Ms. Adventure

Ms. Adventure: Cupid Knows Best—Doesn’t She?

Playing matchmaker for a fetching—very choosy—woman in her 50s sure stirs ripples in the dating pool.

BY June 6, 2018


I‘m a happily married woman who recently spent three weeks in the online dating world impersonating my single girlfriend in an effort to help her find her soulmate. And, boy, was it an adventure. As a modern-day, female, cyber Cyrano De Bergerac, I learned a lot about online dating after the age of 50 in Southwest Florida—and, trust me, it’s not for the faint of heart. It all started when my dear friend Wendy (all names are changed to protect the innocent and/or guilty) decided to effectively throw in the towel when it came to finding romance. An empty-nester in her early 50s, she’s been single for several years since the end of a nearly 30-year marriage. She’s smart, beautiful, sexy, funny and outgoing.

But, relationships are hard around these parts—especially for the ladies. I don’t have any hard statistics, but even if you just look around, the women outnumber the men by a lot. We have plenty of newlyweds, there are a growing number of young professionals, and we boast a huge number of retired folks. But, who’s out there for a 53-year-old career woman looking for a full-time resident with a decent job who loves to travel, dance and go to the beach?

That was Wendy’s challenge. Alas, there seems to be no such thing as a 9 to 5 job anymore, so she works nearly 50 hours a week. She loves to have fun on the weekends, but there’s also laundry, bill-paying and errand-
running—all of which leaves very little time for getting out there and meeting men. So, like many, she turned to online dating.

Whether it was Bumble, Plenty of Fish, Zoosk or Our Time (geared toward the over-50 set), she wasn’t having any luck.

Meanwhile, I happily consider myself a bit of a cupid-around-town—and I actually have a few successful unions under my belt that have turned into marriage and/or long-term relationships. Years ago, when I first started matching up friends, it was the old-fashioned way—in person. But, my last few couplings have happened when I helped girlfriends set up their online dating profiles, chosen their photos and helped them shop for dates. So far, there have been three marriages—originally online matches—that I helped facilitate.

Wendy was at the end of her rope. Her latest had been a guy in his 40s without a job who lived in his aunt’s guest house, and before that, a fellow who asked her to marry him on the first date. Things were getting dire. She handed over her online dating profile to me—and it turned out to be a big responsibility.

At first, I thought it would be fun. The three marriages that I took credit for in the past involved ladies in their 40s. But I soon found out that women over 50 had a whole different set of challenges. To put it simply: Most dudes in their 50s/60s seem to want to date women in their 40s; men in their 70s will gladly date women in their 50s. The problem was, Wendy didn’t want to date a man 20 years her senior. It became a numbers game, and the cards were stacked against us.

It worked like this: I set up her profile, wrote the narrative (with her approval) and even took her photos. I screened the men who “flirted,” “winked” or sent messages, and based upon her tastes, I reached out to men I thought would be good matches.

Our first stumbling block was looks. It turns out that Wendy and I have very differing tastes on what’s attractive and what’s not. I like hair, she leans toward sexy and bald; I like guys in jeans, she prefers them in crisp shirts or suits; I don’t mind tattoos, she’s not a fan. And it was important for her to see a photo before communicating with a potential date—“There has to be a spark,” she told me. A lot of the gents looked good on paper, but oftentimes their photos did them in. By the way, if you’re a guy looking to date online, I have some advice: Don’t post photos with your arm around your ex (even if you crop out the ex, we can still see her manicured fingernails on your shoulder). Please refrain from shirtless photos, no matter how hot you find yourself to be. And, please, get a friend to take a nice picture of you. Some of the bad selfies I ran across were deal-breakers.

It took some time, but I finally found a guy Wendy was willing to meet for a drink. He loved boating, he was nice-looking, and although he was retired and a bit older than she is, she kept her mind open. They met for drinks, and it wasn’t a total disaster that he lived in a mobile home and was on disability, but when he made some racial slurs and refused to tip the waitress, Wendy was out of there.

My next choice for her was not quite as “crisp” as she would have liked, but he sounded like fun. He was Canadian, loved music and lived on his sailboat. She agreed to meet for a glass of wine, but when he suggested that she see the sleeping quarters on his boat even before the glass of wine, he fell out of contention.

Undaunted, I continued my quest for the semi-perfect man, but I was showing signs of exhaustion. Online dating is like a part-time job (with no pay). As I mentioned, Wendy is cute, so her dance card was getting full. I was getting messages from boys in their 20s (“I know you might think I’m young, but I know how to handle a cougar—roar!”); age-
appropriate men, but some still married (“My wife doesn’t mind if you don’t.”); and much older men (“You look like a very nice gal, and I’m looking for a wife to keep me company. Do you golf?”). At first, I tried to answer everyone back politely, but after a week, I just started deleting with abandon.

Wendy went out with a couple of other men I set her up with, but none were matches. When my three-week Cyrano stint was over, I was more than happy to delete the online dating app from my phone and hand her the reins to her dating life.

I’d almost forgotten about the whole experience when, a week or so later, Wendy sent me a text with a guy’s online profile photo. “Who is this?” she asked.

I had to think about it, but eventually I remembered. I had sent him a “wink,” but he never responded. Wendy reached out to him again—in her own voice—and not only did he respond, but as of this writing they’ve been on a slew of dates. She thinks he’s wonderful and apparently he feels the same.

These days, I’ve been giving my husband extra hugs and winks and thanking my lucky stars that I’m not out there in the cyber dating world, but if Wendy and her current guy get married, I better get to be the matron of honor. Even an online cupid needs recognition for her efforts.

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