How Chicago singles are escaping dating app ‘trenches’

Sitting at a Logan Square coffee shop last month, Penny Gibbons hid her face from a man ordering at the counter.

With a nervous laugh, she explained why she was avoiding him.

“He actually ghosted me a couple years ago,” Gibbons said.

Ironically, Gibbons was there to tell a reporter about her journey from disappointed dater to founder of Meet IRL, a group designed for Chicago singles to meet in person. Her experience with the man at the counter and other dating app matches drove her to found the group and break away from the online dating scene some Chicago singles have called “the trenches” and “a hellscape.”

Through Meet IRL, Gibbons plans several speed-dating events, mixers and parties for singles each month. Other groups, including Hot Potato Hearts, Vouched dating events and a Facebook group for singles who love pickleball, have cropped up in Chicago in the last few years as a rebellion against the swipe-forward strategy that has dominated the dating scene for years.

“So many people are over the apps and in need of a service like this,” said Gibbons, 36. “I can’t promise that you’ll meet the love of your life, but I can promise I’ll get a great group of people together and you can try.”

Why are some Chicagoans over swiping?

During COVID-19 quarantines, people were forced to reckon with their relationships, socialization and technology, according to Alexandra Solomon, a licensed clinical psychologist, Northwestern University professor and host of the podcast “Reimagining Love.”

Dating life in Chicago may be permanently altered by the pandemic.

Industry giant Tinder reported its paying users fell by 8% in 2023. Meanwhile, Eventbrite reported a 42% increase in Valentine’s Day singles events in 2024 versus 2023, surpassing even pre-pandemic figures.

“It’s gonna stick around,” Solomon said. “We’ve crossed a really cool threshold that is about people really understanding how essential human relationships are.”

Avondale resident Megan Moran, 32, was left depleted after months of dating through apps. She grew tired of hitting brick walls and dead-end conversations.

“How do I curate a snapshot of myself that feels authentic but is also brief?” she said.

While people can create dating app profiles on a whim, an event that takes effort can “weed out” people who aren’t serious about dating, Solomon said.

The ease of the apps has led to a “gamified” experience, said Lincoln Square resident Alice D’Orlando. Swiping on people can become a twisted competition with oneself, and matching with new people is its own form of scoring. D’Orlando said she became one of the players.

“At a certain point, I was using them just for fun,” D’Orlando, 29, said. “It was kind of a buzz to match with someone.”

But in-person groups require more buy-in. To register for the events, daters fill out a form with questions relating to sexuality, religion, therapy and other specifics.

“It prompts you to think about what you’re looking for,” Monika Wasshausen, 31, said. “It asked the right questions and the things that had been on my mind.”

D’Orlando met Wasshausen, who lives in Uptown, at a queer speed-dating event Meet IRL held last year. They’ve been partners ever since.

Moran, looking for similar buy-in, ditched the apps and attended a Meet IRL mixer at Guild Row in Avondale last year. The event “had middle-school dance vibes,” Moran said.

Women and men separated themselves, nervous to approach each other. But excited tension and anticipation filled the room, a physical buzz an app can’t replicate.

“I see it as a way to cut through the noise to see if there’s chemistry or a spark, that intangible thing that you can’t get from app dating,” she said.

After the mixer, she tried a speed-dating event in March at the Lone Owl in Wicker Park for more structure. And good thing she did — Moran met her boyfriend.

Queer dating and LGBTQ+ spaces

For many queer people in Chicago, a dedicated space is invaluable when dating, said Katie Conway, founder of Hot Potato Hearts, a group that focuses on queer dating events that launched in 2021.

“Sometimes you just want to be with people you don’t want to explain your mindset to,” Conway said.

D’Orlando and Wasshausen lauded queer dating events for carving out a place for female and nonbinary people to socialize, even if a romantic sparks don’t fly. Bars geared toward gay men are much more popular, but groups for queer people of other genders are important, too, they said.

“It was kind of refreshing,” D’Orlando said. “It feels fresh and kind of outside of the scene because we were at this intentional dating space.”

The events can allow people to ease into the dating experience without as much of a guard up and try out different types of relationships, Conway and Solomon said.

“We can talk about Chicago as a progressive city, but having a marginalized identity, for example being queer, there’s a need to know that we can safely be in this space,” Solomon said.

A safer way to meet strangers?

The idea of safety is important for daters across Chicago, especially women, who have long been disproportionately targeted for sexual violence. Lake View resident Sarah Chan, 25, heard dating horror stories and started Vouched dating events last summer, aimed at stemming women’s concerns. Hundreds of daters have attended Chan’s events, where women apply on behalf of men they’ve given their stamp of approval to.

“I’ve never heard a guy be scared for his physical safety,” Chan said. “Maybe he’d be nervous about getting catfished, but that’s not as bad as being murdered.”

A 2022 study by Brigham Young University researchers found 14% of sexual assaults studied in Utah between 2017 and 2020 occurred during a dating app meetup.

“In a dating app, people can shape themselves however they want to appeal to vulnerable victims,” researcher Julie Valentine said in an article about the study.

At Chan’s events, women are able to relax knowing the men have been “vetted” by a woman, she said .

“Having female friends is an important factor to a lot of my friends when dating,” she said. “A lot of guys who only have male friends, it’s kind of a red flag.”

Dating events can foster friendships, too

Singles are also striving for partners and a community that shares common hobbies or interests. Jason Webb, who coaches at pickleball facility SPF in Lincoln Park, has yet to see relationships sprout from his Facebook group, which he started in 2022 and named “Chicago Pickleball: Single & Mingle — No married or committed peeps.” But he’s seen countless friendships take shape.

“Friendships can evolve into relationships,” Webb said.

When dating, Webb, 55, keeps in mind that playing pickleball is a non-negotiable for his potential partner, and he could find someone through his group. The common interest not only prompts a conversation but introduces healthy competition to the dating experience, he said.

“I just wanted to bring people together, and if I met somebody, that would be a fringe benefit,” he said.

Conway and Gibbons said they admire friendships that budded through their groups just as much as any dates or relationships.

“Yes, I’ve gone on some dates; yes, I’ve had some kisses,” Conway said. “But I have new loves of my life in friendship, and that’s even better than anything else.”