Unpicking the rules of modern dating can be tough, especially if you're late to the game. This 50-year-old divorcee went out on date with a 43-year-old woman a few years back. She was lovely – slim, pretty, clever, sexy, successful – but frank, terse and abrupt to the point of rudeness. For instance, before she agreed to meet IRL (we made first contact online) she emailed a load of questions. Did I have a job? Did I own my home? Did I have a car. Yes. Yes. Yes.

OK, now send a recent photo, preferably with your face next to today’s newspaper so I can see that it’s a true image of you now, she demanded, apparently concerned that tonsorial, dental and corporeal conditions etc might have deteriorated. What? Like in the movies, when a kidnapper is demanding a ransom? Yep. OK. Weird. But I comply. And I pass the test.

A few days later, approval now registered and processed, drinks, dinner, more drinks. During the coffee course she moves from her chair to my banquette and leans in to kiss me. Quite passionately. On the mouth. On our first date! Once in the taxi, on her way home, she follows up with a volley of text messages. She is very very keen. She says she wants to come and stay at my place for a weekend. Wow. I am smitten. Then… radio silence. Play it cool, Simon. After three days, a slightly less encouraging missive. “This isn’t going to work. We are not compatible. I want kids. With someone younger than you. And you haven’t watched all seven series of Mad Men. Thanks for dinner.” We both moved on.

I’m telling this, not to engender some kind of pity party, not to beg you to empathise with the sad and lonely plight of the clunky, analogue, single, white, middle-aged man in the modern, hyper-connected digital world, but more to illustrate the sheer speed and velocity that later life love plays out at. Nothing like divorce or death to make one realise how short life is. This is what I have found, anyway.

When you are in your 40s and 50s, all dating is speed dating. It is picky and direct, fast and decisive. The hurtle towards probable decrepitude, mental desiccation and solitary conclusion means that there is little time for kiss chase, negging, and bullsh----ng anymore. Honesty, practicality and brevity are the new seduction. No point in messing around. No need to fib or tell lies about liking “long walks” “jazz” and “the theatre”. Your body is telling you to slow down but in matters of the heart you have to get going. We might only have, say, 10 or 20 years to go. If we’re lucky. So giddy up.

The actress Alice Evans, 50, knows this. Still in the throes of a very public break-up with actor Ioan Gruffudd earlier this year, Evans is already auditioning for husband number two. “I just want a nice chap who is a raging Democrat… likes to talk and talk and talk about anything (interest in fashion, foreign languages and civil aviation would obviously help).” As Alice’s dating coach, I’d also have to suggest pragmatism.

At a certain age, when one is back “out there” (Carrie Fisher in When Harry Met Sally) or looking to “re-partner”, the four Ls of Location and Logistics have to be considered along with Likeability and Libido (believe me, you are too old for a long-distance relationship). Boring stuff like mortgages, property, ex-husband access and school schedules also come into play. (If she has kids, teenagers should be preferred. They take up less time, are less demanding financially, emotionally and temporally and will be out of the house/picture sooner.) Sounds a bit cold, right? But lasting romance will happen, if you’re lucky, when all this stuff is agreed and sorted.

Newly separated UK politician Michael Gove, aged 54, is taking a somewhat different approach, raving his nicely ironed Charles Tyrwhitt shirt off at 1.15am in the Bohemia nightclub in Aberdeen the other night. “I love dancing!” Gove is reported to have said to his bewildered (and millennial) fellow party-goers at the Aberdeen boîte that night, before throwing 1990s Dad shapes on the floor until the early hours.

“Dancing”, my foot. Truth be told, having just split from his wife of 20 years, the journalist Sarah Vine, and now facing up to life as a single man with fewer responsibilities and more free time, the Tory minister was probably, very likely, out on the pull, on the hunt for the next Mrs Gove. Or whatever. (On his Bumble dating biog, btw, Gove describes himself as a Virgo who “works out sometimes”, a “conservative” and “not sure what he’s looking for”.)

Oh dear. Is there anything more downright tragic than a 50-something old man at a young people’s disco trying to keep up/get down with the kids? It’s even worse if he’s trying to get off with one of them in between frugs.

I know this because seven or so years ago, as a 49-year-old, freshly divorced man myself, I also played the starring role in my own massively messy, highly regrettable, late-night Gove story on one or two occasions. It wasn’t funny or clever. No man approaching his leisurewear and free bus pass years wants to be thought of as the kind of berk who chases age-inappropriate girls in places with a Sports Direct dress code and squash-nosed bouncers in the loos. And no man past 40, unless his name happens to be “Hefner” or “Stringfellow”, wants to be with the kind of women who might frequent that sort of establishment either.

One can also sympathise. Dating, you thought, like red Kickers, skateboarding and acne, is something that should only have to be dealt with in one’s youth. But you get married, have kids and go through a divorce, and suddenly you are where you never thought you would be. Fifty years old. Single. WTF? Back when fellas like Gove and me were last single. Before smartphones, festivals and Tinder, clubs were where we used to find girls. So if not the bar, the VIP area or the dance floor, where?

Dinner parties? You get invited to a flurry of these when your single status is still regarded as a novelty by your immediate social group. You’ll be fixed up and matched via tactical placement or strategic invitation. It’s sometimes lovely. Mostly it’s awkward. Dating my ex-wife’s girlfriends and even our wider circle was uncomfortable. Stuff gets back. Divorce makes for toxic and bitchy gossip. Stories are told. Most of them about you. None of them good for anyone’s reputation.

So, you are on your own: drinks parties and BBQs (host your own), garden fetes, art galleries, book shops, hikes, museums, antique markets. The gym? Bit sleazy. Hotel bars are just about OK, if you are abroad.

Dark maybe, but funerals are also a very lively possibility – a pretty, 50-year-old, sadly widowed friend of mine said she received two proposals for dates from her dead husband’s friends at her husband’s wake. Best advice? Get a dog. Walk it every day. You’ll meet dozens of women every week.

Really, cyberdating is where it’s at for older, sensible and pragmatic male realists who don’t have the time or inclination to wander aimlessly up and down the aisles of the love supermarket. Be careful to choose a service that caters for one’s specific age group – I know of one divorced dad who got swiping on Tinder only to discover his teenage daughter’s profile staring at him. Before you try, be aware that it is brutally Darwinian environment, where love is won and lost in seconds, at the click of a mouse, at the conveyance of a text message (get ready to be ghosted, ignored, stood up)… and that is an absolute godsend for the middle-aged and divorced, offering older people a genuine chance at a second life. Yes, I really did just say that.

You need to get good at dating again, recalibrating and updating your technique for an altered landscape of acceptability. I was told to employ canny levels of humanistic neuro-linguistic psychology, not to show off, to listen to both my own conscience and to what she is saying. Acknowledge my own needs and respect hers. Be honest about what I wanted, and don’t talk about my ex-wife.

Ditch the smarm and clever lines, too. One thing I noticed during my two years of middle-aged dating was the declassification/rebranding of “charm”. Modern women are suspicious of and largely resilient to it: the sobriquet “charmer” is now a pejorative and loaded compliment, bestowed often on men (and rarely assigned to women) and only a few removes from “bounder”. Dinner or drinks may be too intense and transactional for a 21st century mindset, so try suggesting a walk or an exhibition, anything where money is not handed over. (On a Sunday afternoon park date, you’ll also discover if she really does like “long walks”.)

Many of the middle-aged women you will meet will be embittered by divorce, harbouring a profound mistrust of men. They have been two-timed, cheated on and humiliated – so you have to offer a genuinely convincing alternative. That said: keep it light, avoid questions that sound like a job interview grilling. “Where do you live exactly?” “Why are you here?” “What do you do?” “What do you like doing in your spare time? Etc. I found that women responded best to impulsiveness and spontaneity, a simple and direct attitude, a person who is willing to take a chance. A man who flirts, makes eye contact, who will risk a kiss.

Don’t always expect to be in control. During my second single-life experience, I met a delightful 45-year-old ex-model, a single mum with a degree, a winning personality and a thing for champagne. She’d recently come out of a long marriage to a semi-famous actor and appeared keen and organised. When we arranged dinner, she suggested the date, time and venue. (With rather too much brio and efficiency, I think.) We met. We got drunk together. Playfully, I bragged about the amount of “likes” I had already accrued – more than 20! – on my dating app. She looked unimpressed. “I have over a thousand,’ she said, flatly.

I was, it transpires, her 60th or so internet date. Most of them at this very table, at this bar, close to her home, hence the efficient arrangement. She was, she explains, trying for 100 dates. Perhaps to write a book on the subject. After our dinner, my follow-up text messages went unanswered. Audrey has since remarried. I am considering a ring and an engagement. Love moves at 100mph when you are 50.

© Simon Mills / Telegraph Media Group Limited 2021
This story originally appeared in the Telegraph and is reproduced with permission.