Could a six-week friendship ‘boot camp’ in San Francisco cure loneliness? I decided to find out

It began with an Instagram message. 

“Hiiii,” the message from @realrootsgals greeted me cheerfully, with a sparkly heart emoji and a hyperlinked invitation to a women’s wine night. It led to a website picturing gaggles of smiling 20- and 30-something ladies sipping wine, gathered around fire pits at Crissy Field, taking selfies.

RealRoots was a startup that promised to help me “get matched with like-minded women to build meaningful friendships” over six weeks—for a mere $299. 

I filed away the text as a vaguely interesting piece of spam. But I kept thinking about it. The truth was I had been feeling pretty lonely lately.  

It had been two and a half years since I moved to San Francisco from Los Angeles for a job—a life change that was followed by my boyfriend of six years dumping me. I had since dated up a storm, and I was on friendly terms with many of my co-workers, but did they want to get together for Sunday brunch after seeing me all week? 

I felt adrift without a core group of female friends. At 32, I wanted a Miranda, Charlotte and Samantha in my life to listen to my dating adventures and lean on when shit hit the fan. 

I wasn’t alone. In May, the U.S. surgeon general warned that the pandemic and the switch to remote work had fed an epidemic of loneliness that poses health risks as harmful as smoking up to 15 cigarettes a day. Researchers say digital culture has fed a lack of community that has left young people in particular feeling isolated.   

Of course, that hasn’t stopped online apps from turning this widespread sense of isolation among young professionals into an opportunity. Dozens of friendship apps have been around since the 2010s, but companies like Bumble have recently expanded their offerings. Earlier this year, the popular dating app spun off its friend-finding feature, Bumble BFF, into a standalone app.  

But while the internet has—for better or worse—become the de facto path to finding a mate, online friend-making has not taken off in the same way as its romantic counterpart. Now post-pandemic loneliness has driven a growing number of digitally savvy San Franciscans to find inventive ways to fill the gap. A handful have repurposed online community and event platforms like Meetup and Discord to forge friendships via offline gatherings. 

RealRoots is one of several local ventures that have taken that model of intentional IRL friend-making to the next level.  

Dorothy Li, the startup's 37-year-old founder, thinks the problem with online friendship platforms like Bumble BFF is that they require people to spend hours on screens scrolling and chatting with potential matches before they ever even meet—basically, many of the same things people hate about dating apps.

While RealRoots uses technology to target potential customers—I’m among the 11% of people who responded to the company’s DM—it takes things one step further by creating real-life conditions that nurture friendships. This format “works even if you're really busy. It works even if you are too shy to make the first move,” Li said. 

Like many startups, RealRoots was started to solve a problem in Li's own life. At 37, she has moved nine times since graduating from college in 2007, a way of life that’s become increasingly common among young professionals who tend to change jobs and cities every few years. The Stanford Business School grad already had two startups under her belt when she landed back in San Francisco in 2022, but this time, she wasn’t going to let years go by before finding her people. 

“I remember I was on the blogs, ‘Like, how do people in SF make friends? Like, why is SF so lonely?’” Li said. “And there'd be so many people on Reddit and on other blogs, talking about that same problem, that SF is an incredibly lonely city.” 

At Stanford, Li immersed herself in research on human connections, interviewing about 100 people. She found that unlike men, who like to socialize in co-ed situations over activities, women tend to prefer making friends in female-only settings through conversation, “especially meaningful conversation around emotions.” 

Last year, she launched RealRoots, a “boot camp for making friends.” She is launching new chapters in the South Bay and East Bay in the coming weeks and is trying to raise funds.    

The six-week program—whose cost Li recently lowered to $249, not including food and drinks—kicks off with a $20 introductory wine night where you have a chance to meet five to 10 women who might join you in the “boot camp.” Those who opt to go on participate in a month and a half of walking tours, scavenger hunts, happy hours, dinners and one-on-one friend dates with women around their same age. A guided discussion theme about a universal topic, such as dating or family, anchors the gatherings.

If you don’t make at least one friend by the end of your six-week journey, Li offers to rematch you in a new group free of charge—although she says none of the nearly 1,000 women who’ve gone through the program since she started it a little over a year ago have taken her up on that. 

“What are two traits you look for in a friend and why?” asks Cecilia, a paid RealRoots “guide,” who functioned a little bit like a Girl Scout troop leader. Her job was to watch over and encourage the nascent friendships between me and six other 30-something professional women. 

Gathered around a long table at an Italian bistro in NoPa on a late September evening, eight of us had gathered over shared plates of burrata and glasses of wine to articulate what we were seeking in a friendship. The whole thing was a little awkward, like the first day of class. 

Zoe, a native San Franciscan and bartender, had just relocated back to the city after a major breakup and was looking for friends to help her rebuild her life here. 

Caitlin, a flight attendant in her early 30s, said she hoped to find friends who share her strong family values.  

Diana, 36, who went to San Jose State and works for a credit card company, was seated across from me at that first, slightly stilted gathering. She had recently moved back to the Bay Area to be with her girlfriend after spending the better part of a decade in Amsterdam and Berlin. We struck up a little small talk, and I soon learned her star sign—she’s a Cancer—and that she would be my first one-on-one friend date. 

A few days later, Diana and I bonded over Barbarella cocktails at a restaurant on Union Street. 

She sported red lipstick and a leather jacket and had a cool, European vibe à la the second season of White Lotus.

Diana mused over a familiar local theme, how the San Francisco she had known in her early 20s had changed radically. She lamented that her social circle in the city “went from 100 to zero.”   

“I don't think people are as friendly as they used to be,” she said. 

So she decided to give RealRoots a shot. 

“At least it's a way to get me out of the house every week,” she said. 

It turned out that we had a lot in common besides our paltry social lives. We were both Latinas raised by single moms near Los Angeles; we’d both spent time in Berlin and fallen in love with the city. And we shared a love of salsa and bachata dancing and wanted to improve our Spanish. 

Getting ready for bed that night, I fantasized about the possibilities of our friendship. Maybe we could take language classes together or plan a trip to Germany or dance the night away at a local club.   

“I feel like we could be friends!” I gushed into my voice memo diary.

RealRoots isn’t the only Bay Area venture aiming to help people connect in the flesh. 

Rafat Khan likens his new monthly subscription service, Tribe, which launched in June, to a co-ed social club. Membership costs $39 to $69 for access to themed dinners, picnics, concerts and parties. 

Prospective Tribe members have to pass a screening by Khan, who acts as a sort of platonic matchmaker, introducing people at events and suggesting thought-provoking discussion topics.  

Tribe has registered some 150 members in the city—primarily Bay Area residents in their 20s and 30s—and Khan said 700 are on a waitlist. He plans to launch in LA sometime next year.

For those who don’t relish the concept of paying to make friends, there’s City Girls Who Walk San Francisco, which requires no down payment and only your two feet to carry you along the Embarcadero or on a hike in Lands End. Inspired by a national grassroots movement of women taking to the streets to find fellowship in cities from New York to Chicago, the local chapter started after founder Sydni Topper spent a very lonely summer in San Francisco between quarters at Stanford Business School and decided to bring the concept to the Bay Area.   

About five people showed up for the inaugural walk at Fort Mason in June 2022, and the group now has around 5,000 followers combined on Instagram and TikTok, which features videos of women walking en masse through the city. 

Like a lot of great things, another female-focused social group SF Girlies grew out of a breakup. After finding herself suddenly single, 24-year-old tech worker Helen Morris remembers “feeling like a freshman in college again.”

So Morris posted a silly slide show on TikTok in which she and a friend invited local women to join them for a very amateur game of tennis. About 150 racket-toting women showed up to the Alta Plaza Park courts. 

The women-focused group, which lives on the office-oriented instant messaging platform Slack, has since amassed almost 1,800 followers, who use it for everything from advertising picnics and impromptu midday coffee breaks to apartment shares and used vacuums. The group also recently launched an Instagram account called the “SF Women’s Social Club” to publicize its gatherings. 

“I think that everyone just felt this really special feeling of, ‘Oh my God, this is really great that we have this space to connect and make friends,’” said Morris, who as of now has no plans to monetize the endeavor. “If just one person makes a friend, that's just so, so amazing.”

I was pretty sure I had done that by late October, when the RealRoots friendship boot camp ended. I’d giggled over my lack of air hockey skills with Zoe at a bar arcade in NoPa, dug into spoonfuls of paella and the meaning of adult friendship with Lori in the Mission, sought dating advice from Rose in a dark bar on Polk Street and danced the night away with Diana for Dia de los Muertos at the California Academy of Sciences. Instead of sitting home alone on a Friday or Saturday night, I actually went to two house parties, one of which involved throwing together a last-minute Halloween pussycat costume.

The experience was not a cinematic montage of gal palling, but there were a few laughter-filled nights spent competing at arcade games, some dramatic personal confessions and several awkward moments of uncertainty over how we should split the check. 

In short, I think I began some female friendships.   

We even have a spreadsheet for Friendsgiving.