I Wasn’t Ready For My Parent’s Dating Drama

We all want our folks to be happy. But how do we feel about them jumping back into the dating pool? Love and life with my newly single father-in-law.

older parents dating

Navigating our older parents re-entering the dating world / Illustration by Adriana Bellet

I knew what was going on months before anyone else did.

My father-in-law had been acting shifty, shooting up to New York for days at a time with no explanation, talking broadly about shows he’d seen and new restaurants he’d tried, vaguely tossing around the word “friend,” dancing cagily around details. He’d started dressing more sharply, too, swapping baggy khakis for slimmer-cut jeans and wearing stylish Warby Parker sunglasses. I’d brought up my suspicions to my husband gently, laying a framework for what was sure to come: “I think your dad has a girlfriend.” He’d shrugged it off, but I wasn’t surprised in the least when his dad finally confided to me during one of our weekly coffee dates that he was seeing someone.

I was thrilled. It had been a little more than a year since his beloved wife of 40 years, my mother-in-law, died, and my husband and I worried constantly about his loneliness, his health, how he was dealing with this world that kept on spinning even though, for him, it had stopped.

At that moment, he was dealing just fine. His new girlfriend (well, not exactly new; they’d been seeing each other for several months by then) had whirled into his life, a brash divorcée from Queens who worked in his industry and promptly decided that along with my father-in-law’s saggy pants and dorky sunglasses, Mom’s Hummels and wallpaper had to go. (To be fair, she was probably right about all of it.)

We liked her enough, and when Dad needed an emergency triple bypass, she stayed with him for weeks while he recovered, taking a lot of the pressure off of us, busy with a toddler at home. But she had a full life in New York, and he had a full life here in Bucks County — or “Candy Land,” as she referred to it, always with a tinge of disdain. Neither wanted to remarry or move, so there was never a prospect of them being more than longish-distance companions, which was fine with all of us.

Sometime later, my father-in-law and I were back at the coffee shop. He needed relationship advice. He’d been on and off with Queens for a while and had finally broken things off. There was a new woman in his life now, this one from Connecticut, a friend of his cousin’s. Queens didn’t take the breakup well, and I understand why. At 75, my father-in-law is kind and funny, tall and newly stylish, with a nice shock of white hair that makes him look quite distinguished. He’s a catch, which is why two women are in love with him, why he’s been texting me constantly — to vent, to worry, to gush, to ask for advice, to ask for more advice — and why I’ve suddenly become an unlikely relationship therapist.

“I mean, look at me!” he says, shaking his head as if he, too, can’t believe we’re here. “Who would have thought that at 75 years old, I’d be needing dating advice?”

“I know,” I tell him. “It’s insane.”

But it’s not, really. Plenty of people his age are getting back in the dating game after decades of marriage — more now than ever. Part of it’s basic numbers: People are living longer. In fact, the world is on the cusp of being the oldest it’s ever been; by 2030, one in six people will be 60 or older. And while divorce rates for people in their 20s and 30s have declined, splits between couples ages 50 or older doubled between 1990 and 2010. There are catchy terms for this shift: “gray divorce,” “silver splitters.” A 2019 study found that 36 percent of all divorces were of couples in their golden years.

All of this to say: Our parents are getting back out there, and like it or not, we kids have a front-row seat.

A few months later, I find myself sitting alongside Alberta, a spry 98-year-old, 90 pounds soaking wet, a tangle of snow-white curls corkscrewing from her head. We’re at my parents’ house for an early dinner, and she’s spilling all the details about her first kiss with her new boyfriend. “It’s like he plugged me into an electrical outlet!” she says. She grasps my hands and leans forward, staring at me intently with watery ice-blue eyes. “Things lit up inside me that I didn’t think worked anymore.”

My mom squeezes her eyes closed, and my husband laughs gleefully, egging Alberta on, as he does every time she recounts this kiss, which is quite often. It would be cute, a story about finding passionate romance in your 90s — and sure, it is rather cute. But Alberta is talking about my 100-year-old grandfather, so it’s also a little bit weird.

“Who would have thought that a man my age could fall in love again?” Pop-Pop says. We were all a little bit surprised, to be honest. My grandfather was devoted to his wife of 72 years, and when she died in 2020, we thought he’d soon follow — death by heartbreak. But instead, he got a girlfriend named Helen and wheeled her and her oxygen tank around their senior living facility. But Helen wouldn’t even hold his hand — doing so would be unfaithful to her late husband — and her wheelchair became increasingly difficult for him to push, especially with that tangle of oxygen-tank tubes. Then Helen got moved to the memory-care building up the hill, and my grandfather had trouble making the walk, especially now that he needs to prop himself up with a cane. So after mulling it over with my mom — who, like me, suddenly found herself playing relationship therapist to her dad — he broke up with her.

Cue the feeding frenzy.

“The women all went crazy trying to get him, so I knew I had to be first,” Alberta tells us, again. Like my father-in-law, my grandfather is a catch: same kindness and sense of humor, same tall build and impressive shock of white hair. He doesn’t look a day over 80. So Alberta took things into her own hands. She grabbed him after the senior home’s annual Christmas party and invited him up to her apartment to see her holiday decorations. They kissed by the glow of her Christmas tree. (Hey, when you’re in your 90s, niceties get a little crunched; there just isn’t time for all that wining and dining.)

I felt like my mom became a teenager again. She’d skipped all those crazy years of dating in your 20s, so it was like she reverted back to that.”

After they became an official item, some ladies wouldn’t sit with Alberta in the dining hall. “What are you going to do when he dumps you?” one quipped. I wonder if all these women have adult children coaching them through this disappointment. More fish in the sea, more men at bingo.

My friend Nikita had to coach her mom, now 61, through the dating process after her dad died in a motorcycle accident 11 years ago. After the flurry of chaos that surrounds a death had settled down, her mom was left alone, dealing with a world that had once again stopped spinning for someone.

“My mom was so lost,” Nikita explains. “She’d been with my dad for basically her entire life. They started dating when my mom was 15 and got married when she was 18. She was like, ‘I don’t even know how to clean my gutters.’” (Honestly, her mom had been too busy to worry about gutters: She’d had their first child at 16, another at 19, and then Nikita at 26.) “She had to learn how to be a single person again.”

It took about four years for her mom to find her sea legs, and once she did, she plunged into the dating pool headfirst.

“I felt like my mom became a teenager again. She’d skipped all those crazy years of dating in your 20s, so it was like she reverted back to that,” says Nikita. Her mom became a serial dater, one who went to bars and had one-night stands and got ghosted by jerks. And Nikita heard about all of it.

“There were times when I felt like I was the parent having conversations with her and giving advice. At one point, we had to have a very serious talk where I told her that there’s a fine line between ‘I want you to be happy’ and ‘I want to know things.’”

“What’s fascinating is that there’s a real role reversal going on,” says Michal ­Naisteter, a Philly-based matchmaker. “Our parents are the ones who have always guided and supported us, but now we see them in a vulnerable situation. Now we’re the ones who have to support and advise them. Your parents are supposed to be caregivers. When you see them shift out of that role, it can be unsettling.”

But of course, our parents already know what this feels like. They’ve gone through it with us — helping us navigate the dating world, coaching us through breakups and first dates, squeezing their eyes closed when we talked about kissing, driving us home from movie theaters and parties and ­dances. Yelling at us to be home at a reasonable time, to keep the lights on when we’re hanging out in the basement, to …

“KEEP THAT DOOR OPEN!” my friend yells to his 14-year-old-daughter, who’s currently upstairs in her room with her boyfriend. His wife shakes her head.

“You’ve got to calm down,” she tells him.

It’s a few weeks after the dinner with my grandfather and Alberta, and my husband and I are at our friends’ house for dinner, the four of us drinking wine around their giant kitchen island. For a while, their daughter had been downstairs, too, regaling us with stories of the ninth-grade dating scene. It all sounded exhausting, but she seemed energized by it — the buzz of drama, the fizz of excitement, the pinning of hopes and planning of futures with a kid who can’t even drive yet. We’d waited nervously for the boyfriend to arrive, and when he finally did, we all played it cool. He shook our hands, made good eye contact and pleasant small talk, and when they eventually retreated upstairs, the four of us looked at each other in silent appraisal: He’s nice, right?

We discuss the boyfriend they’re dealing with for a little while — the one upstairs — and then the conversation shifts to the girlfriend we’re dealing with, the one in Connecticut attached to my father-in-law. We’ve finally met her, and she’s fantastic, a (soon-to-be-retired) high-powered financial adviser in her 70s, never married, no children, kind and generous and super-stylish. My father-in-law blushes around her. Blushes. They hold hands all the time.

It’s a funny thing to be here, caught in a dating middle ground, sandwiched between two generations wading into the dating pool — our kids, our parents.

“You’re seeing so much change happening above and below you,” says Michal. “It really makes you look at the individuality of your kids and your parents.”

My husband and I used to make out in cars and talk on the phone for hours. I remember when we nervously met each other’s parents for the first time. We had a fiery near-breakup once, too. But that was ages ago. Now it’s late, and our friends’ daughter’s boyfriend is getting picked up, and we have to wake up early for our son’s basketball game, and isn’t his uniform still in the washing machine? We’re in the thick of things now, where there’s little time for electrifying romance. Hell, some of our outlets are probably still baby-proofed.

Oh my God, I think. When did we become the boring ones?

Gerry Turner is floating over Southern California in a rainbow-striped hot-air balloon. The 72-year-old widower is on a date with Ellen, a 71-year-old pickleball fanatic and retired teacher from Delray Beach, Florida.

“Have you ever been kissed at 100 feet?” he asks her. She hasn’t, so Gerry kisses her, and I cheer from my living room couch. I’m on Episode 3 of The Golden Bachelor, a spin-off of the long-running Bachelor series that features Turner searching for love among a pool of women ages 60 to 75. The show premiered last fall and set a streaming record as ABC’s most-watched episode of an unscripted series ever on Hulu. Who knew that 70-somethings making out in hot-air balloons — and on roller coasters, in hot tubs, and while literally rappelling down a waterfall in Costa Rica — would be so watchable?

“There was a fire in that balloon, and that’s what I felt,” Ellen tells the camera after the kiss. “A spark isn’t even close.”

Two episodes later, a tearful, excessively earnest Gerry sends Ellen home. She looks stunned at first, and then her eyes glaze with tears. I imagine her two adult sons watching this, think how painful it must be to see your mom dumped in front of 4.4 million people. And then I imagine the three adult sons of Queens, my father-in-law’s ex, who probably felt those same twinges of pain.

“It’s a lot to carry someone’s heart,” Michal the matchmaker says. “Jealousy, resentment, rejection, romance, desire — these are huge feelings to watch your parents go through.”

Ellen dabs her eyes as a stretch limo ferries her away from the Malibu mansion where all the women live during filming. (A mansion, by the way, that isn’t exactly equipped to host 22 senior citizens. Four to six women are squeezed into each bedroom, and some have to scale bunkbeds. “I need the bottom,” a woman named Sandra said upon assessing the sleeping situation. “I’ve had my knees replaced.”)

“I was falling in love with him,” Ellen continues. But her heartbreak is tempered by something bigger. “This experience has been one of the best experiences of my life. I have a lot more optimism about love and the possibility of finding love at this stage in my life.”

Perhaps that’s why this show about seniors dating like teenagers has become such a cultural phenomenon: America loves a second chance, the comfort of knowing that the world does keep spinning, the hope that even if your course changes, what waits around the corner might be something good. Maybe even something electrifying.

I think of my grandfather, who recently asked me to change the photo on his phone’s lock screen — a smiling Norma, his wife of 72 years — to one of Alberta. (“Oh dear God,” my mom said. “Really, Dad?”)

I think of Nikita’s mom, learning who she is after being married to her high-school sweetheart for 33 years, and then I think of our friends’ daughter, dating her own high-school sweetheart. Who knows? Maybe they’ll make it. (Or maybe not. In the end, Gerry Turner’s search for love ended in divorce after only three months.)

I think of my son, who will one day date someone, who will one day get his heart broken, maybe break someone else’s. It will be stressful, I know. As Michal says, it’s a lot to carry someone’s heart.

I think of my father-in-law and his Connecticut girlfriend. She says she’s been waiting her whole life to find him. He says he hasn’t felt this way since his wife. We went on a double date with them recently. My husband drove us back home to Candy Land, and even though my father-in-law is tall, he wanted to sit in the back seat with his girlfriend. I looked back once, and my father-in-law’s legs were pretzeled against the back of my seat, and his girlfriend was looking up at him and giggling, and they were holding hands like two teenagers in love. And I reached over and held my husband’s hand, just like I did when we started dating all those years ago.

And guess what? There were sparks.


Published as “Second Chances” in the June 2024 issue of Philadelphia magazine.