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Unhinged, A Dating Series: 20 Years Later, We’re Still Single

Nothing and everything has changed in the dating scene in San Diego in the past two decades—and we still don’t know what we’re doing
San Diego Magazine cover 2005 focused on dating in San Diego

A woman’s bare legs stretch across the page. She’s in bed reading The Union-Tribune, dressed in what appears to be a man’s white button-up. Emblazoned over one bent knee are the words “SINGLE IN THE CITY.”

In other words, San Diego Magazine’s November 2005 cover is wild. And inside waits a huge feature on dating in SD. I had questions. So many questions. Is anything different about SD’s dating scene nearly 20 years later?

“If there are plenty of fish in the sea, why haven’t you hooked one?” the article’s subhead asks. “A look at the up-and-down dating life of San Diegans—and how to make the perfect catch. Maybe.” 

Writer Amber Cyphers goes on to wonder, “With one million people in the city, why is it still so hard to find love?”

This sounds familiar.

“We asked a group of very dateable San Diegans for their take on the world of singles, and did some research of our own,” Cyphers writes. “It was illuminating, to say the least, although there was no consensus on the best way to meet other singles in San Diego. Not surprisingly, few found much success developing lasting relationships with people they met in bars. Beyond that, it was a tossup.”

This could have been written today. I am Cyphers, and she is me. We’ve come so far since the dating-app-free world of yesteryear… while also seemingly going nowhere at all. Great news for singles.

The Old Globe theater a popular spot for singles dating in San Diego
Courtesy of The Old Globe

Luckily, the piece offers some tips about where to meet local singles. Cyphers suggests checking out social events hosted by arts institutions like The Old Globe, returning to school to take extension courses (this seems a bit much), frequenting your neighborhood coffee shop to find “local delights” posted on its notice boards, and getting into sports. 

Did you know there was once an Athletic Singles Association? Or an org called the Single Sierrans, a subgroup of the local Sierra Club, an environmental protection organization, for people in their 20s and 30s? 

Back then, online dating was relegated to sites like or—which may have been the prototype for Tinder, though I can’t be sure.

Instead of my typical article this week, we’re going back in time to hear the stories of other singles looking for love. Because look, it’s not you—it really is that hard and weird and confusing. Grab a glass of wine and some popcorn and get cozy with the tales of San Diego’s most eligible Y2K bachelors and bachelorettes.

Also, if you’re one of the singles profiled in this feature, please email us and let us know if you found love… especially if it was because you went back to college.

San Diego Magazine dating advice column for singles from 2005

Meet Justin, a 28-year-old Oklahoman who discovered why San Diego is such a great place for burgeoning Peter Pans

On the next page, Lisa Feinstein, a 35-year-old healthcare professional, shares her dating horror stories. Offering to find your date a sugar daddy—totally wack or kinda chivalrous in this economy? You decide. 

San Diego Magazine dating advice column for singles from 2005

Here we have 35-year-old Summer Morse, who offers some sound advice and an optimistic outlook for singles. “I’m looking for a relationship full of integrity and communication—having the understanding that falling in and out of love happens, and it’s okay,” she says.

Travis Bone, on the other hand, found that a little wine with a side of pretension is a good reminder that being single may not be so bad after all. 

San Diego Magazine dating advice column for singles from 2005

Tom Chambers’ story might be my favorite of the bunch. A tale as old as time: You and your situationship decide to take separate trips for New Year’s Eve. You head to Lake Tahoe; she jets off to Miami. A week later, you turn on the Lakers game and see her courtside… with another dude. Ouch. 

A holistic healthcare practitioner and divorcée, 46-year-old Lilia Gudiño-Vazquez is perfectly fine with her relationship status. The single mom of two reminds us that dating in your 40s means you’re no longer comfortable wasting your time with things that don’t add value to your life.

San Diego Magazine dating advice column for singles from 2005

At 48, executive assistant Lisa Schiff signed up for what she called “on-line personals.” She’s excited about the idea of a younger man, unless he wants children. How very Anne Hathaway in The Idea of You

Finally, 28-year-old Nam Chantepie offers a cute metaphor about the dating pool. “Sometimes I feel like there needs to be more chlorine in that pool, but I keep floating along in my water wings, waiting to bump into someone else who wants to play Marco Polo,” he says. I genuinely hope he found his mermaid.

So, if you’re single, is there comfort knowing that dating in SD has always been challenging? Or did you find love here decades ago—and think that you left the market when things were easier? Either way, we would love to hear from you. Email us at [email protected].

If you’re new to Unhinged, catch up on all the dating chats you’ve missed here and follow along at @monicles and @sandiegomag on Instagram to know when a new article drops each week.

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By Nicolle Monico

Nicolle Monico is an award-winning writer and the managing digital editor for San Diego Magazine with more than 15 years of experience in media including Outside Run, JustLuxe and The San Francisco Chronicle.

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