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Be a Winner in the Digital Dating Game

Join the wave of singles finding lasting love on the new generation of dating sites for people over 50

By Robyn Griggs Lawrence

When online dating became the way to meet people a decade or so ago, I was safely married — but weirdly, I felt like I was missing out on something. It seemed like fun, if a bit overwhelming, to shop for dates the way I might hunt for boots at
Single friends and colleagues were meeting interesting people left and right and striking up passionate romances with people they’d met online. And when dates didn’t work out, they'd tell hilarious stories about the debacle. This was a world I would never get to experience.
Five years ago I got divorced, and the gates to that digital-dating domain — more massive and confusing than ever — finally opened up for me. In those intervening years, online dating became my generation’s preferred way of meeting potential mates, according to a survey commissioned by And other research shows that people over 50 are joining online dating sites at twice the rate of other age groups. 
At one popular site,, boomer traffic grew by 173 percent last year, and two of the stalwarts, and, also report that boomers are their fastest-growing demographic. And we’re not just dating. According to Time magazine, 1 in 4 boomer marriages are the result of online dating.
Online dating is big business. The $1.9 billion industry is the Internet’s third-largest revenue producer — making more money than porn. The dating services are well aware of the data: 30 percent of (the 80 million) boomers are single, and we comprise 20 percent of the online dating community. No surprise, then, that Internet advertising is fat with ads for 50+ dating sites.
Another factor fueling this online dating trend: Newly single midlifers don’t feel like there are many options for meeting other singles. We don’t generally hang out in bars, our friends don’t throw parties every weekend (and the ones we go to seem populated with couples). Our flirting skills are rusty to nonexistent, some of us are still too preoccupied with work or kids to go out, and when do we go out, unless it's specifically an event for "mature" folks, everyone is 27.

(MORE: Deeper Dating: A New Approach to Finding Love)
So Many Sites, So Little Time
I’m not saying I was ready — or willing — to try online dating, but as I was researching this, I discovered that there were at least 15 dating sites geared to boomers. So I figured I had a decent shot at honing my own rusty skills and possibly finding an age-appropriate boyfriend. But where to begin?
Million-member-strong, which is owned by the same parent company as, describes itself as “a dating site that not only understands what it is to be over 50, but also celebrates this exciting chapter of our lives.” I can interact with people there for $20 to $71 per month.
For $30 per month, another popular site,, offers over-55 dating for “friendship, pen pals, romance or marriage.” I’m a bit young for that demographic: The people in the ads look like my parents’ friends (though interestingly, all the guys have hair). is “for mature people, with young heart”; claims to be “the No. 1 dating service for local singles to meet other baby boomer singles”; at, “everyone is screened”; and promises “sincere baby boomers looking for long-term relationships today!” With an exclamation point!
The “Boomer Singles” section of is free, but most of the profiles featured on the home pages are 20- and 30-somethings with usernames like freebird and slackerdude. Friends tell me these are not uncommon monikers. I can’t decide which is worse: those, or the unapologetic emphasis on “senior” at places like and
If I do dip my toe in the digital dating pool, I don’t want to waste a lot of money. But it’s hard to assess the real costs. Almost all the sites offer a free trial, but once that expires, membership can get pricey. And companies can be cagey about fees. On a number of them, it’s almost impossible to get that information until after you’ve signed up for the free trial, then they start trying to upgrade you.

(MORE: 6 Steps to Create a More Photogenic Online 'Stamp')

Online Dating Just for Us
Most people know at least one couple who met online and are, at least ostensibly, living happily ever after. Jill, 48, a friend of a friend, has been with her boyfriend, Mike, 58, since they met on two and a half years ago. I figured if anyone could inspire me to try this, she could.
“There are two types of daters,” Jill said when I called her. “Those who think a mate will just come to them and people who consider finding one a part-time job.” I was pretty sure I knew which camp I fell into.
She goes on to explain that she had been proactive and methodical, wading through 2,000 profiles in a single weekend, then emailing the few dozen that seemed interesting and assessing what came back to her. “I’m anal as hell,” she said, “and someone who doesn’t bother to use spellcheck wouldn’t be able to stand me.”
Jill selected her “finalists” by phone, which resulted in 12 enjoyable dates over six months. Unfortunately, none of them were quite “it,” and she was about to end her membership when someone reached out to her. Mike told her that she was the first person he contacted because she met his two requirements: at least 5 feet 10 inches tall and living within five miles of his ZIP code. Fifteen minutes into their first date, he asked her out again.
“Is he the guy I thought I would end up with in a long-term relationship?” Jill said. “Probably not. But he pursued me, which was nice for a change. He is funny, successful, artistic, an overall nice guy, and we have fun together. I’m almost 50. I’m just trying not to make the same mistakes I made in the past.”
Jill and Mike’s story offers hope for Type AAs and slackerdudes alike. Looking for a little more motivation to give it a shot, I called the public relations people at, which partnered with AARP in December to run a dating service for that organization's members. They put me in touch with 51-year-old Los Angeles-based Dina Mande, who has been online dating for about a year and a half.
Mande hasn’t found her man yet, but she hasn’t lost her enthusiasm. She said she loved HowAboutWe’s unique format, which lets users post and respond to potential dates rather than cruise profiles. (“How about we get some tea and do the crossword like an old married couple?” is an actual suggestion from a 50-plus member, which makes me a little depressed. What would we do for our second date, play bingo?)
Mande, who has been on that site for two months, said she got only two responses to her posts suggesting such dates as a jazz concert at LACMA and lunch by the pool at the Loew’s on Ocean Avenue — both from younger men. I’m shocked. Her profile is witty and charming, with stunning photos. If I were a guy, I’d hang out at the pool with her.

(MORE: Why Middle Age Is the Best Time to Fall in Love)
My Life in Five Sentences
Thanks to Mande and Jill, I decided to bite the bullet and sign up for a free trial with, which necessitated my creating a Gmail account to absorb the shrapnel. The first thing I noticed was that the men in the home page promo look to be about 30. This is not a cougar site, though that’s not a bad marketing strategy. boasts more than 3.4 million members.
When it came time to complete my profile, I failed. I considered carefully crafting answers to the questions about my perfect Sunday or my life in five sentences to entice the kind of man I wanted. That led to an hourlong reverie about my dream guy, and I couldn't go on. I felt too … exposed … putting my photo and date ideas up there for people to respond to (or worse, not respond to). And when I checked out men’s profiles, I felt like the worst kind of cyber-voyeur: looking and judging while refusing to put myself out there.
I had asked Mande what she likes about online dating, and she said that it had led to some real connections with good men and that it was worth wading through the clichéd profiles if she found one who stuck. “And now I have the opportunity to go in with more experience, patience and enthusiasm,” she said. “I’m really looking forward to the next relationship.”
I am too. And while I’m 99 percent certain that I won’t find it online, I have clicked open a few of the “daily date” selections that get sent to my Gmail account. Because there’s one thing I've learned: When you’re waiting for your mate to just come to you, it pays to keep every door open.
Robyn Griggs Lawrence writes and speaks about healthy homes and wabi-sabi, the Japanese art of finding beauty in imperfection.

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