“Have you ever fallen for someone you weren’t initially attracted to?” asks a large laminated flashcard in the center of a tastefully distressed wood table. The table is in the back corner of the “music room” of the SoHo House member’s club, itself located in a fashionably distressed brick building hidden away in Southeast Portland. Half a dozen fashionable socialites gather around the card and consider its implications. Isn’t attraction where you find it? Are we talking about falling in love or in lust? What even counts as “attractive” these days? The two dudes at the table in expensively discrete heavyweight T-shirts venture some thoughts. Five or six women, dressed in a mix of evening and athleisure wear, share their own experiences with this particular scenario.

I’m at The Group Chat, a sort of roving social club operated by a duo of Portland-based sex educators on a quest to get people out of the house and into thought-provoking discussions. The duo, Kelsey Peake and Tessah Joseph, operate as Squirm, an umbrella organization for their Porn Nerds podcast, a calendar of meetup events, and card deck of sexy conversation starters, which includes many of the prompts adorning the tables at their events. Their events hop from bar to bar (and even a sex club or two) over the course of a given month.

Peake and Joseph started Squirm four years ago. “It was a pandemic project for us,” Peake says, with the aim to produce some online resources “de-stigmatizing the topic of sex and sexuality.” That took the form of virtual workshops and audio sex ed guides. When the pair reunited in Portland after the lockdown years, they decided to get physical: "We were like, ‘oh we can do events now. We can get people in the same room,’" Joseph explains.

While Squirm has experimented with designated speed dating events in the past, meetups like Group Chat are more about discussing sex and/or relationships rather than acquiring sex and/or relationships. True to the sex ed origins, the Squirm outings feel like a cross between recreational group therapy and a thought-provoking Savage Love column. Indeed, Peake and Joseph have regularly hosted afterparties for Savage’s HUMP! pornographic film festival, which should give you an idea of the tone: lighthearted and sexy with a strong focus on consent and good communication. “[It’s] not quite a dating event specifically, but definitely with the themes of sex and dating and relationships,” Peake says in between rounds of structured conversation. 

Peake and Joseph say they aren’t anti-speed dating or singles nights, but they want to give people more leeway to explore. “It’s real open season to talk to people, but there’s no expectations,” Peake says. To that end, they’ve developed a "squirmy scale” to indicate the type of content each type of event is likely to cover: Group Chats are Squirm Level 1, which translates to “slightly spicy icebreaker questions,” whereas Game Night at downtown sex club Sanctuary is “Squirmy Level +++” and gets a bit more involved, they say. “There’s some nudity and some physical touch,” Joseph explains, but adds that it’s still pretty tame by sex club terms. “It’s like, ‘Let’s play Jenga and spank each other,’” she says.

Twenty blocks away, at the clubby ‘70s styled bar Sugar Hill on Southeast Belmont, another group is rapidly assembling. A beachhead by the door has been established by a squadron of bubbly greeters, anchored around event organizer Tiffany Hollon. Hollon is youthful, outgoing, and exudes the confidence of a natural matchmaker. Her group, Meeting Mutuals, began as an attempt to mash her own friend groups together. 

“My first entrepreneurial venture was professional organizing, light interior decorating, that sort of thing,” she says, which occasionally extended to organizing people. “I started to throw these parties where you come and bring a friend that you’d love to introduce to other people, whether or not they’re single. There’s not a specific topic in mind, it’s just a third space.” 

Portland social groups are notoriously cliquey, and for a sociable transplant like Hollon it seemed like there was room to innovate. “Texas is known for its friendly people,” she says with a faint, but unmistakable twang. “When you go to a bar in Austin, it's just party time, right? People are there to meet new people. They're like mixing and mingling.” Anyone who’s walked into a Portland bar and found everyone studiously looking at their phones or tucked away in private booths will recognize that’s not always the case. “I didn't really quite see that [openness] here, and that was such an important part of my life [in Texas],” Hollon says, so she decided to do something about it. 

Meeting Mutuals has expanded in two directions: there are the entry level Delete the Apps public meetups, as well as members-only dinners with a more curated focus. The meetups, like the one at Sugar Hill, are deliberately unstructured: no icebreakers, no prompts, no polite chimes to move to a different table. “All we do is fill spaces,” says Victoria Holden, Hollon's business partner who's doing double duty tonight as one of the event's several cheerful greeters.

Participants wear stickers indicating who and what they’re into: pink for girls, blue for boys, a purplish one for either/both, and a big yellow smiley face if you’re just out to make new friends. “We used to have 18 stickers, but we found that four works best,” Holden notes. Many of the folks at Sugar Hill sport a rainbow of preferences, although on balance this crowd skews pretty hetero by Portland standards.

There’s also a pile of larger white stickers filled out with interests like “Travel” and “Hiking,” along with some blank ones and a pile of Sharpies if you’re looking to broadcast some niche interest (“Pizza” is a perennial favorite, says Victoria). This is basically what Meeting Mutuals brings to the table: a bar full of friendly folks with one level of ambiguity removed. No number of stickers can truly reveal the interior of the human heart, but at least this way you can tell from a distance that someone’s into boys and/or girls and/or pizza, and that they’re potentially open to chatting about it. Conversing with strangers in bars can be a fraught exercise in Portland: A lot of folks are reluctant to explore outside the confines of their preexisting social networks, while others simply want to go outside and be left alone. That’s just the Pacific Northwest for you. But everyone here has decided they’re open to new connections, which feels like a start.

The contrast between the two events is striking, but not incompatible. Squirm events are very much for folks with good emotional radar and willingness to discuss potentially intimate subjects with complete strangers. It takes a little getting used to, but in our increasingly cloistered online society it can feel very liberating to dive straight into the deep end with stuff like this. It’s also a good way to examine your preexisting assumptions about what’s “normal” in the bedroom—or the shower, on the coffee table, or one of several public locations it would be inappropriate to divulge here (what’s said in Group Chat stays in Group Chat, after all).

The Meeting Mutuals event, on the other hand, feels more like a bar night with some training wheels. This isn’t a bad thing, especially for a generation of twenty-somethings who didn’t get an opportunity to learn how to make small talk thanks to COIVD, or older folks who got a bit rusty during lockdown. Society often treats social skills as a thing you either have or you don’t, but just like any human behavior, you can get better at relating to people if you put some time and thought in.

The two groups are collaborating for the first time for an event on October 24 at Jackie’s. The hybrid event is described as a “free dating party downstairs and a mixer upstairs,” which should give folks an option to sample both approaches at their leisure. There’s often a stigma attached to stuff like this, singles nights, meetup groups, what have you, but I’m pleased to report that these approaches to getting folks talking are hip, inclusive, and very accessible to the average bar-going adult.

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Delete the Apps (Featuring Squirm), Jackie’s, 930 SE Sandy, Fri Oct 24, more info, free, 21+