It was 2018, and I was recently divorced. My life, and the dating world, had changed drastically from when I first met my ex-husband in the supermarket in 1985. Now everyone was looking for love online, and I had no idea where to start.
I had been around the block of love and loss, and I had just retired after more than 30 years in marketing. I was living alone in my Boston apartment and taking full advantage of everything going on in the city. I went to the theater and museums and attended lectures. I was independent and thriving in so many ways, and yet, faced with the prospect of coffee with a stranger, I felt like a schoolgirl all over again. I hadn’t dated in so long I wondered if I’d be attractive to anyone.
I understood that finding dates now mostly happened online and that I needed to learn the art of swiping. I was terrified and curious. What if no one wanted to go out with me? Who would be out there looking for a 62-year-old woman?
I learned about Bumble, a popular dating app that gave women an advantage with the first swipe: If I wasn’t interested in the man, he couldn’t contact me. This seemed ideal, so I picked up my phone and downloaded the app.
I was immediately asked to create a profile. I had no idea what to say about myself, so I asked my friend Deb to write it.
I love everything that Boston has to offer. You might find me sailing on the Charles (just learning), playing golf (always learning), or enjoying walks along the harbor. Could we share some discoveries or laughs? Hope so.
Deb threw in golf, even though I could take it or leave it.
“Men like golf,” she advised.
Man with no shirt on a boat holding up large fish. No thanks! Swipe left
Man with no shirt on the beach, arm around babe in bikini. Left
Man with no shirt on deck at a barbecue. Left
Then I found the first man with potential. I nicknamed him “Zadie,” which means “grandpa” in Yiddish. My friends were so excited to see me go out for the first time that they overlooked his photos, which to me screamed “sweet old man” more than “hottie.”
“But look at that picture where he’s holding up his hand to show off his Fitbit,” one of my friends pointed out.
“The first date is like making the first pancake of a batch,” Deb explained. “It takes a few before you get a good one.”
Zadie and I agreed to meet for dinner. I tried a million outfits while getting ready, and after finally choosing dark skinny jeans and ankle boots with a tank top and pleather jacket and putting on a little eye makeup, I was ready for my modern dating debut.
I saw Zadie through the revolving glass doors as I entered the restaurant. He turned and smiled when he saw me.
“You’re even more beautiful in person than online,” he told me.
I was stunned. I hadn’t heard anything like that in a very long time.
As it turned out, Zadie wanted someone to cook and clean for him in exchange for trips to see Broadway shows. I had no interest in that arrangement, but his opening line motivated me to keep looking.
I made lots of pancakes. Dinner at a sports bar with an engineer who was disappointed I didn’t drink a lot. A walk with a retired technical expert in satellite radio who told me he was sapiosexual, which meant he was only attracted to women he found intellectually stimulating. I respected his identity, but I wasn’t sure what that meant for me — was I supposed to discuss quadratic equations over dinner?
Dating had become a process of tossing out pancakes and hoping a good one would finally materialize in the pan. I was trying to be open-minded, but I knew I didn’t want to take care of someone else’s laundry or cook their meals. I didn’t want to have to get drunk to enjoy someone’s company. I didn’t want to have to prove my intelligence. So I kept swiping.
Courtesy of Andi Pollinger
In October 2018, I met Carlo, a 65-year-old software engineer from Milan who was now living in Toronto. We talked for hours on each of our dates. One night, I invited him up to my place after dinner. I opened the door, and, before I could toss my keys onto the table, he pulled me close and gave me a deep kiss. My knees went weak. I hadn’t felt desire like that in so long.
We shared a wonderfully romantic relationship for about 15 months until the pandemic hit. With borders closed, we couldn’t see each other anymore. It was time to move on. Still, our relationship convinced me that even at 65, I could love and feel desire again. I wanted romance, so it was worth the effort to find a partner who wanted it, too. Back to swiping.
By December 2020, the height of the pandemic, loneliness had set in. I woke up day after day to a quiet 750 square feet of space, a silent phone and a mostly empty email inbox.
The dating world shifted to Zoom. I made a date with a tennis player whose better days were behind him (and I could see a ton of crap behind him when he appeared on my screen for our video date). This wasn’t going well.
Then a well-meaning friend suggested I try Tinder Gold.
Ugh, I thought. Tinder? Really? Isn’t that just for hookups?
I’m no cougar, and I definitely wasn’t interested in quick sex. But my loneliness was undeniable, the pandemic lockdown didn’t seem to be ending anytime soon and I figured this could be another way to meet a partner. What did I have to lose?
I made my first match, a civil engineer I called Mr. Rotterdam. He shared a moving story about losing his best friend to COVID, and after chatting on the app for a couple of days, I gave him my phone number.
It wasn’t long after he began to text me that I realized I had stumbled into the “wild west,” where catfishers and scammers abound.
“You are so sweet,” he wrote. “I think I’m falling in love with you.”
We hadn’t even met! I immediately stopped texting, blocked his number, hid my profile and reported the incident to Tinder.
As I continued dating, I became more confident about what I wanted in a partner. Surgeries for breast cancer and a broken pelvis from a car accident had left me with numerous scars, and I was anxious about how a date might react to them. However, my relationship with Carlo convinced me that the right man would look right past all that and see those scars as symbols of the stories that helped shape who I am today.
Warm spring weather, vaccines and the ability to meet in person again renewed my energy for dating. I had coffee dates that went nowhere. I had conversations with guys who were either afraid or unwilling to drive into Boston to meet me (parking can be a nightmare).
One guy told me, “Wow, you look just like your picture!”
“Who else would I look like?” I asked him.
“You’d be surprised,” he replied, and then he spent the rest of the date telling me all the reasons he didn’t like any of the women he’d met.
“This is demoralizing,” I told Deb.
“There are a lot of pancakes out there,” she offered. “Don’t give up. You’re a great catch, and the right guy is waiting to find you, too.”
Online dating was hard. I needed my friends to support me.
By September 2021, my enthusiasm was starting to wane. With just four weeks left on the Match.com subscription I had purchased, I decided to give dating everything I had before I gave up.
I sent a message to a guy named Rick, whose profile intrigued me. He wrote that he was interested in a relationship but equally open to friendship. He said he was, more than anything, looking for stimulating conversation about technology, art or perhaps virtual reality if someone was particularly knowledgeable on the topic.
I knew I was a decent conversationist, but I know very little about software. Still, I figured, what the heck? I liked his photos, too — they showed off his tanned skin and deep-set eyes, taken in locations including Brooklyn and at different art museums.
“Sure, I’m up for a walk and some heady conversation,” I wrote to him.
Rick and I met for an iced coffee and made an unexpected trip into the federal courthouse across the street from the cafe to see the red, blue and yellow paintings by Ellsworth Kelly on display there.
What guy knows these paintings exist in such an obscure location? I wondered. I wanted to learn more about him.
We went to the Museum of Fine Arts on our second date.
What single guy has a membership to the MFA?
We toured his favorite exhibits. Rick showed me a scholar’s rock standing in the corner of one room. In an atrium, he pointed out a melted and shattered porcelain block that shone when the light hit it just right. Through the art, he was introducing himself to me.
Courtesy of Andi Pollinger
We talked for hours about contemporary design and unique textures, history, politics and philosophy. We went on more dates, had more conversations and, eventually, I had a weak-kneed moment like I’d had with Carlo.
I realized that dating at my age meant I wasn’t facing any of the pressures of being on the hunt to settle down and start a family, so I was free to be myself and seek what would make me truly happy. Every time I met a new man, I concentrated on how I was feeling, not on the impression I was making. On every date I asked myself, Am I attracted to this guy? Am I listening to him? Do I feel listened to? Is he curious about me and my life? If I answered no to any of those questions, I moved on.
I also realized dating could also be an adventure. Every time I learned about a new dating app, responded to a “like” emoji or met a stranger for a date, I took a flying yet courageous leap. As the dates accumulated, I was less afraid and more excited to put on makeup and get out there. I met an astrophysicist, a geologist, a journalist and so many other different kinds of men that I’d never encountered when I was a working mom. Dating got me out of the house a few times a month, and I usually had an interesting conversation with whomever I met, even if he didn’t turn out to be my perfect match.
It’s been two years since my first deep kiss with Rick, who is now my partner. We have no intention of getting married or even living together. We talk about the future — about aging. We plan to be there for each other when things like stairs or driving become challenging. We’ve even signed up for CPR classes to take care of each other in case of an emergency. Since we likely don’t have 30 years to grow together, it drives us to make the most out of this second chance at love.
If you’re wondering what really happened in the fantasy suite on “The Golden Bachelor,” let me just tell you that at this age we can take our time to explore and savor. Because of that, the sex is better than ever.
We’ve traveled to South Korea, Venice and Tokyo. When issues arise between us, we work through them using negotiating skills we’ve acquired through age and experience.
On the front of the holiday card Rick sent me in December was a photo of a special place we had visited in New York. On the back, he wrote, “Lots of memories, but just a small portion of what I hope lies ahead for us.” I’m living my best life. I hope every woman over 60 looking for love gets a kiss that makes her weak in the knees.
Andi Pollinger is 67, retired and living in Boston. The topics of her Medium essays run the gamut from surviving breast cancer to living in a van with her 25-year-old son while taking a road trip across America. Her essay “Honk for Choice” is featured on Herstory, and “A New Grandmother Finds a Seat at the Changing Table” can be found on Parent.com.
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