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Dating in One's Middle Years #2

What’s in it for You?

Curious about the mishaps of dating in your 40s and 50s? This story takes you through my laugh-out-loud misadventures, from misleading profiles to surreal second dates. Join me as I navigate the absurdities and unexpected twists of rejoining the dating pool. If you enjoy a candid and humorous look at love later in life, you won’t want to miss this tale!

Fixing My Dating Profile …

Having already ‘ridden’ the emotional rollercoaster simply to complete the first version of my dating profile, I wasn’t exactly overflowing with confidence that any subsequent ‘stab at it’ would improve matters.

So I did what any self-respecting, assertive, and outwardly confident man does…

I buried my head in the sand and ignored the problem!

A few weeks had drifted past unnoticed when suddenly, at the end of a particularly gruelling session of circuit training, two of my female friends cornered me, literally.

In a style more reminiscent of an interrogation than anything else, they applied the verbal thumb screws:

“How’s it going, gotten any ‘action’ yet?” from one;

“Been on any great dates yet?” asked the other.

I spluttered and confessed I’d mostly quit as it was proving to be more of an emotional drain than I’d imagined. It felt like ‘doom scrolling’ and I was wondering whether it was worth the effort required.

“Grow a pair!” was the response, and before I knew what was happening, my phone was grabbed and the dating app opened. Apparently, some ‘live-time’ tweaks were required to make my profile marketable.

There was a burst of thumb movements and some laughter… in under a minute, my phone was tossed back, and I looked at my profile.

‘Funny, fit and intelligent man. Enjoys bikes, keeping fit and nights out. Seeking a like minded individual for some fun dates and to see where that leads.’

I was then given more explicit instruction.

“Get matching, but don’t get catfished!”

I told them that I didn’t go fishing, so that seemed unlikely—and launched into an explanation of why I don’t like fishing.

I was stopped almost immediately…

“Mark, how is it you know so much yet… so little? Watching you try to date is like watching a newborn foal stumbling through the forest. Wise up, mate!”

If it’s true that ‘good friends feel comfortable trampling your ego,’ these two must be the best friends ever!

What followed was a detailed explanation of what ‘catfishing’ was … I was a little incredulous but felt that forewarned is forearmed, so I thanked them and went home.

Once more into the breach, dear friends, once more …

Following their advice and hands-on help, I decided to take another shot at online dating. It wasn't long before I stumbled upon a profile that caught my eye. She was about 10 years younger than me, so I found myself wondering why she would be interested. Nevertheless, I liked her photo (engaging profile and a gym gear shot); she responded within a few hours, and texts were exchanged.

I called D, a male friend, and he said I should just relax and see what happened. It sounded like logical advice so, reassured, I arranged a date for the coming weekend. I felt a moment of excitement, followed by several days of overthinking and some vague nausea … perhaps I wasn’t really ready to rejoin the ‘dating community’ quite yet.

I spoke to D again and he said that was normal and I just needed to push past those feelings and “Get back in the saddle!”

Quite the visual euphemism that did nothing to allay my concerns!

The First Date …

We arranged to meet for coffee at a local hotel, so, not wanting to be late, I arrived slightly early, choosing a corner seat to observe who came in. The time for our meeting came, and about 15 minutes passed. I began to wonder if I'd been stood up.

Suddenly, a woman I didn’t recognise stopped in front of me and said, "Hello, Mark, I’ve been sat over there," she pointed to a corner table, “waiting for you to come over.”

I just managed to avoid asking where I knew her from, as it dawned on me she must be the lady I’d arranged to meet; although, if it were the woman in the photo, it had clearly been taken many years and about four stone ago!

Just before anyone decides to go all ‘MMA’ on my arse for being ageist or sizeist, I’d like to remind you that technically, I was the ‘victim’ of false advertising.

I’d agreed to a date with the person in the photo, not the lady now standing directly in front of me!

Notwithstanding all of that, and in the nanosecond it actually took for all of these thoughts to fly through my brain, I responded politely, said, “It is a pleasure to meet you,” and ordered us some coffees.

Whilst her appearance had been a shock, I reminded myself life was a learning opportunity.

Hovering at the back of my mind was a nagging thought: if someone is that dishonest in their dating profile, it might indicate other problems.

Still, not to be deterred by appearances alone, I decided to stay, and whilst I didn’t find her attractive in the dating sense, she was funny and entertaining, and we chatted for about an hour.

Unexpected Invitation

Then, out of the blue, she said “You’re funny”, and invited me to join her family for Christmas Day! (It was November)

With a fixed grin, I politely declined, saying I wouldn't want to impose.

Inside, my mind was reeling—who asks a complete stranger, who you’ve just met, to a family Christmas? The klaxon was blaring in my head, yet, not wanting to end what was an entertaining meeting, I chose to ignore my concerns and instead suggested we grab some food. So, we decamped and drove to a local restaurant.

We spent about five hours together in all, and despite my initial shock, I found her engaging company.

Anyone who has stumbled out of an unhappy long-term relationship will immediately understand the attraction of being in company that seems to find you interesting.

I’d also mentioned an engineering project I was working on for fun, and she chipped in, “My father has a metal lathe”—random, but guaranteed to interest me! We parted company with a peck on the cheek; however, as I drove home, her Christmas invitation lingered in my mind, nagging persistently and refusing to be ignored.

Concerns and Ambivalence

The next morning, these doubts had in no way dissipated, so I called my friend D again for advice. He'd been divorced and remarried, so I assumed he knew more than me. (This proved to be wrong, but at the point of calling, I didn't know this.)

I ran through the date for him, and true to form, he laughed. I took that feedback in my stride but told him I was pretty ambivalent about a second date. His tone turned serious, and he said, "You have to ignore that feeling, mate. It’s just nerves! You are out of practice, and you probably just need to get laid! Push past that and ask her out again."

It will tell you how out to sea I was feeling because I ignored all of my misgivings and dutifully followed his advice. These misgivings were high: her profile wasn't accurate; she had thrown in a love of aviation after I'd told her it was a passion for me; she'd invited me to a family Christmas—not just a party—after we'd only just met. This made me question her judgment. I recognised I'd been starved of positive attention, and this made me wonder if my "radar" was off.

Despite all this, I called the lady in question to arrange a second date. Also, thinking back to my female friends’ comments about being like a newborn foal in a forest (full of predators), I suppose I wanted to prove everyone wrong.

I’d clearly forgotten that age-old advice: ‘Pride comes before a fall.’

The Second Date: Part One

About mid-afternoon, I collected her from her home, and we drove to the beach, accompanied by her little dog. I say dog, but to me, used to hounds I could wrestle with or go yomping through the forest, hers appeared to be a cross between a Chihuahua (with bulging eyes) and a small rodent.

In fact, as she climbed into the car, he was snugly settled inside her handbag!

I was mesmerised. I’d never seen anything like this in real life. I had to suppress all the comments fighting to come out of my mouth and drive to the beach.

We parked up and set off walking along the seafront towards a café, perhaps about a mile distant.

About halfway there, the dog went for a poo on the beach… it happens.

However, she ignored it and carried on walking; I was stunned!

I stopped walking and pointed out we would need to clear that up. She said she didn’t have any poo-bags and went to carry on walking.

Quite shocked, I went over the mess and carefully dug a hole with the toe of my boot before kicking lots of sand over the offending article and burying it as well as I could.

I almost called a halt at that point, but good manners overpowered my hesitation. I didn’t want to ruin the outing, and I wanted to see how a second date went. We pushed on to the café.

Once there, we sat opposite each other, her pet on her lap. The conversation was easy, and my concerns began to fade. She was witty and entertaining, and although I wasn’t feeling it in the desire department, I was having a good time.

She chose to order the same dish as me, so two plates of smashed avocado on sourdough with poached eggs duly arrived.

As we began to eat, and I raised the first forkful to my mouth, my eyes fixed onto a horrifying scene playing out in front of me.

Her dog put its paws on the table and licked her food. I exclaimed and told her what was happening, and to my surprise, she waved it off, saying, “We always share my food!”

I felt my gag reflex kick in. I’d only ever been around dogs who were valued but understood their place in the pecking order. Dogs, after all, are pack animals, and if poorly trained, can cause all sorts of problems.

The Klaxon was sounding in my head once again!

Second Date: Part Two

My innate politeness kicked back in—keeping my mouth firmly closed.

By way of explanation, I’d spent nearly seven years as a child in an all-male environment of a British Public School.

Back when I attended, the only exposure we had to women were two teachers: one for Maths and one for French. Respect for women was drummed into us—not really as equals, but more in the style of being placed on a pedestal.

Although many years had passed, and I’d had a number of girlfriends before marriage, those relationships were very traditional in terms of the roles we played. I’d also come from a single-parent family, so I had a lot of respect for the sacrifices my mother had made to raise me.

As a result, I felt uncomfortable challenging poor behaviour from women, in a way that did not reflect my comfort in directly calling out poor behaviour from men.

Additionally, having been raised in a male-only environment, I still couldn’t quite believe that some women could be as duplicitous and manipulative as the worst male narcissist.

By the time we’d walked back to the car, and I drove her home, it was beginning to get a little darker. She invited me in for a cup of tea and that cursed politleness kicked in again. I didn’t want to make her feel uncomfortable so I said “Sure.”

As we entered her lounge she pointed out her curtains were drawn and said, "Oh, my mum must've done that."

I found it odd that a 40-year-old’s mother was ‘popping by’ to do such a thing but again, said nothing.

I took a seat on one of the sofa’s and tried to quickly drink my super-heated tea, it took some time.

We were chatting about banalities when she stood up, crossed the room and sat right next to me, well inside of my comfort zone! Next, she placed her hand on my thigh, a little too far up for me to mistake the gesture.

‘Bollocks!’, I should never have come in!

Internally I froze, although you’d never have known. Feeling somewhat obligated, I placed my hand on her leg only to hear a growl from across the room!

The handbag dog leapt off the other sofa and rushed over to dive between us. He snapped at my hand so I lifted it, barely restraining myself from releasing a well aimed back hander!

She made cooing noises, laughed and told me not to worry'. She’d had his canine teeth removed at the vet so he could really do no damage!!

Worse was to come.

The Giraffe Toy

Internal horror mounted as she got up and found the dog a small stuffed animal toy, a giraffe. Clearly, this was meant as a distraction for him. However, it transpired it was more of a horror show for me.

The next hour turned into a surreal spectacle. The tiny, bug-eyed dog launched itself onto the toy with an unsettling enthusiasm, humping it with fervour, all whilst growling in time with each thrust. I sat there, horrified, unable to tear my eyes away from the bizarre scene unfolding before me.

Every so often, it would pause, panting heavily, and shoot me an angry glance, as if blaming me for its indignity. The sight of the frenzied, determined little creature, combined with its accusatory looks, made for an absurdly grotesque tableau. It was like watching a bizarre, low-budget performance art piece, with the dog playing the lead role in a tragicomedy of its own making.

As this was happening, my date became more amorous and kept pushing her tongue into my mouth. I wanted the whole experience to stop but seemed to have lost my ability to protest. It seems inane now, but I didn’t want to offend her. My mind was racing, struggling to process the absurdity of the situation while simultaneously trying to figure out a polite way to extricate myself.

Clearly, she felt no such qualms towards me, and I felt like I was a participant in some low-budget Woody Allen quasi-comedy! The surreal juxtaposition of the humping dog and her aggressive advances made me feel like I was trapped in a bad joke with no punchline.

Eventually, the dog, spent, dozed off and she detached herself from my face to visit the loo. I took a deep breath, momentarily relieved, but my respite was short-lived.

I considered making a break for it, but she was just too fast for me (how was it possible for a woman to pee that quickly!) She grabbed my hand and drew me into the kitchen, suggesting a snack.

The thought of dashing out the door and leaving this bizarre scene behind, was almost overpowering, yet I remained, paralysed by the absurdity of it all.

The Night

She made something light to eat and opened a bottle of Prosecco. I toyed with a glass whilst she had three. All I could think about was getting back to the sanctuary of my own home, and I needed to be sober to drive there.

I pushed back my chair to stand and she stood with me, telling me she didn’t want to be alone. Damn, I didn’t want to be there but now felt a little sorry for her. She asked me to stay the night, explicitly stating we wouldn't be having sex. I was in no way disappointed but was caught off guard by her directness. I protested that I didn’t have a toothbrush, but of course, it turned out she had a spare!

Heading upstairs, I stripped down to my underwear, and she reappeared from the bathroom in a full set of cotton pyjamas. She pointed to the bed—an unspoken command—and I climbed in. She joined me and shuffled back until I was the big spoon.

Inside my head, I was cursing myself for ending up in this situation. It’s not like there hadn’t been any warning signs:

• All the oddities of our first date

• The dog poo incident

• The shared food incident

• The mother visiting daily to close the curtains

• The tooth extraction story

• The sexually abused giraffe toy

Reflecting on the situation, I realised I’d ignored every red flag. Her directness in asking me to stay the night had caught me off guard. I wasn’t used to such bluntness, and it threw me. Yet here I was, spooning a woman I barely knew, cursing my pathetic inability to extract myself from the situation gracefully.

Escape and Evasion …

Ten minutes later, she dozed off. I lay there like a deer caught in headlights, listening to her snores. Thirty minutes later, I realised I had to go. Awkwardly extracting my arm took about five minutes, as she stirred twice. Each time, I froze, heart pounding, praying she wouldn't wake up. Finally, free, I slid out of bed, tiptoed to the bedroom door, to made good my escape.

The narrow staircase creaked with every step. I held my breath, moving as lightly as possible, wincing at each sound. At the bottom, I dressed quickly by the front door, then painstakingly opened it to avoid any noise. I pulled it closed as quietly as possible, then walked lightly to the car and drifted out of the cul-de-sac, feeling like I'd successfully executed a covert operation.

The drive home felt like waking from a nightmare. I laughed with a giddy sense of euphoria and practically skipped up the stairs to my apartment. Just as I was relaxing with a cup of tea, my phone rang. It was her. I hesitated, playing out multiple scenarios in my head, but eventually answered.

"You left!" she accused.

I bumbled out some half-assed explanation that I didn't want to disturb her peaceful sleep and that I had an early start. Her abruptness was jarring, but I maintained my polite facade, ending the call as quickly as possible.

Reflections

Talking the next day with my friend D, I recounted my experiences to his incessant laughter.

“Well, I’m glad you find it so funny, it was a bloody nightmare!” I complained.

I confessed I didn't want a third date and wasn't sure I was ever going to be ready for the dating pool, as it seemed to be full of sharks and my water wings were proving to be utterly useless!

He listened patiently before saying, "Trust me, you really do have to push past that feeling Mark. No-one enjoys it, you just need to find your rhythm; have one more date and see what happens!”

My logical brain was telling me this sounded like a terrible idea; however, as I say, at the time I hadn’t yet reached the point where I trusted my emotions and decision making, especially not where dating was concerned.

So, against all evidence and my hefty misgivings, I agreed with D that I would have another date with this girl, to see what happened.

After all, navigating the dating world successfully takes practice.

Like any skill, if you don’t use it, you get rusty.

So, much like Bambi, traipsing through a tiger infested forest, I listened to my friend’s shockingly poor advice and decided to persevere!

Episode three of this misadventure continues next week.

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… to be continued …