When I was newly divorced at 50, I knew it wouldn’t be a cinch to meet single men my age. But I thought I had a leg up. I am outgoing, I live in a big city, and I have a life’s worth of friends. I expected at least some of those friends might set me up, but that never happened. (Have you noticed that married couples tend to socialize with other married couples?) I expected I’d meet people at my local coffee spot or at the gym, but that never happened either. I went to alumni events, joined a boat club, and checked out various meetups, but single, heterosexual men between 40 and 60 seemed in short supply. After six months, I realized that if I wanted to date again, I would have to go online.

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My first dip into digital dating was tentative. I was mainly focused on protecting my dignity and my wallet. I asked an old friend to take some pictures. That evening, I created a free account on OKCupid, uploaded a few photos, and wrote a short, breezy profile that, in hindsight, probably sounded a little flip. 

Here’s the first line of this first profile: “I want to say I love my bike because it allows me to get exercise and fresh air, but really it’s because it’s the only way I get anywhere on time.”

I was, at least superficially, up for the adventure. When I received a message sent by an impish looking younger man with the handle “Eyeballtron,” I thought, “Why not?” A few days later, I met Eyeballtron at his favorite bar where the house drink was called Ass Juice, and hardcore music blasted from a 1980’s jukebox. I couldn’t determine if he was attractive or not, because he barely looked up from his Subway sandwich except to rage about his parents’ divorce, which had left poor Eyeballtron deeply troubled. 

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Behind the Bunny and Other Lessons

Resolving to stick with men nearer my age, I next met a guy whose photo won me over at first glance. Directly beneath his sandy hair and squinty blue eyes was a baby bunny he was holding up to the camera. “Adorable!” I thought, and messaged back saying I’d be delighted to meet up in a nearby park. As I approached the bench where my date was sitting, I was shaken to discover what the bunny had been hiding: several wobbly chins and a sagging beer gut. I pulled myself together, sat down, and what started as a conversation about his documentary film work turned quickly into a bitter monologue on his financial woes. Onward, I told myself.

I was shaken to discover what the bunny had been hiding.

My early dating experiences were sometimes hilariously awkward, sometimes sad, and often disappointing. But they had their lessons. Figuring things could only get better, I started on a mission to learn the ropes and to share whatever I learned with other divorced women. 

I went online as a man looking for “women” to see what other women were posting. I talked to “experts”—usually professional Cyrano de Bergeracs—who wrote dating profiles on behalf of shy or busy clients and coached them through the first dates. I interviewed men who met their second partners online. 

Getting Real

My research led me to change a few things up. I rewrote my profile so it was more in sync with where my heart was (a little less brassy, a little more vulnerable). I shared about some of my quirkier hobbies, including swing dancing, which one friend dubbed the “ultimate male mate repellant.” I even replied to the prompt for an embarrassing story and answered questions about sex. Honestly. All of this made my online message exchanges more engaging if not more frequent. Then I made the biggest leap and did something that would horrify my dear, late mother: I hired a professional photographer to take my photo.

Then I made the biggest leap and did something that would horrify my dear, late mother.

I won’t lie, the process was excruciating, particularly because I ended up doing it twice. The first time I was too sheepish to disclose the real purpose of the photos, pretending they were for work, and sure enough, they looked perfect for a convention brochure. Ultimately, I shelled out a good bit of money. That was painful too. But OMG, what a difference it made!

The day after I posted my new cover photo, I noticed there were suddenly much more appealing faces greeting me in my inbox. And there were lots of engaging, entertaining, and substantive messages that I actually wanted to respond to! About a week later I received a notification from the dating site. “You’re popular! Because you have some of the highest message traffic on our site, you will now start to see more attractive matches.” Leaving aside the general ickiness of our image-obsessed culture and this company’s questionable algorithm, it helped change my attitude about the whole endeavor. I morphed from the quaking new kid in school to someone who could find her way around, and (gasp!) even have fun on campus.

Hitting the Jackpot

Pettus today with her sweetheart

I dated online for almost six years, taking breaks to give a promising relationship a try or to focus on kids or work, or just because I needed a refresh. One of the rituals that never failed to refresh me was a twice monthly lunch with my friend, Jenny, also divorced and also exploring the zany world of online dating in midlife. We swapped stories about the characters we encountered, the meetups, the breakups, and of course, the sex!

We were constantly reminded that middle-aged men have at least as many hangups as we do.

We were constantly reminded that middle-aged men have at least as many hangups as we do, which, if sometimes frustrating, was also reassuring. We’d become less inhibited, more confident, and more curious. We often wondered aloud at our wild, uncanny luck: at an age when many of our friends said they were done with sex, we were having the best sex of our lives! 

Eventually, we each met someone who stood apart from the blur of faces we’d been swiping on. The man I met turned out to be someone whose life was oddly parallel to mine, but who was six years older and lived two hours north. When he first reached out, I joked to a friend that this guy had to be a bot.

“Why?” she asked me.

My reply: “He says he actually likes to swing dance.”   

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