Sex & Relationships

Why Dating In Your 30s And 40s Can Be Pure Hell

As a professional matchmaker, I’ve helped dozens of women meet their one true love. But for every happy ending, I have many more stories of delusional expectations and rejection. Here’s what I’ve learned about the real nature of romance.
Why Dating In Your 30s And 40s Can Be Pure Hell

Photo, Rob Kittredge

I met Lana on a tour bus in Paris and we became instant pals. In your twenties, it doesn’t take much more than matching Canadian flag patches on weathered backpacks to cement your status as travel besties.

Lana was cute, whip-smart and sarcastic as hell. The more I talked to her, the more she reminded me of someone I knew. I went through a mental Rolodex of my female friends but just couldn’t place her. Later, she said something a bit geeky and I felt a jolt of recognition. The person she reminded me of was Cameron, a university pal.

I asked Lana if she was single (she was). I asked her if she had a type (she didn’t). I asked her if she’d be open to meeting a funny doctor with a penchant for bar trivia when she got back home (she very much was).

Five years later, I was toasting Cam and Lana at their wedding.

I started introducing single people to one another and they just kept falling in love (or, at least, lust). After the third or fourth like-minded couple dated courtesy of my meddling, I took a huge gamble. I walked away from the 9-to-5 job I hated and started my own matchmaking company.

Now, I had no actual training as a matchmaker. Yet somehow, lonely stranger after lonely stranger entrusted me with their money and their heart. Forty clients registered in my very first week. I was in business.

Gushing, grateful emails and smiling couple selfies started piling up in my inbox. For the first few years of matchmaking, I burst into tears at every client engagement, wedding invitation and birth announcement. It was good and meaningful work—with the added allure of having power over people’s fates. Early on, I remember seeing a production of Hedda Gabler. In it, the tragic anti-heroine says, “I want for once in my life to have power to mould a human destiny” and I sat up very straight in my chair.

The vast majority of my female applicants were in their 30s and 40s with amazing lives. A lot of them were homeowners and were absolutely killing it in their professional and creative endeavours. They were doctors, lawyers, ad executives, entrepreneurs, writers, politicians and powerhouses. But no amount of hard work could help them find love. These women were done with endless hours of swiping on Tinder. Done with the flakes on OKCupid, the crickets on eHarmony. Done with the disappointing set-ups by well-meaning family and friends. They were ready to find love, settle down and maybe start a family.


There was unfortunately one roadblock to running the ideal matchmaking business: there weren’t enough men in their 30s and 40s signing up. Those who did were mostly looking to date women in their 20s.

If you’ve ever been unwillingly single for more than a few months, I don’t have to tell you the romantic playing field is uneven. In general, people of all ages, shapes, sizes and appearances value the young, slim, tall and objectively beautiful. Straight men are particularly guilty of ageism in dating. I’ve had men in their 50s and 60s tell me their dating age cut-off for women is 33.

"Humans aren’t hot meals made to order. People aren’t paper dolls. I’m a matchmaker, not a magician."

That said, the women could be just as fickle as the men. One early client was a beautiful, stylish and successful woman in her 40s. She told me she wanted to date a tall (minimum six feet), handsome, never-married man between the ages of 40 and 50, ideally with salt and pepper hair. Oh, and also? He had to be a firefighter. I tried to talk her out of her rigid preferences, but she was resolute. I went home discouraged. How was I ever going to find a firefighter to ignite her heart?

The following week, a wonderful man signed up for the service. Who happened to be a firefighter. I practically leapt with joy and relief. But when I presented him to her as a potential match, she turned down meeting him…because he was 39—one year below her preferred age range.


That wasn’t the first or last time I failed to convince a client to be more flexible. I’ve tried, time and time again, to talk rigid clients out of unhelpful preferences. Thick hair doesn’t last and neither do washboard abs. Fancy cars chip and rust. Designer suits fall out of style. “Be open to what different people have to offer,” I’d tell them. “You might be surprised.”

Here’s the thing: You can customize just about anything you want these days, but you can’t customize a partner to suit your exact specifications. Humans aren’t hot meals made to order. People aren’t paper dolls. I’m a matchmaker, not a magician.

Eventually, my matchmaking successes were eclipsed by my frustrations. Clients would Google their dates before meeting them and reject the match, saying they didn’t find them attractive. Other clients would ghost on their dates or on me. Clients would write sad or angry emails when they hadn’t had a date in a while, or if it took too long to send them their first match. Sometimes they’d tell me I was pushing them to settle, when I gently encouraged them to go on a second date with someone kind but short. Or smart but bald. Every good match felt overshadowed by tantrums from people who came into the experience with difficult standards and questionable expectations. I started to wonder why I’d become a matchmaker in the first place.

There’s a lot to be said for helping people find love. So many people feel disconnected and lonely. But I’m done with the ugliness: later this year, I’m getting out of this business and focusing on other things. I’ve started a new career in communications. I’m working on a book of short stories.

And I’m spending lots of time with my partner. Last year, at the practically geriatric (for women) dating age of 37, I fell hard for a sweet, smart and funny man over Twitter. I may not have ended up with him had I not taken the advice I’d given to so many of my clients over the years.


He’s a little older than my ridiculously arbitrary age cut-off of 45 and is a quiet, thoughtful introvert—far from the gregarious comedian/actor/journalist/whatever I’d always imagined myself with. But our online chemistry translated big-time in person—we now have that beautiful cheeseball kind of love where I hear a Phil Collins song on the radio and think, “Holy wow! I totally understand those lyrics now!”

Had I come across my love on OKCupid instead of slowly getting to know him through his tweets, would I have given him a chance, despite our (totally unimportant and completely unnoticeable) 10-year age gap? I’m not sure. I’m so glad things unfolded the way they did.

Singledom can feel interminable, but if you’re openminded and know your needs, I have faith you’ll find your person, too. Despite having helped so many others find love, I was certain I was going to be alone forever. Now, I’m the luckiest person to have ever loved and to have been loved in return. But I had a professional matchmaker’s inside advantage: I got to learn from hundreds of other people’s mistakes.


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