What It’s Really Like To Online Date In Midlife—And How To Make It Better

Set a hypothesis, experience new things and then evaluate your results with a generous heap of self-compassion.
A woman with grey hair stands against a blue backdrop, holding a phone in her left hand and a mug in her right hand(Photo: iStock)

“Frustrated, disappointed, petrified!”
“Lots of creeps.”

I’m on a Zoom call with a dozen open-hearted but nervous midlife women who have gathered for a two-hour workshop on how to get back on the dating scene after a long absence. We’re all here because we crave connection, companionship and possibly some romance with a side of hot sex. But when asked what thoughts “online dating” conjure, most of us seem to have experienced the kind of traditional heteronormative relationship dynamics that makes one wince before downloading a dating app.

The “How to Meet a Man Online” workshop is being run by Anne Bokma, journalist and author of My Year of Living Spiritually: From Woo-Woo to Wonderful—One Woman’s Secular Quest for a More Soulful Life, and her partner Amit Karia. Both are in their late 50s and met online after their decades-long marriages ended. They each met about 20 people before finding one another (and starting their company, Chapter Two Dating.)


“So many women we know are frustrated and fed up with online dating. Yet they are lonely,” says Bokma. “We wanted to share what we’ve learned and give people a sense of hope that if they persevere, know what they are looking for and employ a few strategies, it’s entirely possible to meet someone great online.”

Coincidentally, I was co-hosting my own dating event two days after Bokma and Karia’s. As a life coach, I help women connect with their desires and stop settling. But as a single-again 40-something who believes in using apps as a way to meet a wide range of people, I was curious to see how a dating webinar run by a man and woman who met on an app might be different.

Here’s what I’ve learned about online dating at midlife.


Adopt a helpful mindset before downloading a dating app

If you’re trepidatiously dipping a toe back into the dating waters, take a deep breath—and then starting thinking about online dating as a fun experiment: Set a hypothesis, put it into action, collect data on what you like and don’t like and then evaluate your results with a generous heap of self-compassion.

My hypothesis in April 2020 was: “I wonder if I can meet someone funny, intelligent and socio-politically aligned with my values, who is willing to get to know me at a distance during pandemic lockdowns?” (The answer? Yes!)


Other hypotheses might be:

  • What if I could meet someone who loves the same hobby or activity as me?
  • What if there’s someone out there who wants what I want, too?
  • Other people seem to meet people online. Is it possible that I might meet someone great online, too?

My own online dating experiences have ranged from “I could write a stand-up comedy set about this,” to “I could write a love story for the ages.” I won’t sugarcoat it—dating can be daunting, especially now that technology offers the fastest way to find other midlife singles. Apps can take a while to figure out, but before you download one, it’s helpful to assess your current state of mind.


Start by noticing any unhelpful thoughts. Repeating “all the good ones are taken” isn’t prime for swiping.

Remind yourself that just because you haven’t found the right person or people yet doesn’t mean they aren’t out there. Look for role models: Is there a coworker, relative or friend whose relationship helps you remember that there are good partners out there?

Get clear on the “what” and “why” of dating


So many women I talk to approach finding a companion similar to how they approach a to-do list, which is guaranteed to lead to frustration. Take some time to reflect on your motivations for meeting new people. Why do you want to date? How much time can you reasonably give to another person? Are you looking for something serious or casual?

Midlife women often enjoy an empty nest and a higher disposable income for experiences, and companionship for trips and meals out tends to be a motivating factor in dating again. But what about sex? Does it matter to you? How much is enough? And do you want to see multiple people or date one person? If you’re an active person, do you want someone who gets moving with you or someone who encourages you to relax? A homebody may be looking for another couch-lover, or someone who will shake them out of their comfort zone. Some apps, like OKCupid, can help by guiding you through clarifying questions on a variety of topics, from your stance on social and political topics, to specifying your favourite books or movies. (I unapologetically swipe left on anyone who says Taxi Driver.)


Once you’re clear on what you want and why, it’s time to get started on your search.

What are the best dating apps for women over 40?

The best dating app is the one you find most comfortable. While Bokma and Karia met on Tinder, I met my last partner on Hinge and I’ve also had success with OKCupid. Remember, what works for someone else might not work for you. Karia’s advice: “If it’s free, give it a try!”


Once you find a platform you like, Bokma recommends paying for bonus features, like being able to see who likes you (so you can see if you might like them back) versus liking or swiping on random profiles without the ability to determine a guaranteed match.

How to write a dating profile

“I took a point-form approach,” says Karia, whereas Bokma adopted a lengthier description. Bokma says she could tell Karia was very funny right off the bat, thanks to a playful comment about being “more like [comedian] Russell Peters” in reference Karia’s South Asian heritage. Bokma advises. “Try to be original and avoid clichés. If someone was reading your bio and they didn’t see your picture, what would they know about you?”


She suggests writing two paragraphs: one about who you are and one about what you’re looking for. Include one or two “deal-killers” at most. Focus on communicating what you do like more than what you don’t.

How should you choose a photo for your online dating profile?

Living in an ageist, ableist and fatphobic society, you might be apprehensive about what photos to share. But if you want honesty in your relationship, you need to post current photos.


What makes for a great photo? A nice, natural smile and a display of personality, intelligence and a sense of fun. “Smile!” Bokma encourages. “A big beautiful smile puts people at ease and says you are a positive person—and isn’t that what we all want? Positivity!”

Karia was drawn to a photo of Bokma confidently but casually posing with her bike. Bokma was charmed by Karia’s photos, which showed him smiling next to a dog in one photo, and invitingly holding a bottle of wine in another in a way that made you feel like he was about to pour you a glass. “He just looked like someone you’d want to meet,” she says, “Warm, open, and friendly.”

Use photos that are no more than one or two years old. Include a full body shot and make sure you seem approachable—only cross your arms if you can also tilt your head and smile in an open way.


Keep your photo background clutter-free and make sure there are no exes or children in your photos, both for their privacy but also because it sends an odd message.

Other considerations when online dating in midlife

Step outside of your comfort zone


“Consider widening out from your usual parameters,” says Karia. “Maybe the guy is a little shorter than what you normally go for. Maybe he’s a few years younger than you. I encourage people to widen out from what they typically gravitate to. This exposure could push one through any cultural stereotypes or biases that they might not even know that they have.

“Be open to possibility. Remember that life is full of surprises.”

Have a thick skin


Don’t take rejection personally, says Bokma.

Set a time limit

Consider how much time you want to spend on the apps, and don’t let online dating take over your life.

Adjust your expectations


“Some women… want a guy who is six feet tall, handsome and handy, makes great money and knows how to wine and dine them. These things are pretty superficial when you think about it,” says Bokma. “What really matters is character, values and personality. Yes, you have to be attracted [to], but be wary of the smooth-talking players and look for the guys with substance.”

Be selective

“For every time I swiped right, I probably swiped left about 100 times,” says Bokma. A healthy amount of skepticism will also help you stay safe. Catfishing—when someone is not who they pretend to be—is on the rise, so if you see a Brad Pitt-type, it’s possible they aren’t who they say they are. Do a bit of research before you give them personal information or arrange to meet up. Ask them some key questions. For instance, if they say they are from a particular city or town, or have a certain profession, ask questions that only someone with that experience would know to validate that they are who they say they are. And don’t be afraid to Google them or look them up on social media.


Make the first move

Get to the first date as soon as possible to see if there’s a true possibility for connection. Then approach that first date with a sense of calm, confidence and positive energy. Choose a low-pressure activity in a public place, like going for coffee or a walk in a popular spot. “Say to yourself, ‘I’m just meeting somebody,’” recommends Bokma.

Have a strategy for wrapping up the first date


When you’re ready to say goodbye, let yourself off the hook with a casual “Let’s think about how things went.” Be courteous, but remember that you don’t owe anybody anything. Use the app’s security features and block anyone with unacceptable behaviour. “Don’t give people too many second chances online,” says Bokma.

“We’re proof positive that online dating works,” says Bokma. “We want to give others a sense of hope that it can work for them too.”

Armed with tips on how to make dating apps work even better for me this time around—plus the experience to back it up—this hopeful romantic is looking forward to meeting the next person with whom it just… clicks.


Editor’s note: This story has been updated to add context to a quote about dating outside of your comfort zone.

Originally published February 2023; updated March 2024.


Subscribe to our newsletters for our very best stories, recipes, style and shopping tips, horoscopes and special offers.

By signing up, you agree to our terms of use and privacy policy. You may unsubscribe at any time.

This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply.