Learning to date, a 50 year old Valentine

Wiping away a tear of laughter, I waited to catch my breathe. Prunella was in full animated flight, telling us her best and worst dating tales at our girlfriends Sunday lunch in Greenwich. She’s petite, beautiful, always well-turned-out, eccentric and has a quick wit and lilting Irish accent. She’s also over 50 and now a veteran of the dating world after her painful, acrimonious divorce a few years back. Her ex-husband went full demon on her after 20 + years of marriage, he’d hidden a whole other personality – oh and a mistress and all their savings. When I say it was bad, I mean it was BAD. Prunes still got her strong spirit and her devoted son and menagerie of dogs, cats and foxes though. She also, eventually, got her home back which is fantastically decorated in her lovely witchy style.

Lou Ellen joined in, she’s only in her mid-30’s but had gone through a similarly heart-breaking marriage around the same time as me. Which had been fortuitous in a sense as we’d supported each other in the way only friends who personally understand the pain and confusion can. Lou had thrown herself straight back into dating without stopping to pass go. Ultimately, this led to her current loved-up state with a good egg and gent, Hugh the naval officer. He’s very kind and helpful with her wee toddler, who can be quite the handful. But before Hugh, there were some characters, some unrequited feelings, some romantic dates and some disastrous dates.

Having lived and learnt, neither Prunella nor Lou Ellen will suffer nonsense. They took enough from their ex-husbands and won’t be tolerating fools again.

Driving Karena and I back home to the coast, I admitted, this has got me thinking, “Am I ready to try dating?” It sounded like a fun adventure.

I’d purposely not considered dating or men full-stop for some time after extracting myself from my ex. I’d felt it was necessary to take time to be on my own – to heal, think, feel, breathe and be peaceful. I’d done all that and was feeling balanced and myself again, I also didn’t want a serious relationship, but I did miss male company. I’ve always worked with men, had men in my friendship circle and after lockdown I wasn’t spending any time around men at all. I missed them. I’m a girl’s girl, regardless of my stealing, lying, cheating ex – I hadn’t gone down the “all men are bastards” road, because it was one person, not an entire gender’s failings. I’ve always liked men and I’m talking in the genuine platonic ‘enjoy your company’ sense, not something equivocal to ‘I’m a nymphomaniac’. Quite the opposite, I didn’t realise it then, but my body had shut down as part of my inner survivalist’s tactics during the bad years (with my ex).

A fun adventure, with stories I could later regale my friends with. What’s not to love! I certainly love fun and adventure – what could go wrong? I’m writing this for anyone else out there, thinking the same, at a non-spring-chicken age. I’m certainly not going to put you off, on the contrary – go for it! I’m simply sharing my experience, not as a guide but just to say – hey, it’s possible to learn new tricks no matter your age or past or whatever.

First, I asked my friends for advice about how to get started in this internet-dating world. When I last dated, it simply involved a few tequila shots, locking eyes with someone fanciable, looking away, flicking your hair and being asked to dance. Ah, the good ole days, drunken snogs in doorways with Haddaway singing ‘What is Love’, on full blast. Now, all done via an app on your smartphone. Not as much fun, but it’s the cultural norm in the 2020’s. It’s kept a lot of people entertained during the lockdown’s – hence the phenomenon of ‘lockdown romance’, most of which were over when lockdown was.

There’s so many though! How do you choose which online dating app is best for you? I read some articles on it and then I asked my friends for advice. I learnt that it’s super important which one you choose as to how successful your experience will be.

I’d started with a plan to only date men in my own age range of 50 something. So, ignoring my friend’s advice, I tried a dating site specifically for this age range. It was ok, I chatted on the messaging service with some ok guys and a particularly keen one on the phone. He seemed nice enough, had a cheeky cockney accent and loved nature and kayaking – tick, tick and tick but when he opened his mouth to smile his teeth looked like he’d smoked 100 rollies a day for several years. Which I think during his early army career, he probably had. Now, I’m not a teeth snob (this is Britain) but clean looking is essential or I’m not going anywhere near there with my own mouth.

On that 50 something site, I did learn – don’t bother responding to people just to be polite, they’ll not always be so back. A chap I wasn’t remotely interested in kept messaging me, I didn’t want to be rude, so I’d half-heartedly messaged something polite back but when he found out I wasn’t a rugby fan – he blocked me! The audacity! I hadn’t wanted to talk to him in the first place, had been nothing but polite and got this extremely rude and overly dramatic response. Lesson 1: don’t talk to anyone you don’t really want to, total waste of your time and there are some right idiots out there.

Then I thought, I’ll try a site that appeals to other people that are interested in the same things, like literature. So, I signed up with a quality newspaper’s dating service that appeals to people who like to read. Their sign up process was great for people like me, you got to write War & Peace for your profile – lamenting on and on about yourself. I really took to that, then sat back and waited for like-minded types to contact me. Some did, but mostly it was like a scene from a western movie; where everybody has moved on and only tumbleweed and dust are rolling down the main street. Lesson 2: pick sites that are popular now, you know – ones that other people are on.

Finally, I took my friends advice and signed up on a popular app. One where I got to write very little about myself but post half a dozen photos. Bingo! I was suddenly the most popular girl at the dance. So popular, I couldn’t possibly keep up with the amount of interest flooding in on a daily basis. It was exciting and fun, but I hadn’t planned on getting a part-time job that took hours of my day. Lesson 3: when you’re new to a popular site, you get inundated for a while with responses, something to do with being a newbie.

It’s difficult to sort the good guys from the psychopaths, so I used it as a fun game of ‘who should I date?’ with my girlfriends in our WhatsApp group. Reminiscent of Cilla’s Blind Date show except with a photo and bio. “Contestant number 1, a Buddhist yoga teacher with twin teenage daughters. Contestant number 2, city bloke with Savile Row suits and a Celine Dion fixation. Contestant number 3, Scottish kilt-wearing man with cheeky grin (enough said, got to love a man in a kilt). It was hours of fun, for us all. So many men, so little time. That was just it, I didn’t like the way the app turned it all into a pick n mix sweetie shop experience. We’re real people damn it! Almost doesn’t feel like real people somehow with the way they make us all approach dating; swipe, millisecond snap judgements, next – next – next syndrome. You find out there’s some dating professionals out there and they love a newbie, too smooth, too polished with it all. My friends explained this reptile just baths in the attention, seeking more and more female adoration for their hungry egos. Then there’s the ‘be gentle with me, I’ve been hurt’, women distrusters. Thankfully, a lot of these twats write their feelings on the hurtful callousness of womenkind in their profiles so they’re easy to avoid. Eyeroll emoji, we’ve all had our hearts broken, you’re not unique and it isn’t all women’s fault and it’s not our job to fix you, piss off! Oh, and the ‘I’m just a big kid at heart’, meaning; you’re an overgrown man-child looking for mummy – yeah, no thanks. Some will chat and flirt for a bit, others just the once, some are illiterate, others overly familiar and some think being overtly sexual and offering you dick-pics is sexy, it’s not. Others seem genuinely interested then just fade away when you ask to video-chat…. Worst of all, the married ones who just want to see if they’ve still got it and think wasting single people’s time isn’t doing anything wrong – you’re cheating you arsehole and it’s all kinds of wrong to both your spouse and the single person you’re conning. Lesson 3: People become jaded and fickle thanks to dating apps, instead of investing time in getting to know someone, they don’t really get to know anyone because there’s always someone new…

Be honest about what you want. In the few words I was allowed in my profile I made it clear manners are important to me and that I’m old-school. My first actual date was for lunch with a photojournalist who’d taken some award-winning war pictures and had recently taken up learning the piano. He was a couple of years older than me, and I liked the fact he was like me, still loved learning and creating. He’d lived in New York for some time and was now back in Blighty. I was so excited to be on my first date I ran up and hugged him warmly upon seeing him waiting nervously outside the restaurant. I told him he was my first date in 15 or more years and first ever via app technology. He said, “oh dear, and you got me,” with a smile. I liked him immediately. We went on four dates all together, ate some lovely meals in lovely places – which he picked up the tab for like a gentleman. I made a picnic for one of our dates and we took my dogs for a walk, I could see he wasn’t quite as much of a dog person as he’d made out. I enjoyed his company; he was intelligent and had some incredible stories. Also, being a journo, he had some interesting inside political gossip. Ultimately though he sensed that’s all I enjoyed, I didn’t fancy him, I didn’t want to kiss him, let alone sleep with him and he started dropping hints about ‘dating rules’ in New York and how everyone knew people slept together on the third date. I blithely told him, “How ridiculous! People should do whatever they want, not play by silly rules.” He wanted more than I could give him, so we amicably moved on. Lesson 4: People probably aren’t just looking for friendship on a dating app

I had some other dates, with a London artist who was good fun but overly keen. He wanted us to get engaged on date 3, way too intense. Then I met a guy that looked quite a bit older than his photos. He sat there over dinner and showed off about how much money he was making and then at the end of the meal asked me to pay – it was an inexpensive Asian restaurant. So tacky, I get that’s normal for a lot of people and I understand it but personally for me, if a guy can’t do the gentlemanly thing of offering to pay (even if you do contribute, at your own suggestion) then it just turns me off. One thing they all had in common, they were very keen to have relationships quickly. Lesson 5: when dating at over 50 the tables have turned, remember all those guys who didn’t want to commit in your 20’s? Well at 50 they can’t wait to settle down and you’ll be the one going, nah – I’m liking single life ta.

Then my wise young neighbour and friend, Sarah, came round for a cuppa and to have a word with me as we’d had a few previous cuppa’s and she realised what was going on…. I didn’t …. but I was about to be told …

“You are a young person; you might be 50 but you’re young and you look young and you’re youthful and vibrant and these men you’re dating look like your Grandad next to you”. “But they’re only a couple of years older than me,” I protested. “No, they’re not, they’re much older than you when it comes to compatibility.” “Oh,” I said. “What’s more, stop telling me you’re feeling anxious because you don’t know what to do about this artist who’s constantly hounding you to be his girlfriend, the one you’re avoiding but texting back, just to be polite.” “I do feel anxious about it, I don’t know what to do.” “Yes, you do, you know exactly what you want and it’s not him, just tell him, anxiety over – do it now.” So, I did, I told him the truth and Sarah was right, I immediately felt much better and very relieved. Sarah then asked for my dating profile, she changed my age range to include younger people and handed it back. “I see you with a tall, mixed race handsome man a few years younger than you”, she said.

A few days later I yelled to Sarah over the fence while she was gardening, “Here, come and look at this.” I showed her photos of the man I’d arranged to meet for a date that weekend. A handsome, 44-year-old, half Caribbean Brit, over 6 foot tall with a voice like rich coffee and custard creams. He’d popped up to ‘like me’ very shortly after Sarah’s intervention. A lion of a man, not backwards in coming forwards, he got onto voice and video calling soon after connecting. On those calls we laughed a lot and talked about everything under the sun, including reading the same books. I was really looking forward to our first in-person date. Lesson 5: always listen to your friends who love you, they know you best and only want what’s best for you.

Oh, and if you want to know how things are with the lion – read From Hell to Happiness – what a difference a year makes.

Published by JoJo

Confessional writer, starting over at 50 - I promise you brutal honestly with a few laughs along the way.

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