Real-life singles help Chicagoans escape the hassles of dating apps

While sitting in a Logan Square café last month, Penny Gibbons hid her face from a man ordering food at the counter.

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

“He actually cheated on me two years ago,” Gibbons said.

Ironically, Gibbons was there to tell a reporter about her journey from frustrating dating to the founder of Meet IRL, a group designed to meet Chicago singles in person. Her experiences with The Man at the Table and other dating app matches led her to found the group and move away from an online dating scene that some Chicago singles called “the trenches” and “the hellscape.”

Through Meet IRL, Gibbons plans several speed dating events, mixers and parties for singles each month. Other groups — including Hot Potato Hearts, Verified Dating Events, and a Facebook group for singles who like baseball — have sprung up in Chicago in the past few years as a rebellion against the swipe-forward strategy that has dominated the dating scene for years.

“A lot of people use apps and need a service like this,” said Gibbons, 36. “I can't promise you'll meet the love of your life, but I can promise you'll get a great group of people together and you can try.”

Why do some Chicagoans hit so much?

During the coronavirus quarantine, people have been forced to reckon with their relationships, social connection, and technology, according to Alexandra Solomon, a licensed clinical psychologist, professor at Northwestern University, and host of the podcast Reimagining Love.

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

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

“It will continue,” Solomon said. “We have crossed a really wonderful threshold in terms of people understanding how important human relationships are.”

Avondale resident Megan Moran, 32, was left exhausted after months of dating on apps. I'm tired of running into brick walls and endless conversations.

“How can I organize a shot of myself that looks real but is also brief?” she said.

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

Lincoln Square resident Alice Dorlando said the ease of the apps led to a “gaming” experience. Hitting on people can become a twisted competition with oneself, and matching up with new people is a special form of scoring. Dorlando said she became one of the players.

“At a certain point, I was just using it for fun,” Dorlando, 29, said. “It was kind of a hype to get along with someone.”

But personal collections require more support. To register for events, daters fill out a form with questions about gender, religion, treatment and other details.

“It forces you to think about what you're looking for,” said Monica Washausen, 31. “She asked the right questions and the things I had in mind.”

Dorlando met Washausen, who lives in Uptown, at a quirky IRL speed dating event last year. They have been partners ever since.

Moran, who was looking for a similar engagement, ditched the apps and attended a Meet IRL on Guild Row in Avondale last year. The event “had a middle school dance vibe,” Moran said.

The women and men were separated from each other, nervous about getting close to each other. But tension and excited anticipation filled the room, a physical buzz that the app couldn't replicate.

“I see it as a way to cut through the hype and see if there's chemistry or a spark, that intangible thing you can't get from dating on apps,” she said.

After the mixer, I tried a speed dating event in March at Lone Owl in Wicker Park to get more organized. The good thing she did was that Moran met her boyfriend.

Gay dating and LGBTQ+ spaces

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

“Sometimes, you just want to be with people you don't want to explain your way of thinking to,” Conway said.

Dorlando and Washausen praised queer dating events for providing a place for females and non-binary people to socialize, even if romantic sparks don't fly. Bars specifically for gay men are more popular, but groups of gay people of other races are also important, they said.

“It was kind of refreshing,” Dorlando said. “It feels new and out of the way because we've been in this intentional dating space.”

Conway and Solomon said the events can allow people to enjoy the dating experience without putting up as much guarding and experimenting with different types of relationships.

“We can talk about Chicago as a progressive city, but having a marginalized identity, for example being gay, there is a need to know that we can be safe in that space,” Solomon said.

A safer way to meet strangers?

The idea of ​​safety is important to people across Chicago, especially women, who have long been disproportionately targeted by sexual violence. Lakeview resident Sarah Chan, 25, had heard horror stories about dating and started dating events last summer, aimed at allaying women's fears. Hundreds of people attended Chan events, where women perform on behalf of the men they have given their seal of approval.

“I've never heard a man fear for his physical safety,” Chan said. “Maybe he'll be nervous about being hunted, but it's not as bad as being killed.”

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

“On a dating app, people can shape themselves the way they want to attract vulnerable victims,” researcher Julie Valentin said in an article about the study.

At Chan's events, women can relax knowing the men have been “checked out” by a woman, Chan said.

“Having girlfriends is an important factor for a lot of my friends when dating,” she said. “A lot of guys have only male friends, that's kind of a red flag.”

Dating events can foster friendships, too

Singles also seek partners and a community who share common hobbies or interests. Jason Webb, who coaches at the SPF pickleball facility in Lincoln Park, has yet to see relationships emerge from his Facebook group, which he started in 2022 and called “Chicago Pickleball: Singles & Mixed — No Married or Committed.” But he saw countless friendships forming.

“Friendships can develop into relationships,” Webb said.

When dating, Webb, 55, keeps in mind that playing baseball is non-negotiable for his potential partner, and he can find someone through his group. He said common interest not only stimulates conversation, but introduces healthy competition into the dating experience.

“I just wanted to bring people together, and if I met someone, it would be an added benefit,” he said.

Conway and Gibbons say they admire the friendships that have developed through their groups as much as any dates or relationships.

“Yes, I've gone on some dates; “Yes, I got some kisses,” Conway said. “But I have a new love in my life in friendship, and that's better than anything else.”