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Go Fish: How I Hooked My Mom on Online Romance And Ended Up as Her Dating Coach

January 26, 2015
by Rachel E. Gross

I was 22, my sensitive vegan boyfriend had just dumped me, and my life was over.

Now I circled the park in my running shoes, trying to smooth over the jaggedness of the past two hours. No such luck. Every footstep was a lonely echo, every smiling family I passed another cruel reminder. There was only one thing left to do: I slowed to a walk, and called my mom. “I’ll never date again,” I announced.

This was met with a sigh, and what I could only guess was an eye roll. “Stop being ridiculous,” my mother said. “After all, there’s plenty of fish.”

For her, my life with a path unfolding, littered with men as various and multicolored as piles of autumn leaves lining the sidewalk. How could I make her see: that he was my first, my writer of verse, wearer of V-neck tees, fellow purveyor of used poetry bookstores, my one singularity? That for me, there could be no other fish?

Oblivious to my anguish, my mother corrected herself.

“By the way, I don’t mean that metaphorically,” she said. “Plenty of Fish is the new dating site I’m on. You should try it!”

My mother’s foray into online dating had begun six months prior, in a hotel room. She was in San Francisco for a work conference and I, a college senior at UC Berkeley with nothing better to do on a Friday night, had crossed the Bay to visit her.

Growing up, we had never been close. I found her cold and aloof; she found me frivolous and excessively boy-crazy. But hotels had a way with my mother. It was something about the clean white sheets, sky blue walls, perpetual coolness on her skin and an everlasting supply of tiny toiletries that made her calmer, more approachable. And that night, between her new, softened demeanor and two glasses of Chardonnay, I was feeling gutsy.

“I have an idea,” I said, casting her a sidelong glance. “Let’s make you a dating profile.”

She shrugged and said, “Sure.” Could it be: my mother, divorcee and staunch second-wave feminist, was willing to let her 21-year-old daughter steer her romantic future? Instead of questioning this unlikely possibility, I flipped open my laptop and navigated us to the OKCupid homepage. “It’s easy!” said the smiling cartoon woman onscreen, one elegant arm outstretched, imploring my mother to enter her gender and sexual orientation. “Signing up takes 2 minutes and is totally free!”

Soon, we were inputting her favorite hobbies (travel, gardening), breed of dog (all), the first thing people noticed about her (“my squinty eyes?”), and six things she couldn’t live without (“you and your brother…isn’t that enough?”). We hit publish, and were granted access to OKCupid’s inner circle: the Daily Top 5, the endless scroll of men. “Oh, Rachel,” she said, laughing, “this is just like!”

All in all, it was one of our more tender bonding experiences, I thought afterwards as we drifted to sleep in the queen-sized bed. Who knew? Perhaps this was the start of something beautiful: a mature friendship between two consenting adults.

Two weeks later, she called me in a panic. “What the hell did you do?” she yelled. She had received, I gathered, an e-mail from an online suitor.

I stepped out of the campus library to muffle her shrill tones. “Don’t you remember?” I asked, hurt that she had so quickly forgotten our magical night together. “You’re supposed to talk to them—that’s the whole point.”

“I thought we were playing a game!” she cried.

Unsatisfied by my repeated assurances of “yes, it’s safe” and “no, they cannot figure out your home address, or hack into your bank account, or steal your medical records,” she sought counsel from more age-appropriate friends. She was in for a shock: not only did they confirm that online dating was a thing, but many of them were already on it.

“You haven’t been on a date in ages,” they pointed out gently. “Why not give it a try?”

What could she do? She relented.

The day of her first date, I was home on spring break, pacing the kitchen nervously. She was already an hour late.

What if he was awful? What if she was lying in a ditch? Worse, what if the experience scarred her so badly that she never tried dating again, and it was All My Fault? I felt like a parent driving with my 16-year-old for the first time, fighting the urge to slam down on some set of imaginary brakes.

My moth­er’s in­box con­tained mul­ti­tudes: the black ac­count­ant with the Jag­uar, the real es­tate agent with the iguana, the en­vir­on­ment­al law­yer with a taste in high art. “Why not?” she said. “It’s just a first date.”

The doorknob turned. “Rachooo?” The voice was hers, but the woman who entered barely resembled my mother: her lips were pink-glossed, her hair fell in bouncy curls, and her feet ended in a flash of candy-red toenail polish. She kicked off her sandals, marched into the kitchen, and slammed her purse onto the counter with a note of finality.

“Well?” I asked, hardly able to contain myself.

The date had been perfectly mediocre. Ron, as he was called, had taken her to a sports bar, where she found herself yelling over some awful competition that involved a lot of grunting. Then they’d walked along the beachfront, an activity that left him struggling to match her brisk stride. “And that’s not all,” she said, leaning close as if to confide a great secret. “Rachel, he was round.” This fact seemed to make her positively gleeful.

I thought I could see why. Ever since the divorce, my mother had studiously avoided the opposite sex. She preferred to invest in things that gave back: things like her career, or her prodigious shoe collection. After 15 years on her own, the prospect of romance loomed before her, alien and intimidating. With this date, she had finally proven that she could interact with a human male in a romantic setting.

Now, as she darted around the kitchen, magnetically ushering crumbs from their hiding places, there was a bounce in her step.

“Did you like anything about him?” I asked, feeling that at least one of us should be empathizing with Ron.

She thought for a while.

“His eyes,” she said finally. “They were blue.”

Soon I was back at Berkeley, writing long theses in anticipation of my graduation date, while my mother too was graduating: from OKCupid to the big leagues. Within weeks she was on to, Plenty of Fish, AARP’s senior dating website, and even, briefly, JDate. (“Too many beards and yarmulkes in my inbox,” she concluded.) Every time I called her, it seemed, she was out with a strange man.

What impressed me most was her open-mindedness. Unlike most women her age, she felt little pressure to settle down, and could therefore approach dating with a lightness, a genuine curiosity about all the types of men she’d missed out on. The feeling was mutual: A dazzling variety of men, it turns out, are interested in a professional, petite 55-year-old woman. My mother’s inbox contained multitudes: the black accountant with the Jaguar, the real estate agent with the iguana, the environmental lawyer with a taste in high art. She entertained them all. “Why not?” she said. “It’s just a first date.”

And so I found myself in a strange position: I had become my mother’s dating coach. Did I think this break-up e-mail “conveyed the right tone”? she wanted to know. Was this babydoll dress from the juniors department of Macy’s appropriate? Was she allowed to date two men at once, as long as she didn’t make either official? (Answers: yes, no, yes.) “Isn’t it strange,” she would say, turning around so I could judge the questionable length of her hemline, “to think I gave birth to a friend?”

Several strange men later, my mother met Brian. He was fun, she giggled to me afterwards, spontaneous, a real hoot. A former actor, Brian had suggested on their first date that they do a bit of improv: they would pretend to be long-lost lovers who had met by chance at a pizza joint.

He wasn’t her usual type—older, not very active, not much of a family man—but none of that seemed to matter. She was smitten. “I feel like an adolescent again!” she told me. Soon she and Brian were spending every moment together, going for long weekends to the beach and attending parties with his high-powered Beverly Hills friends. I watched my mother transform again: from Ms. Independent to loyal girlfriend.

My stom­ach dropped as she re­layed this to me over the phone. How could I have en­cour­aged her to make her­self vul­ner­able, to open her heart, when I knew how men had failed her in the past?

Then Brian started having vision problems, and their relationship shifted. Suddenly she found herself driving him across town to doctor’s appointments, cleaning, cooking, organizing his files. Overnight, he had become controlling and insecure—“just like your father,” she confided. But the comparison wasn’t complete until, one weekend at the beach, he left his email account open on her iPad.

Unsuspecting, she logged in and found the unthinkable: other women, dozens of them. She’d fallen for his act.

My stomach dropped as she relayed this to me over the phone. I knew I was supposed to play the role of reassuring romantic confidante. But for the first time, I was at a loss. What could I say that would make up for this? How could I have encouraged her to make herself vulnerable, to open her heart, when I knew how men had failed her in the past? Unable to think of an appropriate response, I suggested, lamely, that she go for a run.

“I think I will,” she said.

My parents split up when I was 3. Soon after, my mother began going on long runs along the canal. I used to wake up early, and catch a glimpse of her slipping out the front door, her slim frame silhouetted against the first magenta rays of sunrise. When I came downstairs an hour later, she’d be in the kitchen, making coffee. She looked as if she’d just won a battle.

Why did she do it, day after day? I wondered. What invisible force was propelling her forward?

Later she started taking me with her, and I understood. Running, for her, was a test of will. On the road it was just her, heart in her chest, her footfalls pounding a steady metronome along the miles of concrete that led to the beach. Like dating, running was a coming-to-terms, a private reckoning. A reminder that, at the end of the day, you always come home to yourself: flawed and imperfect, with all your triumphs and failures, your strengths and limitations, your mistakes and painful memories. What matters, in the end, is that you keep moving.

After Brian, my mother stayed in motion. She took a break from online dating, canceled accounts, deleted phone numbers. She got back to seeing her girlfriends, doing yoga, picking up the pieces she’d lost.

Gradually, her lightness returned. Soon she had enough flippancy about the situation for the both of us. Brian was no longer her crushing defeat, but merely one of a series of dating stories that I (she informed me) would someday write down in a book. A few months after the event, she called to tell me that he’d left yet another voicemail on her phone, which she had, of course, promptly deleted. “Are you taking notes?” she asked. “People have to know!” Then she laughed wryly. “Hey, at least I didn’t marry him.”

The next week she was back online, fishing.

One in a series of personal Perspectives. We invite readers to submit their own essays—inspiration can come from CALIFORNIA magazine or CALIFORNIA Online stories, the news, issues of the day, or campus life. Read more:

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