Dating After Divorce: One Local Shares Her First Experience on Dating Apps

Walking into a room full of strangers isn’t high on the fun index for most. It’s inherently awkward: Everyone’s standing in closed-loop clusters, deep in conversation, and, depending on your social aptitude, the feeling is somewhere between light apprehension and burning alive from the inside out. The pull to retreat or reflexively look busy on your phone is stronger than the drink you now deeply crave. Having friends is nice, but making friends can be brutal.

There’s plenty of commentary on the loneliness epidemic. Last year, the American Psychiatric Association reported that one in three adults feel lonely at least once a week; those aged 18 to 34 are more likely to feel isolated and even more likely to turn to social media as a result. Dr. Vivek Murthy’s “My Parting Prescription for America” cautioned that “being socially disconnected increases our risk of heart disease, dementia, depression, anxiety, and premature death.” So it’s not just an emotional need; it’s nearly nutritional—chit-chat and the occasional wine-fueled, emotional deep-dive are just as important as Pilates and a reasonable amount of kale.

Finding social connections in any city is hard, but San Diego has very specific challenges. This is largely a transient population that acts as a temporary hotspot for many and a permanent home for few. Pick your reason: high rent, surreal gas prices, housing shortage, meh job opportunities (ranked 71st in the country in 2025), or the fact that active military is a sizable chunk of us (110,000-ish)—stationed here for a stretch, then gone. This constant flow of departees sucks out the potential for deeply established families and friend groups, leaving a good share of nomads, searchers, and plenty of people feeling socially awkward.

“There’s an underlying loneliness in all of us,” says Ramel Wallace, the host of monthly meetup CreativeMornings. “There are not a lot of San Diegans who are born and raised here, so [even those] San Diegans end up being just as lonely as the person who just got here.”

Every month, in local libraries, breweries, and small businesses, there are ambitious social architects who have made a career out of undoing social sads. Extroverted champions of the awkward and searching, they’ve struck gold on in-person connection.

The first moments in a social situation are crucial. Sets the tone and cools the nerves.

At Pitch-A-Friend, singles recruit their close friends to present a slideshow of their dating green flags. The entry points for connection at Pitch-A-Friend are simple, old tech: stickers. Each colored sticker indicates if the wearer is single or taken, queer or straight, or practicing ethical non-monogamy (in a partnership but open to others under a mutual understanding).

At the helm of each showcase is Arielle Fuller, aka Chief Wingwoman, who is making dating hopeful again. As Fuller explains, this takes some of the fear of rejection out of a first interaction. “Putting a sticker on immediately means, ‘I wanted to leave my house and talk to someone, and I am a safe space to come and speak to me,’” she says.

Of course, not all of San Diego’s events designed to make connections are romantic. On the last Friday of every month, hundreds gather at San Diego Central Library for the local chapter of CreativeMornings—an org formed to unite creatives in various cities across the world (designers, artists, writers, producers, performers, architects, etc.).

These aren’t your standard business card swaps, though. Coming from a hip-hop background, host Wallace uses call-and-response to break the fourth wall. “This is not my stage at all, this is our stage,” he says.

In your standard lecture-based meetup, the crowd silently faces the host and acknowledges nobody except those they came with. At CreativeMornings, everyone is encouraged to look around, pay attention to the strangers in the audience—not just the host. Wallace will pull volunteers to read the CM manifesto aloud, and he passes the mic to creatives, who make 30-second pitches to the community about projects they’re working on—and there’s always an invitation to connect and collaborate with the presenters whose ideas struck a chord.

The U.S. Chamber of Connection (yes it exists) says people experience life transitions nearly every year, and in these stretches are more open to forming new habits, relationships, and communities. In a revolving-door city like ours, the transition often comes when someone moves away. In 2023, the Census Bureau reported San Diego had the ninth-highest rates of domestic out-migration in the US.

This poses an issue for friendships that IRL SD addresses in monthly friend-making events called 619 Night.

“San Diego isn’t a place a lot of people stay forever,” says Alex Hunter, the creator of IRL SD. “They leave, and people [who stay] lose that community, so they’re hungry for community again.”

Their website describes the vibe as “backyard party meets college fair meets networking event meets happy hour.” Each follows a theme—wellness, sports, refresh and reset, etc.—with related community groups joining as well.

“The people I encounter are trying to get a fresh start in some capacity, so they’re more open, receptive, and ready to meet new friends,” Hunter says. “They need the circle.”

Another way adults can break out of this disconnection is to revert in unison, says artist Elisa Summiel-Bey. The 2015-ish adult coloring book moment in the US was based on some real science, with multiple studies finding coloring has a noticeable meditative and stress-release effect by taking the brain away from anxieties and mental inventories, and focusing it on a simple, easy art. Summiel-Bey’s company Illustrated Melanin throws “Color & Chill” events, turning that trend into a group exercise, along with live DJ sets, wellness experts doing sound baths, and food and drink from BIPOC-owned local businesses. “I tend to think of coloring as your way to tap back into your childlike play,” she says. “As adults, I think we’re almost scared to let loose and have that unabashed joy.”

All of these social meetups attract crowds of likeminded connection-seekers, but high attendance is not the only thing that matters. Metrics nuts can track RSVPs, but spreadsheets can’t capture intangible wins: friendships made, innovative ideas sparked, collaborations kicked off. At CreativeMornings, Wallace redefines ROI as Return On Imagination. Resounding success means thoughtful inquiries over coffee, curiosity about the monthly meeting themes, and requests to take the microphone.

A simple, observable ROI is an increased number of window shoppers to the experience—on the periphery, watching from afar, looking for the right way in. Hunter from IRL SD sees the anxiety in her DMs. “The scariest part for you right now is not meeting new friends: It’s the unknown,” she says. “It’s the gap between ‘I’m here’ and ‘That’s where I need to be.’ If I can help you understand, or get a little bit of a shape around that unknown, it’s much more approachable.”

Being able to bridge that gap, however, depends on your ability to step out of your own mind. “It’s not a connection crisis; it’s a courage and confidence crisis,” says Fuller. The first hello could be as easy as, “Hey, cool shirt.” These are the types of things she includes in her confidence lab reels on Instagram and weekly newsletters.

Ever left a social event and shot straight into a spiral? Was I being weird? Why did I tell that story? I hope that person moves to another state very soon.

The experts say that post-event self-interrogation is a standard-issue part of being alive.

“I love awkward people, and I love being awkward myself,” says Wallace. “It’s humbling to experience: ‘I’m not alone. Finally someone is not put together.’ So give yourself that grace.”

Ray’s Tennis doesn’t look like much from the outside. Never has. It’s just a green box with cloudy windows in Hillcrest, just steps away from a McDonald’s on University Avenue. But for nearly 60 years, this place has been the genesis for three generations of San Diego tennis dreams. Head inside, and you enter one of the tennis world’s great cornucopias.

For years, there was a tennis court behind the store, where owner Bob Ray gave countless lessons. It was like a racket-sport speakeasy; most customers didn’t realize the court existed unless Bob or his wife, Hiroko, guided them through the back door of the shop. Eventually they converted it into a half-court indoors—where a patron might take a racket for a few trial thwacks, trying to avoid rounders of tennis clothes that shared the space.

The shop is an abridged living history. Relics hang from the ceiling: a model of an old metal racket used by fiery lefthander Jimmy Connors in his heyday, and a version of the wooden Donnay that Björn Borg wielded on his way to five consecutive Wimbledon championships from 1976 to 1980.

And just inside the front door is Hiroko eternally stringing new rackets, carefully threading and adjusting the tension of the polyester strings, back and forth, until she has the entire racket head strung.

“I worked seven days a week—five days off in the year,” she says. “My hearing is still good. Physically, I’m as good as I was. Working seven days a week, standing all day. I’m mentally healthier than most people.”

The racket stringing is an operation she does up to 20 times a day—and one that, in some ways, resembles the thread work done by her father decades ago, when he ran a tailor’s shop in Japan.

Hiroko, now 81, was born in the city of Yokosuka at the tail end of the WWII. Her family evacuated to the countryside to escape the bombing raids, and she remembers growing up surrounded by rice fields and mountains. It was in Japan that Hiroko met Bob, a third-generation San Diegan, in the late 1960s, when he was stationed there with the Navy.

Among his possessions at the time was a tennis racket. Inherited from his father, who died when Bob was 11, this racket changed the trajectory of his life: He played constantly, filling up his school days, afternoons, and evenings on the tennis court. He was one of the highest-ranked teen players in the state, and he dreamed of joining the international tournament circuit after his stint in the Navy. But—speaking plainly—he acknowledges that he wasn’t quite good enough to compete with the best of the best. So, instead, he modified his dreams. He and Hiroko returned to San Diego in 1968, and he took a job as the club pro at Morley Field. By their mid-20s, in lieu of touring the world on the tennis circuit, the couple was running the club’s tennis store.

They spent 11 years at Morley Field, which at the time was one of the city’s tennis epicenters, hosting major tournaments for juniors. When the city handed over the store lease to a wealthier applicant, the Rays took over the property on University Avenue and moved in their tennis gear. They have been there ever since—through the McEnroe and Navratilova and Evert eras; the rise of Agassi and Sampras and Graf; the reign of the Williams sisters; the Federer-Nadal-Djokovic rivalry; and into the Alcaraz era. In the near-half century they have sold tennis gear in Hillcrest, the Rays became beloved anchors of the neighborhood’s business community, symbols of stability in an ever-changing environment.

At 84, Bob is still lean and, in his Lacoste tracksuit and Adidas cap, remains every bit the club pro. Like Hiroko, he comes to the store every day—though sometimes, if he is playing tennis in the morning, he might arrive a little later.

But time has started to take its toll. His hearing isn’t what it used to be, and the aging process is revealing itself to be true. And much to the disappointment of their loyal clientele, San Diego’s “First Couple of Tennis” is retiring, a milestone that marks the end of an extraordinarily long chapter in the city’s tennis history.

But Ray and Hiroko didn’t sell the building to a developer for condos or to a big-box retailer looking to open a boutique outpost. Determined that Ray’s should remain a tennis temple, they have negotiated a sale to a former employee who wants to continue the Rays’ legacy.

As of this writing, Hiroko and Bob remain in charge, Hiroko stringing rackets, Bob sharing his expertise about new gear. As much as they love what they’ve built, their hope is to move on soon.

For Hiroko, the prospect of retirement is bittersweet. “What am I going to do?” she asks. “Am I going to be ok? I never had a boring life. Always busy. Business first. I’m so involved in the business—because I didn’t want to fail.”

She looks around her store as she continues stringing. For her, the gladiatorial nature of tennis has always been a metaphor for how to succeed in life. “People have to have a drive,” she says. “You can’t just quit because you lose to so-and-so. Tennis players have that mindset.”

She pauses to talk about all the people who have come through the store’s door over the decades, and the relationships she has built with them. “It’s wonderful to have a great customer. That’s probably the reason I lasted this long.”

A wedding is a lot like falling in love and opening a spreadsheet at the same time. It plays out like a Hollywood rom-com, with laughter between kisses, lace samples pinned to vision boards, and a refrigerator overflowing with red velvet and jasmine-infused buttercream cake tastings. Then the invoices arrive.

The good news? Local planners, photographers, and floral-forward creatives agree: A wedding can feel luxurious without an unlimited budget. Top San Diego experts share their most intentional, stylish, and sanity-saving advice on what to skip and what to prioritize.

Close the Bar (Yes, Really)

Stephanie Purciello, lead planner and creative director at Weddings and Events by MP, recommends a counterintuitive money-saver that also elevates the guest experience: briefly closing the bar during key moments like speeches and special dances. “It creates focus, keeps the moment intentional, and naturally reduces alcohol consumption,” she says.

That small pause translates to hundreds, sometimes thousands, in savings while making those moments shine. Or, cutting back on a full open bar in favor of beer, wine, and specialty cocktails creates room for premium spirits and elevated ingredients, like real grapefruit juice in a paloma instead of grapefruit soda.

Save on: Full bar packages
Splurge on: A signature French 75 with the same Champagne from a favorite date

Make Your Florals Work for You

Ceremony florals deserve an encore, Purciello says. Aisle arrangements can greet guests at the reception, the ceremony arch might be re-staged behind the sweetheart table, and pedestal blooms can move to flank the cake or band. Repurposed designs can save couples $1,000 to $5,000 while keeping the day visually cohesive.

But don’t confuse efficiency with cutting corners. Gina Hundley of SD Weddings by Gina reminds couples that florals set the tone. “You’re investing in food, music, photos, everything—and then the bare minimum on flowers? It will show,” she says. She’s not calling for maximalism; just thoughtful, quality blooms that elevate every photo.

Save on: Unnecessary arrangements
Splurge on: Intentional florals that anchor the entire aesthetic

Don’t Sleep on the Veil Hack

Boutique veils can be marked up four to 10 times their wholesale cost, so Purciello suggests either borrowing one from a family member or opting for a handcrafted design from Etsy for around $40. With the chance to personalize, brides can still achieve a timeless—and often more meaningful—look without splurging on tulle. This opens the door to invest in a skilled tailor, giving you a dress that drapes flawlessly and leaves you feeling like a celeb at the Met Gala.

Save on: The veil
Splurge on: Tailoring and fit for the dress itself

Go Digital

Megan May of Megan May Films loves a digital-first approach before the big day: a sleek video save-the-date, a beautifully designed wedding website, and effortless updates via Instagram keep guests informed without a single stamp. Even conventional guest books are making room for innovation, from heartfelt video clips to tearjerking audio messages.

But when it comes to deciding between photography and videography, Hundley keeps it simple: Always choose photography—especially if you’re tempted to split your budget and settle for a cheaper version of both. “Photos are what you frame, gift, post, and treasure,” she says. “Besides a new partner, photos are what you have left when the food is gone and the music stops.”

Save on: Traditional postage and a videographer
Splurge on: Your dream photographer

Minimalist Décor is the Move

“Simple is in,” May says. It’s all about organic accents, long-stem lilies, thrifted candlesticks, and effortless styling. “Splurge on the elements that feel most ‘you’, whether that’s a styled backdrop for a photo booth or handmade matchboxes.” Love color? Real-life still-lifes of whole fruit inexpensively brighten up tablescapes. Linen costs got you down? Hit the thrift store and round up some white tablecloths on the cheap. Minimal doesn’t mean forgettable!

Save on: Elaborate installations or dozens of centerpieces
Splurge on: One styled backdrop for photos or the ceremony

Skip the Favors

Edible favors melt, classic keepsakes like tiny picture frames or decorative knickknacks often get left behind, and packaging costs add up—so, May notes, couples are increasingly skipping traditional parting gifts. Instead, they’re enhancing guests’ day-of experience and sending them off happy and fed with post-dancing midnight snacks. Consider your favorite San Diego sliders; a French fry bar with every sauce imaginable; DIY street tacos; or, yes, even boxes of pizza. Or keep favors simple, personal, and virtually free: ForEvermore Weddings’ Stephany Peterson recalls a bride who wrote a thank-you note for every guest. “It left a lasting impression,” she says.

Save on: Wedding favors
Splurge on: Late-night snacks guests will rave about

Let the Venue Do the Heavy Lifting

Nothing sets the flow and ambiance like the venue. Ricardo Zarate Jr., Fox Point Farms’ general manager, believes it should be every couple’s top investment. A stunning venue may cost a little more upfront, but it saves you on extras like elaborate lighting, backdrops, and décor. Flattering candlelight and Pacific Ocean glimpses make for moments that feel timeless.

Save on: Over-the-top lighting rentals
Splurge on: A venue that inherently shines

One year ago, I ended a relationship that I thought would be my forever. It’s strange to think in those terms, the idea of forever and all that might have happened between us, and all that will never happen now. But to see how much can change and be accomplished in only 365 days, I’m re-writing my concepts of time. I’m imbuing my future with a new kind of depth and richness I never thought possible, and I’m looking forward to what comes next. 

I am writing this over the sparkling pool at my new girlfriend’s apartment. It’s a cool 80 degrees in mid-October. I’m in my bathing suit, grateful to be soaking up the last few drops of San Diego’s wildly extended summer. The person I was last year at this time no longer exists. The ideas I had for my future back then are no longer relevant. In that girl’s place is a person that I am still learning, but who I respect and admire. She’s worked hard, learned how to pick herself up, faced difficult truths, she’s been brave. And so, it’s time to once again embrace change, and bring this column to an end.

Unhinged has been the perfect sandbox to play in, in a time when I needed a safe space, a place to put my thoughts, to connect with people going through their own struggles with love in San Diego. I’m unbelievably grateful to Nicolle for passing the baton, and giving me the opportunity to share my journey, my mistakes, and my musings with you. Dating is messy, vulnerable and exhilarating. It asks you to navigate your own heart and to be deeply curious about other people.

Getting out into the scene again in my mid 30s was terrifying. I had never used dating apps, and I didn’t know how to present myself in this late-stage era of their adoption. Would I be marketable among all of these savvy users? Would I come off as some post-divorce, mid-millennial luddite? At the end of these past eight months, I’ve discovered some truths about dating and wanted to share them below.

Dating in Your 30s is Fun

I found people to be far more compassionate than I expected, and that dating in my 30s is actually a lot more satisfying than dating in my 20s. People are showing up with fascinating stories and lived experiences. They’ve made mistakes and learned from them, and have room for my story and my past mistakes, too. What matters is showing up clear-eyed about the future. I also feel more resilient about dates not working out, or needing constant communication with dates that do. My confidence in myself is bolstering my bravery to put myself out there and risk being bruised. 

Not All Things That Shine Are Bright

I learned how to recognize and call out some of my old patterns, moving past the “shiny” people that at first might have seemed exciting, and challenging myself to look instead for signs of maturity and intentionality from would-be matches. The old me would have been drawn to people who have some flashy story or passion, but as I’ve gotten clear on my patterns, I know that those people make me feel competitive, and are often masking deeper insecurities. Now I’m looking for people who satisfy my core needs and don’t put me on edge.

Red Flag Meters Sometimes Need Re-Tuning

I explored vetting my red flag meter against new circumstances, asking myself to understand the core of my discomfort versus just the person’s behavior on the surface. For instance, I find myself wrestling with my aversion to sports fans. Is it the sports that are the problem? Or am I just not attracted to reckless spending on merch, games and beer? Trusting your gut instincts, reflecting on your dating history, and communicating clearly with your partner about your boundaries can head off troubles before they begin.

Today’s Dater Can Benefit From Centuries-Old Traditions

First date tension? Swiping burnout? Perhaps seeking advice from a seasoned matchmaker could be the next step in finding lasting love. I talked to Sophy Singer of Sophy Love matchmaking about the benefits of seeing a matchmaker who looks at you and your relationship goals from a holistic standpoint, identifying patterns that are stopping you from finding a fulfilling, well-matched relationship. A matchmaker can help you focus on what it is you really want, show up authentically to first dates, and encourage you to move past surface level dealbreakers or checklists like height or education level.

Leaning on Friendships is Essential

I’ve found that sometimes getting out of my own head, and asking other people for advice can be the key to moving forward past my own stumbling blocks or an issue I’m having in my love life. I’ve allowed myself to become very vulnerable with friends that I trust and whose relationships I respect. I’ve been surprised with the ways they have shown up, thinking about my situation with honesty and focus as I’ve moved through heartbreak to rebuilding to new relationships. It’s helped center my friends in my life in a way I’ve never done before, and now I feel that I have an extended family who loves and supports me as I am.

Despite Its Stereotype, San Diego Can Be a Great Place to Date

The great news is that San Diego is an incredible place to date. The city is thriving with people from all over the world, with endless opportunities to find love. We’ve got a fascinating cultural scene, bars and restaurants galore, hiking trails, beaches, parks. Even dating on a budget is easy, so you never have to cross your own boundaries (even financially) to see if that new person could be your person. 

And if you’re sick of the apps, exploring the city alone could be your next opportunity to meet the love of your life.

There is Hope After Heartbreak

Although I have met someone new, I have no idea what the future holds. All I know is that I’m hopeful, and for perhaps the first time in my life, less afraid of the unknown. I now know what I’m capable of, and that if you lead with an open heart, the world can open to you. I also know that I’ve met someone who motivates me to be my best self. She leads by example. She inspires me every day, and I’m excited to see what we can build side by side.

We are all a perpetual work in progress. You or I will never be perfect, and we will never find the perfect match. But love is more interesting than perfection. I’m open to the journey; thanks for walking a small leg of it with me.

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

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At the 1996 Atlanta Summer Olympics, Dane Chapin had a problem. He found himself in possession of tens of thousands of excess Monopoly games, with no plan on how to sell them. What he didn’t know at the time is that this Herculean task would shape the future of his business.

In 1994, Chapin and his sisters started their Carlsbad company, USAopoly, with a two-year license from Hasbro to make city editions of the popular Monopoly board game. “The game is a great canvas,” Chapin remarks. While some aspects of the game are “sacrosanct,” according to Chapin—the four corners, for example—many of the details can be customized to fit a theme.

USAopoly appealed to local customers by including San Diego and La Jolla editions in the original six games it created (alongside New York, San Francisco, Boston, and Atlanta versions). The tokens of the San Diego board included a surfer, a beach cruiser, and a copy of the Union-Tribune. Instead of Park Place or Reading Railroad, players land on the Gaslamp Quarter or the San Diego trolley. But after two years of city-specific boards, the siblings were ready to branch out.

In 1996, Hasbro gave them license to create an Olympic edition of Monopoly to commemorate the Atlanta games. The Olympic Committee had agreed to purchase 20,000 copies, a huge number for USAopoly in those days. They decided to manufacture 35,000, figuring they could sell the extra 15,000 on their own. The games went into production, but the Olympic Committee hadn’t actually sent over a purchase order.

“I finally get the buyer on the phone,” Chapin recounts. “And she says, ‘We’re going to order 90 games.’ Nine-zero. Not 900, not 9,000, not 90,000. Ninety.”

When he reminded her of the initial request for 20,000, she said that the team had changed their mind. “There was no point for me to get angry or get mad at her,” he adds, laughing. “I just had to figure out what I was going to do.”

Chapin landed in Atlanta for press coverage the week before the opening ceremony. “The Olympics are a white-hot deal, and then it’s done,” Chapin explains. “And once it’s done, there’s really no market for all those goods.” So, he shipped 20,000 games to the city. If nothing else, he’d have them on hand to replenish the stock for local stores. But, while Chapin was walking to an interview with an Olympic Monopoly board under his arm, a man stopped him on the street and asked where he bought it. Chapin sold it to him for 20 bucks. A lightbulb went off.

“We’re sitting with a warehouse of 20,000-plus games that need to find a home,” he recalls. Why not get them directly into consumers’ hands? He rented a van, bought a dolly, and got to work. “I spent the next two weeks on the streets of Atlanta, schlepping games,” he says. At the end of those two weeks, all the boards had been sold at $20 apiece.

Hasbro never knew the full story. But the company did notice how successful the Olympic board had been—and it was all the proof it needed to increase USAopoly’s licenses. “That was the inflection point for USAopoly,” Chapin says. “After that, [Hasbro] expanded our purview, our grants, well beyond city editions.”

Chapin and his sisters started to create pop-culture versions of Hasbro games, producing tributes to everything from Harley-Davidson to Metallica to The Simpsons. Now, three decades later, USAopoly (also known as The Op) is on track to sell over seven million games this year. It’s grown into an international family entertainment company that designs original best-sellers like Telestrations and Flip 7 in addition to twists on the Hasbro classics.

Peek in the archives at the Carlsbad offices, and you find shelves jam-packed with a copy of each game the company has produced since its inception, from the Atlanta Olympics Monopoly that changed USAopoly’s fate to Dragon Ball Z chessboards and RuPaul’s Drag Race Clue.

Chapin shows off the original San Diego Monopoly, still sealed in its packaging. “Think about some of your fondest memories in life,” he instructs. “My fondest memories include going to my grandparents’ house with my brother when I was 10 years old—we’d have a sleepover and play canasta for hours. Talk about joy, laughter, and lifetime memories.” He smiles. “So, that’s my job—to create games that will do that, that will bring people together and get them to put their phones away. It’s pure, and people can be present. That’s more important than ever.”