Over 60 Dating Tips & Advice

I first dived into the murky waters of internet dating in 2024, not long after my 60th birthday. Crazy time to start sowing wild oats, eh? But I had recently split up with my long-term partner and friends persuaded me that 'everyone was doing it'. Besides, being all sad and lonely was becoming a drag. So I embarked on a year (well, more like 18 months) of 'dating dangerously', as chronicled in the memoir I wrote about it. I've been a journalist all my life so it seemed natural to record my experiences.

Back then, the dating sites I signed up on (not to mention the then-novel Dating app) were full of young men looking for 'action', if you get my meaning, and to my amazement they weren't put off by my age. On the contrary, for many of them it was virtually an aphrodisiac. I suppose young men have always fantasised about older women. And for a while this was all harmless, carefree fun. I had my escapades, some exciting, others I could have done without.

But the thing about young men, especially in today's digital world, where all arrangements are subject to change and attention spans are miniscule, is that they are infuriatingly unreliable. So, call me old-fashioned, but in the end I simply got fed up with the flighty behaviour. I met men in their mid to late thirties who still behaved like teenagers, just after some no-responsibility fun, even though they were creeping towards middle age. In any previous generation, most men of that age would already be married and have started a family. But this lot had been infantilised by decades of playing on their Nintendos and PlayStations and Xboxes and didn't want to grow up. And perhaps the high incidence of divorce in their parents' generation (guilty, M'lud!) also made them shy away from serious commitment.

Cosmopolitan dating

I decided to give my contemporaries more of a look-in and found that the middle-aged (and older) have taken to this virtual world with a vengeance. Where else are the legions of divorced, separated and widowed oldies to go, now that they are footloose and fancy-free and still in the market for meeting people? I also discovered that an internet dating site can be a real microcosm of our society: I met doctors and documentary film-makers, City financiers and retired dons, in the same pack of cards as construction workers, painter-decorators and cabbies. And talk about cosmopolitan! In the same month I dated a Spaniard, a Greek, a Dane and an Italian, in addition to the pub-joke routine 'Scotsman, Irishman and Englishman'. The common factor which united them all was the search for a mate – whether short term or long term - for bedroom high jinks or romance or companionship.

The oldest fella to message me was an 80-year-old widower. He seemed nice and good-natured and was clearly game to meet new ladies to help take his life forward. But he looked every bit his age and I wondered, a little sadly, which woman of my younger vintage would choose the elderly, frail gent to paint the town red with. I mean, his name wasn't Getty.

Moving down a notch, I gasped when I spotted online the dating profile of a family friend, a long-married man and paterfamilias with a horde of offspring, as well as several grandchildren. He was 75. Grey locks flowing, a naughty smile playing on his lips, he announced that he was 'up for anything'. Who knew? Not his wife, that's for sure.

Who to meet and who to delete

Reflecting society as a whole, dating sites do have their saddos and weirdos, kinky types, poseurs and cheats, the idiotic and the merely dull. I have matched with a few charming and thoroughly decent men, and had some enjoyable dates. I eventually got more proficient at choosing who to meet and who to delete. But even so, I sometimes found myself in an utter mismatch. For example, there was Ted. Aged 37, intelligent, professional, presentable, nice manners. We exchanged messages in the build-up to a meeting. He said he loved cooking and sent me photos of dishes he had concocted - various platefuls of colourful mushy stuff. Vegan, he explained. He'd already told me he was teetotal. And when I mentioned that I was watching a cop show on TV, he said he didn't own a television and only watched vegan cookery demonstrations on YouTube. Well. I am a meat-eating, alcohol-drinking telly-watcher. 'Ted', I said, 'this is never going to work!' Then came the killer rejoinder: 'Would it make things worse if I told you I lived with my mum?'
Oh, Ted.

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My Over 60s Dating Top Tips

1. As a mature adult you'll need to employ all the healthy scepticism you've built up over the decades, because it's easy on the internet for a person to lie about who they are, what they look like and what they are after. Some purport to be single, while having a hapless spouse at home And even the well-meaning can be so dazzled by the smorgasbord of dating options that plans and arrangements are all subject to change without notice. So believe in nothing until it happens, and take no one at face value.
2. Don't leave yourself emotionally vulnerable by investing too much hope in a particular potential mate, or after sharing physical intimacy with someone. If you meet someone you fancy and you are both up for it, by all means enjoy the sex, but - and this isn't always easy, especially for women - take the emotion out of it or you will leave yourself open to being hurt. If and when a deeper relationship comes along, your emotions will come flooding back.
3. We've all heard those woeful stories of online dating scams, so don't fall for one. The vulnerable, lonely women preyed on by men who promise them love before persuading them to hand over their life savings for phony hard-luck scenario. And the glamorous young foreign women who manipulate an older man's vanity as an easy way into his wallet. If it all sounds too wonderful to be true, that's because it's a lie. Never give money to a stranger whispering sweet nothings into your computer.
4. Be friendly but on your guard. Don't provide intimate details about yourself – address, phone numbers, social media accounts, even your surname - until you feel comfortable with the person you are dealing with. Keep your communications via the dating site, where there is supervision, and tell the site administrator of any concerns you have.
5. This is an obvious one, but merits repeating. When you do progress to a 'real world' date, do it somewhere public, neutral and busy. I didn't always follow this advice and now realise that if I didn't come unstuck it was more to do with good luck than good sense. There is a reason why my memoir is called My Year of Dating Dangerously. Be smart.

Despite its frustrations and disappointments, I loved my adventurous year of internet dating. I met a staggering array of people, had some good times, and learnt a lot – about myself and life. It is a world of opportunity. Delve in. And good luck.