your self-esteem can be in the toilet, so you really have no idea what you’re doing.

After dinner, we entered the auditorium and sat side by side in the dark. Our focus was entirely on the film, so there was no real way to gauge how the date was going, which, frankly, was fine by me. For the next two hours, I didn’t have to think, just watch.

The Promise…

The film ended and I walked her the 10 minutes back to her car’ which was parked in a hotel multi-storey car park. As we got to the driver side door, she stared intently into my eyes, then turned and climbed in.

“Phew” I thought, “Nothing too uncomfortable had happened, maybe D was correct after all.”

She started the engine, reversed out of the bay and then just before driving off, rolled down her window, and in a tone that may have been calculated to be seductive, casually dropped a bombshell:

“I’ll be sleeping with you on the next date.”

Now, I don’t know about you, but to me, that sounded less like an offer and more like a threat!

The whole thing felt utterly contrived, with no natural progression leading up to it. I stood there, floundering for a response, but thankfully she drove off before I had to come up with one.

Reflecting on Midlife Dating: Is It Worth It?

I walked to my motorbike and sat there, unmoving. After about 10 minutes, I began to attract some odd glances.

I fired up the throaty V-Twin, clipped her into gear, and drove home, the night air helping my thoughts to coalesce.

I reflected on how wrong this all felt. The unease that had been gnawing at me for days was now a full-blown alarm in my head, telling me to run for the hills. I should have called my female friends, who would have surely given me some sage advice. But instead, like a dog returning to his vomit, I called D the next morning and told him what had happened.

“Fantastic!” he exclaimed.

“How the hell is that fantastic, mate?” I asked.

“Well,” he said, “looking on the bright side, you’ll be getting some action.”

In no way did this feel exciting or even vaguely appealing.

Yet, somewhat inanely, I felt a weight of expectation.

I appreciate some of you may well be wondering, “What’s Mark whining about? It sounds like he’s in for a good time.”

As usual, my capacity for looking at problems from all angles roared into overdrive.

No matter how I considered the issue, I couldn’t see a way out of my dilemma without creating offence. So, with many misgivings and feeling like a complete cretin, I went ahead and arranged a fourth date. Dinner at mine.

What could possibly go wrong?

The Last Supper: A Date to Remember

The day of the date arrived, and with it, my anxiety hit new peaks. As I prepared for what felt like my own “last supper,” I couldn't help but wonder if this was how Jesus felt before heading off to the Garden of Gethsemane—aware that something was about to go terribly wrong, yet determined to see it through.

Still, I soldiered on and headed out to buy ingredients for supper, settling on a king prawn and avocado salad starter, followed by ribeye steak and garlic mash with romaine.

The hour of the date crept up on me before I was truly ready. After a frantic apartment cleaning session—including changing the bed linen, removing every speck of dust, and tidying the place within an inch of its life—I was as prepared as I’d ever be.

Then, the doorbell rang.

I opened the door, and there she was—resplendent in wet-look, skintight trousers and a top that did very little to conceal her... assets. As soon as I closed the door behind her, I was pinned to the wall, and her tongue plunged into my mouth. I was caught completely off guard, and before I could even process what was happening, I was hauled into my bedroom.

An Unforgettable Bedroom Encounter

Now, I wasn’t exactly feeling the moment, but she was clearly in an amorous mood. What followed was… well, let’s just say it was A Night to Remember. Not in the sense of the 1958 film classic—though I did feel like I was sinking fast—but in a way that will forever stay with me for all the wrong reasons.

My clothes were rather skilfully removed, and as things progressed, I found myself providing a certain kind of attention that, in a fair world, would be reciprocated.

To put it delicately, it was a bit like using a self-service checkout—you expect a smooth, automated process, but instead, you end up doing all the work while wondering if there’ll ever be any reward.

As matters progressed, and far sooner than expected, her thighs clamped down around my head with the force of a hydraulic press, and I half expected my eyeballs to pop out like a cartoon character. For a moment, I thought I might never escape. When I finally emerged, dazed and slightly out of breath, I climbed up beside her, hoping she might show some inclination to return the gesture.

No such luck.

She lay there in a state of post-coital bliss, clearly content to bask in her own satisfaction. It quickly became apparent that I was dealing with the most self-centred bedroom partner I’d ever encountered.

Uncomfortable Confessions

As we lay there, she began to divulge some rather surprising information.

First, she said, "I'm quite surprised I'm dating you. I normally only go out with large black men." Now, considering we were both stark naked and I don’t fit that category in any way, shape, or form, I was at a complete loss for words.

She then proceeded to tell me that at 17, she had lived with a 54-year-old man and that she had once been a stripper.

No judgement, but this litany of self-disclosure continued like some diabolical machine gun! I wasn’t sure if this was her way of oversharing in a relaxed state or if she just felt she needed to get it all out now.

After what felt like an eternity of awkward revelations, she suddenly sat up, stretched, and said, “I’m really hungry. Can we eat?”

Feeling compelled and irritated at my own lack of assertiveness, I pulled on my clothes in something of a disconnected trance, and spent the next 20 minutes sorting out supper. She ate with gusto, and about ten minutes later, she mentioned she had to get back for the dog.

At the front door, I mustered the courage to say that I was feeling a tad ‘unrequited’ in the bedroom department. She giggled and gave a nonchalant “next time,” and slid out the door.

I stood there for a few minutes, replaying the entire evening in my mind, each awkward moment snap-shotted like a slow-motion car crash. With a frustrated shake of my head, I decided to fall back on routine - anything to brush off the feeling of being used.

First up, I stripped the bed and tossed everything into the wash - not because of any concerns about her hygiene, but more out of a desperate need to cleanse myself of the night’s events.

Next, I did the washing up and tried to distract myself with some mindless television. But no matter how many channels I flicked through, I couldn’t settle. The events of the night were still looping in my mind, refusing to let me relax.

Eventually, I remade the bed, hoping a sense of order might bring some peace. But as I lay there alone, my body betrayed me, leaving me with a rather inconvenient problem - one that, like the rest of the evening, I’d have to handle on my own. With a resigned sigh, I turned back to my self-service analogy—just another task in a night full of doing all the work.

At least this time, I managed a small but solitary reward for my efforts.

After that, I finally fell into a fitful sleep, my mind still tangled in the knots of the evening.

The Morning After: Facing the Fallout of Midlife Dating

I woke up the next morning with an abiding sense of disquiet, like a troubling dream that clung to me like a fog. It was that unsettling feeling of being a participant in something you couldn’t control—aware of the mistakes you were making but powerless to change them.

I knew I couldn’t go through with a repeat performance. The very thought made me feel nauseous with anxiety. There was no getting away from it—I had to let her know.

But the prospect of that conversation filled me with dread.

I spent over an hour drafting and redrafting a text, each version somehow worse than the last. Finally, I realised no text could convey what needed to be said, so I decided to call. It was still early, and part of me was praying she wouldn’t answer.

As hoped, the call went to voicemail.

“Hi, it’s me,” I began, wincing at how flat it sounded. “It’s been great getting to know you, but I’ve realised that emotionally, I’m in no position to date right now. This is going to be my first Christmas without my kids, and I’m starting to see how much it’s going to affect me. I’m really sorry to mess you about, but I think it’s better if we don’t see each other again. I hope you understand, and I wish you nothing but the best.”

I hung up, feeling a mix of relief and guilt. The words were out there, and now all I could do was wait and hope she took it well.

I heard nothing for an hour and a half. The silence was deafening. Eventually, I called D to bring him up to speed. Predictably, he laughed hard - what a mate!

“I’m never asking you for dating advice again,” I said, exasperated. “I followed it to the letter, and now here I am, up shit creek and paddling with my bare hands!”

He asked what I was complaining about -I’d gotten laid, hadn’t I? I pointed out that was factually inaccurate and it was hardly the grand experience he imagined. The whole thing had been traumatic, and her being the most selfish person I’d ever encountered in bed left me feeling used.

Telling him he was officially “off my Christmas card list”, I ended the call.

I made a coffee and sat in silence, stewing in my own thoughts.

Then, suddenly, my phone binged with a message alert.

The Message from Hell: When Midlife Dating Takes a Dark Turn

My heart skipped a beat. I stared at my phone, too terrified to pick it up. Minutes ticked by as I gathered the courage to face whatever was waiting for me.

Finally, with a deep breath, I summoned the bravery to read her reply.

Her message was succinct:

• “Bastard, I feel so used” (She felt used! Jesus H. Christ, was she kidding?).

• “You are the most fucked up individual I’ve ever met outside of a loony bin” (She worked in mental health, so I began to feel some pity for her charges).

• “I hope you have a shit Christmas—fuck off.”

Suddenly, she didn’t seem to have a problem communicating, and I couldn’t help but wonder if her various engagements with me had been part of a calculated plan. This unsettling thought sat with me for a while before I dismissed it.

Women don’t act like that. Do they? I must be imagining it.

Still, the whole thing left me rattled. I decided it was time to call someone who was less likely to give me poor advice - P, a solicitor friend. Somewhat embarrassed, I recounted the entire sorry incident and asked what I should do, bearing in mind that she knew where I lived. He made a wry comment and told me not to worry, but to keep all the messages - just in case I needed them for the police later.

WTF!

How reassuring.

Reflections and Learnings: The Perils of Midlife Dating

Looking back, I realise just how many red flags I’d seen yet ignored. I knew something was off, but like so many of us navigating the murky waters of midlife dating, I let politeness and a desire not to offend guide my actions instead of trusting my instincts.

The signs were all there:

• The oddities of our first date, including her unsettlingly intense behaviour

• The Family Christmas invite after an hour

• The dog poo incident on the beach, which she completely disregarded.

• The shared food incident at the café, where her dog licked her meal and she thought nothing of it.

• Her mother visiting daily to close the curtains, which seemed bizarre for a grown woman.

• The dog’s tooth extraction story - who does that!

• The sexually abused giraffe toy, which added a disturbing layer to the already uncomfortable situation.

• The casual threat that I’d be shagged on the next date, delivered with a predatory undertone.

• The self-focused nature of our engagements, not just in bed, where my feelings were clearly secondary.

• The odd and late disclosures about her past.

Despite all this, I’d ignored my gut feelings and pressed on. Apparently, it’s a classic mistake, especially in midlife dating, where the fear of being alone or the hope that things will improve can cloud your judgment.

So here’s the question I pose to you, dear reader:

1. How many red flags have you ignored in your dating life?

2. How often have you let someone’s charms or the simple fear of being alone lead you down a path you knew wasn’t right?

The online dating industry sells us the dream of finding love with just a few clicks, but they rarely mention the emotional minefields you might stumble into along the way.

It’s easy to get swept up in the excitement, but perhaps it’s time we all took a step back and trusted our gut feelings a bit more.

Stay Tuned: Next Week’s Episode

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Spoiler: It’s not straightforward, asking out the friend of a friend.

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