The Ultimate Guide to Online Dating in Your 40s and Beyond

We asked the experts how to make it less stressful and more fun, so you actually get excited about logging on and looking for love.
Guide to Online Dating

One night last October, I was lying under a blanket, googling the best dating apps, vaguely wishing someone would jump out from my laptop and tell me everything was going to be OK. There I was, 40 years old, fresh out of a several-year-long relationship and overwhelmed. I wondered: Was the partner I yearned for an algorithm-away in one of these Silicon Valley digital inventions? If so, how would I ever manage to find him in this online dating sea?

My head throbbed. I closed my windows, texted a few friends, and went to sleep. 

Months later, I got an email from my editor here at Scarlet Society asking if I’d like to write a story about online dating and, as she wrote, “how to make it not suck.” In essence, I was being charged with finding out how to get in on the game in a way that feels good. 

Yes, I thought. I want to know how to do that. 

The “old-fashioned” initiation of a date—which, for my generation, has often meant something like spilling coffee on a fellow Metro rider only to then get their number a few minutes after—seems to be long gone. Dating apps have taken over. But I never got the memo on how to properly use them. Or make that, on how to feel like me while using them. 

The truth is, I’m not alone. Research shows that online dating, with all its benefits, can induce a sense of dread. A study published in 2020 links depression and anxiety to the use of online dating apps. Another recent study finds being a user of swipe-based dating apps is “significantly associated with having psychological distress.” And The Pew Research Center data shows that half of Americans who have used a dating app or site leave the experience feeling frustrated.

I know online dating can be a great thing. It’s just that it can also be tough. This is especially true as we venture into mid-life. In our 40s, 50s, and beyond, dating requires a physical, emotional, and mental gravitas that isn’t as heavy in our earlier decades. There are children. Divorces. Financial wins and losses. Health concerns. I’m quick to call this baggage. But Andrea McGinty, founder of 33000Dates, is even quicker to correct me. “You have life experience,” says McGinty, who coaches people in their 40s, 50s, and 60s on how to make the most of online dating.

As we talk, McGinty casts a megawatt light on the truth: Finding connection online when you’re over 40 doesn’t have to evoke anxiety or fear. With a mindset shift and a few clear touchpoints to follow, it can be enjoyable—and, as McGinty tells me, a total win: In 2020, more than a third of people got married or into a long-term relationship with someone they met online, she says. “Online dating can be a great way to meet people later in life.”

So, instead of going down another blanket-covered rabbit hole, I asked McGinty and other experts for their take on how to make online dating not suck. Turns out, swiping can be more than a harbinger of what’s to come. It can be a cool study of the self. 

Tip No. 1: Get Clear on Your Values

Who you spend your time with is a reflection of you, which is why making room for people who share a similar outlook on life leads to richer relationships. Yet this can get lost in the dating world, says dating coach Allison Wellington. When we’re not clear on who we are and what we’re looking for in a partner, it’s more likely we’ll find ourselves “disappointed three or six months down the line, when this person isn’t who we thought they were,” she says. 

To avoid this, Wellington adds it’s important to get clear about what you want—and what you’re looking for—from the start. The best way to do that? Write down your “non-negotiables.” What’s essential for you in work, life, family, ethics, culture? What life lessons have you learned from your first several decades of life that you want to weave into a new relationship? What’s important to have in a partner? “Then, use that list when you’re looking at a dating profile trying to assess whether or not that person may be a good match for you,” says Wellington.

Related: This is the Couples Counseling Advice That Didn’t Work in My Marriage—But That I Live By Now

Tip No. 2: Get Witty with Your Words

The messaging in your profile is the special sauce. “This is a huge part of how you market yourself,” says McGinty, who says she too often sees people flailing in this department. “I have a client who is a best-selling author in her 50s. I read and love her books, but you should see what she writes about herself!” 

The key is to get flirty, fun, and creative with what you put on your dating profile, adds McGinty. Let’s say you’re an avid traveler. Instead of listing the 40 countries you’ve traveled to, which McGinty says can scare someone off, you could spin it to: Adventurous? I hiked to the top of Machu Picchu, even though I nearly fainted several times as I looked over the cliffs. “This is cute, it’s fun, and it’s not boring” says McGinty. 

Use the same wittiness for your direct messages. The great thing about being at the mid-life point or beyond is that we know what we want and what we don’t want—so own it, says McGinty. Get specific by homing in on a few salient points from someone’s photos or messages and write to those in a way that really sounds like you. McGinty shares an example of one man’s profile that read, I never leave home without my passport and Siracha. The response she coached her client on: My passport is dusty, but I’m ready to put it back to use…

Tip No. 3: Post Fun, Recent, Honest Photos

That shot of you hiking Camelback in 2009? It’s great—but it doesn’t warrant a spot in your profile, says life and dating coach Alison Marie.

Here’s the deal: Choose recent photos that show you feeling good and “like your best self,” says Marie. Also, mix up the contexts to offer a glimpse into your life. “You can have the ocean nearby, maybe a cute restaurant you go to, anywhere it’s interesting in the background and also represents the things you enjoy doing,” says Marie. But go easy on the filters, and limit photos with friends or family to only a handful. (You want people to know it’s you when they look at the photos in your profile.) Wondering if you should post photos of your children? McGinty says it isn’t necessary, almost every dating app will have question about kids that you can answer there.

Related: Should You Date a Younger Man? 

Tip No. 4: Choose Your Apps Wisely—and Don’t Overwhelm Yourself

There are roughly 7,500 online dating platforms worldwide, according to the dating service review site DatingWerx. A giant mistake Wellington sees her clients make is inundating their phones with too many dating apps, which leaves them totally overwhelmed. 

Instead, choose two apps that are popular in your city and vet them thoroughly to see if they offer a fit in terms of the demographics and values you’re seeking. “If you want to date Christians or Muslims, or if you want to date Black or Asian because you want someone who understands your culture, research the apps ahead of time,” says Wellington. 

Related: Interested in an alternative dating site? Read all about one woman’s experience on Feeld here.

Also, turn off your alerts. Be intentional about checking your profile rather than letting random alerts drain your attention, says Wellington. “You don’t need for your phone to beep or vibrate every single time someone sends you a message.”

Tip No. 5: Stay Positive

Find yourself spiraling into complaints and negativity when you talk about online dating—or seeing a whole lot of negative talk on the profiles you’re seeing? It happens to the best of us. Wellington sees it everywhere in the online dating sphere: “I’ll see men say, ‘If you’re a gold digger, don’t reach out to me.’ I’ll see women say, ‘If you’re an F-boy, don’t swipe on me,’” she says. The aim is to find someone who aligns with you, “but there’s a way to word that so you’re not coming off negatively.” 

Instead, reframe your language to put the emphasis on what you do want rather than what you don’t want. Statements such as “I’m looking for a committed relationship” is the classy, positive equivalent of “Don’t waste my time,” says Wellington. 

Just as important is staying positive about the way you talk about your adventures in online dating. “Saying ‘this sucks’ and ‘I hate this’ over and over is only going to make your experience worse,” adds Wellington. By putting out the good vibes, and you’ll be more likely to attract good people in return.

Tip No. 6: Keep a Sense of Wonder

It’s normal to let our past inform our present. But when it comes to dating, doing that can sometimes stifle us, says Marie. This gets particularly true as we hit our 40s, 50s, 60s, and beyond.  

“If there have been bad relationships in the past or a marriage that ended, there can be hurt feelings that come up that you could potentially project onto new dates,” says Marie. It’s on you to reframe this. After all, every prospective date is a new opportunity with an entirely new person; try to engage in online dating with curiosity, openness, and wonder. 

“It’s managing and working through our life experiences—where we’ve been, where we are now, and where we want to go—to see how we can approach it in the way that’s going to best serve us,” adds Marie. “That’s going to best help track what we really want in our lives.”

Stacey Lindsay is a multimedia journalist, editorial director, and writer based in San Francisco. In her 16-year career as a writer, reporter, and producer, Stacey’s storytelling has been featured on national and international platforms. She was the articles editor at goop and served as an evening news anchor and reporter in The Four States region. She also worked in the film industry as an associate producer for James Caan’s production company, JEC Productions, and as marketing coordinator for Magnolia Pictures. To learn more, visit staceyannlindsay.com

Join the discussion! Did you meet your partner on a dating app? Are you online dating now and loving (or hating!) it? We’d love to hear about your experiences navigating the online dating world here.

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