Online Dating Disasters for Midlife Singles: Avoiding First Date Blunders

Dating in One's Middle Years #6

The Absurdity of First Meetings: When Common Decency Takes a Backseat

Why Read On?

Before we wade into the murky waters of midlife online dating, here’s a light-hearted warning: Abandon hope all ye who enter here! If you’re stepping into the realm of first dates expecting a smooth journey, prepare for a few bumps - and hopefully a few chuckles - along the way.

This isn’t just a tale of romantic mishaps; it’s a reminder that, behind the algorithms and curated profiles, we’re dealing with real, imperfect people. And sometimes, in the rush to find "The One," basic social graces get tossed aside, turning first meetings into perplexing encounters that leave us questioning the whole process.

Today, we’re diving into the bizarre world of first dates, especially those spawned by online dating.

What is it about this digital approach that leads people to abandon the most basic social norms?

In the frantic quest to find a connection, common courtesy often falls by the wayside, leading to encounters that are as - awkward - as they are memorable. I'll share three personal stories that highlight these absurdities and reflect on how this hurried approach can drive away anyone with a bit of self-respect.

The Property Portfolio Surprise

Her profile was impressive - a radiant smile, witty text banter, and a confident aura that was impossible to resist. We arranged to meet at a busy chain coffee shop. As she walked in, I was relieved to see that she looked just like her profile - fantastic. We exchanged pleasantries, and after a brief moment of small talk, I went to order the coffees.

As I returned to the table, she looked up and, with the casualness of discussing the weather, asked:

"So, how many properties do you own?"

For a moment, I was completely taken aback. ‘Did I mishear that?’ I thought, as my mind tried to catch up with the unexpected question. It felt like I’d suddenly been dropped into a speed-dating event where the next logical question would be about my credit score. I forced a smile, stalling for time. “I’m sorry, what?”

She didn’t miss a beat. “How many properties do you own?” she repeated, as if this was the most natural way to kick off a first meeting.

‘Is this really happening?’ I wondered, internally cringing at the abruptness. I managed to gather my thoughts and responded, “That’s an interesting question. Why do you ask?”

She sighed, launching into a story about a past relationship with a violent freeloader who had taken advantage of her financially. As she talked, I nodded sympathetically at the appropriate moments, but my mind was racing.

‘This is where we’re starting?’ I couldn’t shake the discomfort.

Once she finished, I gently asked, “Do you think it’s appropriate to start a conversation this way?”

She looked genuinely puzzled. “Well, I just want to make sure I don’t end up in the same situation again.”

I offered her a polite smile and said, “I’m sorry to hear you’ve been in that situation; it sounds difficult. But it wasn’t me who did that, and I can already tell we’re not suited, so I won’t waste your time. I wish you well.”

The confusion in her eyes told me everything I needed to know. I got up, left her to her coffee and, presumably, her property portfolio checklist. As I walked away, I couldn’t help but reflect, When did common decency get replaced with such blunt pragmatism?

The Marriage Ultimatum

About a month later, another striking profile caught my eye - beautiful, with a warm smile and a stated desire for "the big romance." The vague allure of her profile intrigued me, so we agreed to meet. We exchanged pleasantries, and as we stood in the queue, we chatted light-heartedly about favourite coffees and films. But as soon as we sat down, she leaned in, her expression turning serious, and asked, “Can I ask you a personal question?”

Every man knows this is a minefield. With a sinking feeling, I nodded, bracing myself.

“Do you see yourself getting married again?”

The shock must have been evident on my face as I blurted out, “To you? We’ve just met!”

Realising how blunt that sounded, I quickly tried to craft a more considered response. I stalled for a moment, then said, “I’m recently divorced, so I’m not really in the emotional place for marriage just yet. Maybe, with the right person, someday... but not now.”

Her face fell instantly. “Oh,” she replied, her voice tinged with disappointment. “Well, I want to get married.”

She spoke for a few minutes about love, but to my more sceptical ear, it sounded like she was more focused on financial security.

The atmosphere shifted noticeably, the once-easy conversation now heavy with unmet expectations. I took a deep breath and said, “I can see you know what you want, and that’s admirable. But I don’t think we’re looking for the same thing right now. I wish you all the best.”

Her expression softened slightly, but the disappointment lingered. As we parted ways, I couldn’t help but reflect on how the pressure to define our futures in the first moments of meeting can snuff out any potential for connection - like a firework that never quite ignites.

The No-Filter Approach

This last encounter still leaves me scratching my head. She was well-educated, well-travelled, and seemed to tick all the right boxes. We met for a drink, and after a few polite exchanges, she dropped a bombshell: “I don’t date men who earn less than six figures.”

Her bluntness wasn’t the issue - it was the sheer lack of tact, the presumption that financial worth was the sole measure of a person’s value. She didn’t even know my last name, yet she felt it appropriate to inquire about my income bracket.

I managed a faint smile before excusing myself from the date that never really began. As I walked away, I couldn’t help but ponder the state of modern dating, where such a materialistic mindset seems to have replaced the more subtle art of getting to know someone.

Conclusion: The Rush to Judgment

These anecdotes reveal a troubling trend in the online dating world, where the rush to filter out the 'wrong ones' often leads to a disregard for basic human decency.

It’s understandable to want to avoid emotional exhaustion - online dating can be draining - but this rapid-fire approach almost guarantees you’ll sabotage any chance of genuine connection before it even begins.

If you find yourself too drained to be civil, it’s crucial to recognise that and take a break, after all:

• Pilots don’t fly tired

• Drivers are advised to rest to avoid accidents.

Dating should come with the same caveat - when our loneliness pushes us to rush, we dramatically increase the likelihood of things going wrong.

Rather than shielding themselves, these women were unwittingly ensuring that anyone with a shred of intelligence and self-respect would walk away.

This behaviour, driven by the efficiency-over-empathy nature of online dating, is ultimately self-defeating.

It repels quality individuals who value more than just a checklist.

If only we could revive the art of conversation - remembering that it isn’t dead, just neglected - perhaps first meetings would feel less like the job interview from hell.

You show up hoping to meet someone likeable, with shared values and a spark of connection, but instead, you often find yourself sitting across from an interviewer armed with a list of rigid requirements.

You’re grilled about your qualifications for a role you’re not even sure you want, with no idea if the company - your date - is a place you’d want to work for, let alone spend your future with.

Of course, this isn’t a problem if you’re simply looking for a “casual distraction,” but if that’s your goal, at least be honest with yourself - and perhaps even the other party!

But all is not lost. By applying a few simple strategies, you can avoid these common pitfalls and create a more fulfilling dating experience that prioritises genuine connection:

Top 3 Tips to Avoid First Date Blunders for Midlife Singles

1. Pace the Conversation—Don’t Rush to the Deep End

• Why: Jumping into heavy topics like finances or marriage right at the start can be off-putting and will kill any potential connection before it even begins. A first date should be about getting to know each other in a relaxed and enjoyable way, not an interrogation.

• Tip: Focus on light, engaging topics that allow for mutual discovery. Ask open-ended questions that encourage conversation rather than putting the other person on the spot. Save deeper, more personal questions for later dates when there’s a foundation of trust.

2. Prioritise Respect and Courtesy

• Why: The lack of basic social norms, such as tactfulness and empathy, can turn a promising date into a disaster. Remember, you’re dealing with another human being, not just a profile on a screen.

• Tip: Treat your date with the same respect and courtesy you’d expect. Listen actively, show genuine interest in their answers, and avoid making the conversation solely about yourself or your needs. A little politeness goes a long way in leaving a positive impression.

3. Be Honest but Tactful

• Why: While honesty is crucial, the way you deliver your truth matters. Blunt statements about financial expectations or marital intentions can come across as harsh or transactional, rather than genuine.

• Tip: Frame your honesty in a way that’s considerate of the other person’s feelings. For example, if financial stability is important to you, discuss it in the context of your long-term goals rather than as a dealbreaker. This way, your values are clear without making the other person feel judged.

These suggestions aim to foster better connections and more enjoyable first dates by encouraging thoughtful conversation, mutual respect, and considerate honesty.

If you’ve enjoyed this story, make sure to subscribe for more updates. Next week, I’ll share another example of 'Mid-life Dating' where, even by my standards, I was shocked by the behaviour! Click here to follow along with my previous misadventures.

Have you experienced any midlife dating disasters? Or do you have your own tips to share? Drop a comment below - I’d love to hear your stories and advice!

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