Over-50s dating sites: The men I met on Match.com, Dating Over 50 and Tinder
January 8, 2016 | By:
When Rosanna Dickinson, 52, goes on three online dates, the men don't match their photos, lie about their age, and worry more about property prices than personal hygiene
Online dating at 50_the dates

Rosanna was looking for fun, banter and flirting. Did she find it?

Last week I reported on my exploration of online dating for over-50s and discovered which are the best sites for us (and which aren’t). Despite my initial trepidation about putting myself so out there I was soon ‘winking’ at and connecting with (and dismissing) so many men I could barely keep track of what I’d told to whom.

Finally I narrowed it down to three men I’d like to meet IRL (‘In Real Life’ – I know all the lingo now). Here’s what happened, and the ten things I learnt about online dating over 50.

Date one: ‘Unicorn’ (found on Match.com)

I nervously head off to a coffee shop in Marylebone for my date with Unicorn, the horned (and possibly horny!) stallion. His name is Steve, a father of three, grandfather of four. He is six feet tall, wearing a tweed jacket, and much more decrepit than his online photo. He is presentable and polite, but has appalling bad breath and is old enough to be my father.

He says he’s pleasantly surprised to meet me (what was he expecting?) and the monologue, as it turned out to be, begins. He is retired (obviously), comfortably off, and has travelled for his work in construction. He shows me pictures of the flat he has bought, tells me how much he bought it for, how much it’s now worth and about the planning permission for his new extension. Yawn.

He asks where he should put the kitchen. I don’t think our relationship has got far enough of me to have an opinion on this.

The only other question he asks me is whether my children live with me. He doesn’t ask any questions about them; his only concern is if they are going to get in the way of this burgeoning (not) affair.

He says he has been online dating for many years but never felt a connection with anyone. I restrain myself from suggesting that asking questions and being interested in the person in front of you may not go amiss. As I make my excuses to leave he puts his head on one side and, with labrador eyes and an air of desperation, asks if he can see me again. No way, granddad.

Date two: Peter (found on DatingOver50)

This one has possibilities: with a little imagination his profile picture could be of him on a private jet. We meet in the bar at St Pancras station. He is nice looking but shabbier than his photo, wearing a checked shirt, jacket and jeans.

Through email we are up to date on children, music and travel. He is easygoing, asks what sports I’m into and what kind of holidays I like, and the conversation flows.

He’s been on Dating Over 50 for three months and been on 15 dates. He says each of the women lied about their age and their photos were clearly out of date. Honesty, he felt, was crucial in this game, at which point I gulped and came clean – I had given a fake name.

His approach to online dating was to go into it with an open mind and just enjoy the encounters. Treat it like a game, he said. He certainly felt he had his money’s worth.

Peter was fun, and nice, and normal (whatever that is), but he too had that labrador look when I said I had to leave. He texted within ten minutes saying how much he had enjoyed meeting me, what great company I was and that he would be in touch.

Of course I was flattered but to play a good game, I thought, there must be an element of cool, even if meeting through a dating site. He was good company but I couldn’t see it going any further.

So when he texted again the next day, I let him down gently (I hope) with a carefully worded text. I do honestly hope he meets someone as ‘nice’ as he is. (Maybe ‘nice’ is not what I’m looking for…)

Dating over 50_Rosanna and Tinder date

Rosanna and ‘Rajiv’ meet in Soho


Date three: Rajiv (found on Tinder)

Two days later I meet Rajiv in a Soho coffee house. He is in his early forties and we instantly agree this not going to lead to a relationship of any sort, and that’s fine. So, thankfully, he doesn’t ask any boring questions.

Instead, he teaches me how to tweet and we have an interesting chat about his political convictions. He tweets a lot about his disappointment in Obama. I liked his tweet on the latest Marina Rinaldi advert, which claims that ‘women are back’; he rightly tweets ‘where have they been?’.

I ask if he’s had any sexual encounters through Tinder but he admits only to late-night sexting, which he finds a big turn-on. He politely says he will leave it up to me to be in touch. I hope he realises his dream of buying a tea plantation but we won’t be going on a further date, much to his relief, I think. And there definitely won’t be any late-night sexting.

Is online dating worth the effort?

Even though none of my dates was successful, yes, I think it’s worth it. It wasn’t as scary as I first thought, and it builds your self-confidence.

I enjoyed the email exchanges with potential dates but was frustrated not to be asked out more. I was doing the running and turning into a predatory female, which i didn’t like.

Each date was polite and blind dates are initially exciting. But it takes only a few seconds of meeting for disappointment to set in.

I was trying this because I’ve been single for two years, since my husband died. But he is a hard act to follow and I don’t think his successor is busy uploading photos of himself on to these sites. But it can be successful for many.

Start with a three-month membership, and use a good profile photo, where you look happy (I was more drawn to the photos than the written profiles). However, I found that what you write has a big effect. When I said I was looking for fun, banter and flirting I got a lot more interest than a straightforward description of myself.

It is time consuming: you really have to filter through the men on match.com, and I might have had more success on Guardian Soulmates if I had lightened my tone. More photos and an upbeat tagline certainly helped on Dating Over 50. Tinder is purely visual but irresistible, and I still can’t help wondering who’s waiting round the corner now…

Ten things I learned about online dating at 50

• Nobody looks like their photo. They are all shabbier and greyer.

• Everybody lies about their age.

• You know within two seconds of meeting if there is a spark.

• Men of a certain age all ask the same questions.

• Men of a certain age all talk about property prices.

• I may be feminist in every other way but I still wanted the men to ask me out.

• Not everybody is after sex. None of my dates mentioned it (except Rajiv, because I asked him).

• Conversation and companionship are of greater importance to most.

• Your profile and tagline are of utmost importance. Find your USP. Give a sense of mystery and excitement.

• It can be fun and shouldn’t be taken too seriously.


Read the truth about online dating for the over-50s


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