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Midlife Online Dating: the Good, the Bad and the Ugly
Photography by NOAA on Unsplash

February 2024 – By The Secret Online Dater

Theme: Relationships

Midlife Online Dating:
the Good, the Bad and the Ugly

In this candid account for This Curious Life,  our intrepid mystery online dater takes on the adventure of exploring dating sites tailored for the’ over-50s’. From seductive marketing promises to encounters with a rogues’ gallery of profile pictures, our Secret online dater’s journey unfolds with equal parts disbelief, self-doubt, and laughter. Amidst the chaos of quirky interactions and peculiar profiles, she reflects on the need for a revolution in online dating, supported by insights from our recent survey. Ultimately, her story becomes a call to action for businesses, urging them to prioritise user experience and authenticity in the pursuit of love. 

Pink hearts on a pink background

Photography by Rodion Kutsaiev on Unsplash

So there’s me: right in the middle of marvellous midlife. Mood swings, menopause and mortality – the realisation that death is something that could actually happen to me, not just to old people. Another long term relationship gone South and wondering whether I should hang up my stiletto-heeled boots. Time to grow old gracefully, settle for a male companion to play golf with. 

Yet somehow I’m clinging on to the idea that it must be possible to find a personable, quarter-way decent man before my memory goes and I forget why I might even want one. But wait! Surely everyone, regardless of age, dates online now and there are actual dating sites for the over-50s. 

The marketing is seductive. Who doesn’t want to ‘get someone who gets you’, have their ‘last first date’? The ‘50+’ ads show a charming grey-at-temple gentleman holding hands with a well-groomed lady as they glide around an exhibition of Post-Impressionist art, cartoon hearts forming haloes around their heads. Looks promising, I think, as I put down my vibrator and reach for the credit card. 

After a few weeks of tentative browsing, the initial optimism drains away – the apps are awful, the photos frightening, the interactions inane, insane. Lurching between self-doubt, disbelief and hilarity, I get an overwhelming urge to over-share my experiences. I probably should’ve been a journalist as l love to expose – albeit not in a Naked Attraction way. So I’m appointing myself to the role of mystery shopper for midlife online dating and this is my story. 

* * * 

The Rogues’ Gallery. 


I start by checking out the photos, trying to stay open-minded. Straight men don’t still expect to attract women using a photo of themselves holding a giant fish do they? But behold – here’s Colin clutching his scaley whopper! Other props feature frequently too. I see an 18th century judge complete with curly wig, a muscle-bound youngster brandishing a dangerous looking power tool, a man with a bucket over his head, one waving around a red, phallic sausage and another sitting in a bin-shed with a cigarette dangling out of his mouth. 

When someone tells you who they are…. 

I try to stay positive. Maybe the profile descriptions will help me sift out someone compatible, relatable, funny? Jimmythehorse thinks he is hilarious: “I do love to have a laugh, like being in a toilet somewhere and finding out there isn’t any toilet roll left when it’s too late”. Tahir goes for the romantic approach: “What I don’t like is a lack of interest in frequent physical closeness and uninhibited experimentation”. Robert, age 58 (and no oil-painting) only has one requirement: “a super-attractive lady, under 30, fit, firm and fertile”. 

I haven’t received any dick pics though and I understand that this is de rigueur for younger people (and gay men). Quite ageist really.

Direct and indirect messages. 

An email arrives from the dating site: “You have a message from Getlucky69 that will set your heart a-flutter. Getlucky69 is completely smitten!!”. Full of anticipation, I click on the message. It says: “Hi”. This, if I’m really honest, does not provide a fanny-flutter. Another random dater sends me an introductory greeting: “hello u r beautiful wanna catch-up”? Starting from when, I think, the beginning of my life up to today? I haven’t received any dick pics though and I understand that this is de rigueur for younger people (and gay men). Quite ageist really. 

Occasionally I stumble on a profile that looks vaguely hopeful and I send a chatty opening message. More often than not there’s no reply. Occasionally a conversation gets started: 

Him “what are you doing this weekend” 

Me “oh, just the usual – shopping, seeing friends. How about you?” 

Him “I’d love to be drinking lager in bed with you” 

Usually I’m the one who gets ghosted but this feels quite paranormal and I can’t wait to disappear back into the ether. 

bottle of lager on a bed

Photography by Rashid on Unsplash

* * * 

I’m losing hours of my life and most of my remaining marbles attempting to make a real connection. It’s hard to keep the faith. 

Have I met any nice guys? Yes. In between the creeps, psychopaths, sex pests and scammers there are a few lovely men, some of whom have been shafted or demoralised by past relationships. But the process is painful. And the dating sites are virtually uncontactable for support. Except when they occasionally send me emails like, “You recently messaged Sven. Our moderators have removed his profile. This is nothing to worry about but if you have given him any bank account details we suggest you change your password”. 

A man in a suit with his fingers crossed behind his back.

* * * 

So, what needs to change? 

My generation invented the sexual revolution. Women were told we could have it all and, as we live our longer lives, we still want it all. To be single. To look again (and again) for a satisfying long term relationship. To do something completely outrageous. Society needs to acknowledge and facilitate this. 

Online dating is a multi-million pound market. But check out the TrustPilot reviews. Users are consistently frustrated by poor app design and the quality of the ‘matches’. “Zero customer service and out of date profiles”, “all the women are looking for superman with a BMW”, “the over 50s men look like they’ve just come out of an inbred swamp”. 

Better still, to create new and healthier ways for us all to socialise with real people in real life.

There’s a real business opportunity here for companies to do some proper market research, make the process more user-friendly and less demoralising. Better still, to create new and healthier ways for us all to socialise with real people in real life. 

I’m writing as a midlife woman looking for a midlife man – and things ain’t pretty. I’ve heard from male friends that it’s no easier. Can we hear their stories too and those of the LGBT community to see if their experiences are any better? Society and business need to keep learning. And until things get better, we as individuals have to remain resilient and keep that GSOH (good sense of humour) that we all talk about.