This is (Dating Over) 40

Women’s tragicomic tales of dating in a world of swiping right.


Lila, a real estate agent, has internet-dated on and off for about seven years. She’s been on Lavalife, Match, Elite Singles, Ok Cupid and eHarmony, and has found more luck online than off.

She’s busy and finds the system efficient because she can peruse a potential beau anytime that suits her instead of trawling bars. “Dating online is fun as long as you’re light-hearted about it. You might not find your mate, but a good friend or a business associate.”

Her biggest frustration as a straight, single, over-40 woman, though, has to do with age. Finding a guy your own age is tough for a gal in midlife. The problem, says 50-year-old Lila, is that “most of the hits I get are guys under 34, like 65% of them.” She has no interest in a dude with a cougar fantasy. (All of the women we spoke to for this article asked to have their names changed for the sake of privacy.)

And yet a single girl’s gotta date, and doing it online can seem like a good place to start. Once the path that only a friend of a friend took, finding Mr. Right by clicking through profiles on a screen is now the norm. And it’s easy and efficient. Who doesn’t love being able to actively pursue love while wearing sweatpants?

Statistics Canada reports that a quarter of Canadians have tried online dating. According to Maclean’s magazine, there are 1,500 dating sites to choose from, many with millions of users. It may be tempting for some women to dream about joining the two million mostly successful marriages eHarmony says it has helped generate (the site also boasts a divorce rate of just 3.86%). Or with lighter expectations, they may surf over to Plenty Of Fish which offers fewer questions – and no fees – where the pond is stocked with 100 million users worldwide, with four million active every month.

For heterosexual women who find themselves single after a long absence from the dating scene, it’s true what you’ve heard: Not all of the candidates on the other side are of superior potential. And a shallow dating pool can be an especially tough place for a more mature swimmer.


“Maybe he hates boobs.”


“I could have been getting a bikini wax, or massaging my dog’s feet,” says Carmen, a pretty 45-year-old with a dirty blond mane and pouty lips, ruminating on a recent date gone wrong. Instead, she was in Owen Sound, Ont., lured there for the day by a semi-attractive man (“geeky in his earnestness to please, but cute,” she says), whom she had met on Match. He had promised she would enjoy unwinding in his woodsy hometown, but he had never revealed just how gung-ho he was about religion. (When he had asked her about her own religious beliefs, Carmen had just said “non-practising Catholic.”)

Now here he was confessing the depths of his faith. “He asked me if I was friends with Jesus and if I thought I was getting into heaven,” says Carmen. He also declared himself a prophet, revealed he was homophobic and insisted women should be submissive to men as per the bible – all after a month of lightly dating.

After the prophet, Carmen booked a date with a dentist she met on Match. “He drove a Porsche and had a condo and in his mind, he was beyond good looking. He said to me,’ Do you know how many phone numbers I have? Over 9,000,'” she says. “He was the biggest whack job – he was nuts.”

Mid-way through their meal together on a Yorkville patio, he told the server to take away Carmen’s plate, even though she was only half finished eating: “The difference between a hippie and a bohemian is that a bohemian never finishes her meal,” he said (whatever that meant).

Carmen sat stunned, unleashed a torrent of epithets in her native Spanish and then left.

Is this how it will all go down as you grow older, you with your stories and a circus of cats to keep you warm at night?

Sydney, a whip-smart 55-year-old writer who has been dating online for 14 years hoping to find the one to finally settle down with, had a similar experience years ago when she met up with a man for the first time at a bar on the Danforth area of Toronto. For two minutes he stared at her cleavage, then told her he was going to feed the meter – and never returned.

“Where did he park, Oshawa?” she thought. “I think he’s done a runner.” Sydney is certain he wasn’t into her physically. “Maybe he hates boobs?”

When you’re in your 20s, outrageous dating tales are expected – a hilarious rite of passage. But by your 40s, those multiplying mating mishaps begin to feel more like tragi-comedy – a little beneath one’s dignity at this age, frankly.

It’s enough to lead you to wonder: Is this how it will all go down as you grow older, you with your stories and a circus of cats to keep you warm at night? And is it better to be set up through friends or are you more open to a large, anonymous playing field? Lavalife and other mainstream sites may have their oddballs, but just consider who you could unearth at (it’s love in the buff, folks!), (because bread haters who hate together stick together), (what’s that saying about the size of a guy’s golf club?) or (where you can fulfill your fantasy of being Missis Krusty).

Literal clowns aside, if you are over 40, you might want to bypass the dating app, Tinder, where 53% of the audience is between 18 and 24, and rumour has it that it’s more for hookups than happily-ever-afters. You would have better luck on the paid site, eHarmony, if you can get past the 400-plus questions on sign up. (Just be aware that eHarmony rejects would-be daters who say they’re separated on the questionnaire – only the legally unattached need apply.)


What does work when it comes to attracting the fellas? Carmen acknowledges it’s women who look good in their photos who get dates. Horrible as is sounds, Carmen’s view may not be anecdotal – over at Plenty Of Fish, the people behind the site say, women who describe themselves as “thin” receive 41% more messages than the average user.

“Internet-dating is human shopping, it’s a catalogue,” Carmen says, likening the experience to buying a Fendi clutch. “Men don’t read what you write. You can talk rubbish but if your pictures are good, it’s fine. If you’re larger, forget it.”

Women go into the game with shallow concerns as well. While guys are into waist circumference, women are into wallet girth – a Plenty of Fish survey found men who make between $100,000 to $150,000 receive 42% more messages. (Other sites that advise users to reveal their financial status include Match, OkCupid, Tinder and eHarmony.)


Despite the daunting barriers, Cathy went into online dating with an open mind, motivated mostly by the fact that she couldn’t meet someone her own age. It was the number one irritant for the youthful 50-year-old, who rides her bike to work, listens to indie music (and has played in bands on and off for decades), and generally wasn’t ready to swap her G-string for granny underwear just yet.

“I set up a profile on eHarmony and put down my age, which at the time was 46,” says Cathy, who is now in a relationship with a man she met offline. “The only men I met were well into their 50s and 60s because men in their 40s want to meet women in their 30s.”

Cathy’s tip to bypass eHarmony’s filter: lie. “Then explain yourself in the profile.”

Some men lie about their age, too. Lila, the 50-year-old real estate agent, has learned to be wary of elders in disguise: Men who front as 40-something in their profile but appear way older in person.

“Misrepresentation really irks me,” Lila says. “On one first date at a cafe, I hid behind a shrub to see what he looked like – he was nothing like his photo,” she says. “This sounds terrible, but I just bailed.”

Fibbing about your age and coming clean right then and there is one thing, but at least one expert says you should never post photos that misrepresent what you really look like – a prime complaint of both sexes.

“The only men I met were well into their 50s and 60s because men in their 40s want to meet women in their 30s.”

Amy Webb, the author and math wizard of the memoir Data, a Love Story, writes about finding love via an exhaustive list of algorithms.

Webb also counsels singles to forgo aerial view shots that distort one’s body, and heavily filtered photos that make it look like you’ve never smiled a day in your life.

As for written content on your profile, she says keep it light, upbeat and specific. (When Webb herself was new to online dating, she posted her actual C.V. – not exactly the sexiest teaser.) Webb is now happily married with a child to a man she met online, but back when she was dating, she required men to fulfil roughly 72 bits – not an exaggeration – of her own criteria before she would date them.

While researching the book, she also posed as a man so she could read the most successful women’s profiles. Webb found them to be “easygoing, youthful and spontaneous.” Also, they were short. No wordy dissertations, but instead snappy, succinct profiles did best (she knew these women did best because their profiles were consistently at the top of the search – at least that’s what Webb insists; it’s not entirely clear if this is how the search algorithms work).

Meanwhile, somewhat depressingly, overachievers in real life turn out to be underachievers when it comes to attracting men. Webb found that many men were turned off by women who bragged about climbing Mt. Everest or getting into Harvard at 15. “These are the types of details to work into a conversation,” Webb says.

But not so fast. Don’t schedule that date at Chez Philippe’s before make sure the man is worthy. In a Guardian interview, Webb says, “It’s not always easy to see if someone’s stretching the truth when you meet them online. I recommend talking to someone on the phone a few times, emailing back and forth, before meeting them in person.”

Sydney, the writer who once scared a man off with her chest, agrees that being a high achiever can strike men as even scarier. “I think it freaks dudes out that I have my own house, my own dreams.”

Should it really be shocking or off-putting to men that middle-aged women can talk about lives filled with accomplishments?


Still, Sydney’s main frustration is the same old problem: age. In her never-ending quest to try to crack the online dating code, it has come down to this: “They want younger, no matter how saggy and old they are.”

It’s not as if all the middle-aged fellows out there are ticking all the boxes themselves. Says Sydney: “Seriously, I can’t look at one more selfie of a dishevelled lonely guy bathed in sickly blue computer light.”

And maybe that’s the rub: Both sexes need to lower their expectations and be open to giving an unlikely candidate a chance. Maybe they will be surprised at what they find – Carmen was.

She’s now engaged to the 49-year-old man of her dreams. She met him on Tinder, of all places.

This is (Dating Over) 40
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