Can I let go of my hangups and date a small man?

Apart from the late night I mistakenly slathered HRT gel across my face thinking it was night-time serum, which resulted in what looked to be scarlet fever, last week I endured my most mortifying moment of midlife. Last week, I broke a cardinal sin like no other. Last week, I sabotaged the number one rule of female friendship. Last week, I went on a date with the same man a close friend was already dating. How was I supposed to know we were talking about the same “Henry from Hinge”?

A man named Henry – a warning sign if ever there was one – is apparently pretty active on Hinge, the dating app where middle-aged cast-offs “hang” in the hope of finding love for the second, third, fourth time. Clearly on the hunt for several wives, a few weeks ago Henry “liked” my photo and, after a cursory glance at his profile, I agreed to “match”, meaning we were free to strike up a chat on the app.

Henry is way shorter than the men I usually go for (I tend to draw the line at 5ft 9in), but given I’m not having much luck dating-wise, I decided to let go of any preconceived ideas about small men and give the vertically diddley dude a whirl. Who needs to struggle in vertiginous heels anyway? The banter (hate that word!) flew back and forth and inevitably one of us suggested we move our chit-chat over to WhatsApp, which in the online dating world is the ultimate act of commitment. Clearly clever, own teeth, a full-time job, two kids, own hair, I think – although he seemed to be wearing an awful lot of hats in his photos – I immediately assumed this one had legs (hopefully two, but honestly, one leg or two… it really doesn’t bother me at this point). Determined not to build a false impression from his photos (AKA a fantasy made up in my own mind), despite the beanies, I committed to a date.

Based on a couple of microscopic details “spotted” in photographs, it’s easy to conjure up a totally incorrect picture of someone. Show me a dating profile photo and I’m a sleuth on a mission with a magnifying glass, poring over every single detail. I’m not alone. Even the most mild-mannered woman can be easily persuaded into a little “forensic detective work”, so believe me when I tell you many women I know screenshot profiles pictures and, forefinger and thumb at the ready, zoom-in for a really good nose. I’ve discarded many a potential ‘“match”, thanks to spotting, say, a dead potted plant in the bottom right-hand corner of a photo.

Dead houseplants can surely mean only one thing: axe murderer. No photos or pictures on walls equals he must be on the run. Bad blinds in the bedroom could very well result in a poor night’s sleep (for me) at some stage in the future, so nope, I “unmatch” immediately or don’t bother “matching” at all. As for bathroom shots – “ho ho ho come to mama” – it’s amazing what you can discover about a person with a quick zoom, a steady hand and an iPhone backlight set to full beam as you hover over an image of their bathroom shelf. Admittedly, in the past my sleuth tactics haven’t always gone to plan. There was the time I spotted the corner of a yellow Selfridges bag and assumed my date would turn up well-dressed in a modern, contemporary way. In the event, he strode into a central London pub in green Hunter wellies – I mean, it wasn’t even raining. There are always exceptions to the rule, of course, but generally speaking, if a person uploads an image from home, there’s an awful lot to discover about them with a little patience.

Who knew Henry’s architecturally tasteful interiors housed a right old lothario? Working for a hipster-sounding tech start-up, Henry booked a restaurant in Peckham (keep up, dears – it’s the new Shoreditch). He arrived on a skateboard but, you know, didn’t look too ridiculous, on account of, um, being the size of a 10-year-old. Proof you should never write anyone off, we got on really well and a second date was arranged (and yes, he paid the bill in full – see last week’s column for my thoughts on that).

For the second date, I chose a bar in west London, mainly because second dates weird me out – what if I don’t like them enough for a third? – so I like to be closer to home. As it turns out, there was absolutely no need to worry about another date: on my way home in an Uber, Henry messaged, “That was so lovely! See you again for a third?” Before I could hit reply, a second missive appeared along with a photograph. “Forgot to mention, I found your red-haired doppelganger!” Staring at an image of myself wearing large sunglasses and a hat, seated next to a good girlfriend, for a moment I couldn’t figure it out. Then I realised it must be a screenshot of my friend’s dating profile on Hinge, a picture taken of us on a recent holiday, which meant he must have been in touch with Katie. “That’s not a doppelganger,” I replied, “that’s me with Katie, she’s a close friend.” To avoid further awkwardness, I flicked my iPhone to “Do not disturb”and called Katie to break the news and also, given nothing had happened between us, to tell her she “could have him”. After a pause to gain recovery, she spat, “Ugh, I don’t want him.”

Several months into single life, each week throws up something unexpected. Just as you master how to move conversations from dating app to WhatsApp, just as you work out how to arrange a first date and how to decline a second, just as you think this “dating in mid-life” stuff couldn’t get more complicated, you find yourself dating the same men as your mates, and questioning the idea of ever finding a meaningful relationship online.

It feels like a bit of a free-for-all out there in the online ether, as if no one’s really taking it very seriously. Call me old-fashioned, but I thought third-date territory was supposed to be reserved for people you’re invested in. Apparently not. I’m not sure I’ll ever master the art of dating in midlife, but if there’s a handbook available, could someone please mail a copy to the Telegraph offices?

Since Henry, three girlfriends and I have a new approach: we screenshot the dating profile pictures of the men we are talking to, to ensure we don’t have a crossover, and share over WhatsApp. And as it turns out, there are multiple crossovers, similar conversations being had and – wait for it – identical restaurants being suggested, not to mention a few dead pot plants scattered here and there. Speaking of axe murderers, I’ve added “Immaculate American Psycho-style interiors” to my red-flag list. Sorry, Henry, you’ve clearly lost your head.

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