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Photograph: Courtesy of VHS

Chicagoans are revamping speed dating (and speed friending) at these new events

Stuck in post-quarantine loneliness? Try these riffs on classic speed dating events.

Lindsay Eanet
Written by
Lindsay Eanet

A goofy game show where lucky singles can win a date at a favorite local venue. An evening at a bar where your bestie can hype you up to potential matches with a glowing slide-deck presentation. An opening meditation and affirmations session followed by rounds of deep-diving questions ranging from the silly to the weighty. 

In the wake of the loneliness of pandemic isolation and an ever-increasing reliance on dating apps, event organizers in Chicago are creating new evolutions of the classic speed dating event to foster authentic IRL human connections, both platonic and romantic. 

The importance of making spaces for genuine connection hits home for Candis Oakley, who lost her aunt to suicide. “She is the biggest reason why I am passionate about bringing people together and why I believe community care is extremely important,” she says. That ethos led Oakley, a yoga instructor, business owner and marketer, to launch Very Human Social, a “mission driven social club” that produces workshops and events focused on authentic human connection and growth. As a yoga instructor, Oakley says there were always elements of growth and community-building in her class, and the aspect that brought her the most joy was seeing people ask questions and build relationships outside the studio. 

Oakley is encouraging those genuine connections through one of Very Human Social’s signature events, Friend Request. A typical Friend Request evening starts with introductions, followed by time to “get into our bodies” and a brief meditation. Candis shares the affirmations that ground the event and encourage self-trust — “I am present. I am listening. I am safe.” — and then participants begin a series of 10 conversations with 10 different people based on 10 prompt questions. The questions start off thought-provoking but still a little silly:  “If you were arrested with little to no explanation, what would your friends and family assume you had done?” From there, they gradually go deeper: “What’s something you’re sure you’d never do but secretly wish you had the guts to do?” “In what areas of your life do you feel you have a hard time telling the truth?”

“At the last event, a group of people decided they were going to get tacos and drinks together after,” Oakley says. “I try to do it in the happy hour time to encourage people to leave together and continue connecting.”

People chat in a circle at a recent Very Human Social Friend Request event
Photograph: Tajah WareVery Human Social Friend Request

Often, these events are driven by the organizers' own desire for an alternative to dating apps. Court•Ship founder Meghan Griffith was getting frustrated with the oversaturation and lack of movement beyond back-and-forth messaging on the apps. She and her friends talked about the potential of vouched dating—after all, who can speak to why you’re dateable better than your friends? 

Enter Court•Ship’s first event, Date My Friend, where you can not only look for love but test your friendships by pitching your bestie to a room full of singles. “I think it says the kind of friend that you are and the company you keep that you trust someone so much to not only tell people why I’m awesome, but also do an unfiltered Q&A, where you’re able to say this is what I’m passionate about and this is what matters to me,” Griffith says.

To get presenters started, the Court•Ship team offers a Google Slides template with prompts, everything from Myers-Briggs Personality type to your favorite story about the dater, all with time for an audience Q&A at the end. Griffith says the creative process encourages potential daters and their friends to be intentional: “You actually have to sit down and think about who am I looking for? What does it mean for me to be a partner?” 

Griffith says the vibe of the evening is meant to be positive and not take itself too seriously–except when it comes to safety and consent. Date My Friend is open to daters of all genders and sexual orientations, and any form of discriminatory language or behavior is prohibited. 

Like Griffith, Katie Conway began Hot Potato Hearts, her inclusive speed-dating event series, out of her own desire to meet like-minded people in a new way, especially in the wake of the isolation of the ongoing Covid-19 pandemic. “I’m a very social person, so I missed having interactions, and every time I’d go to a bar and strangers would try to talk to me, I would feel very guarded because I didn’t know if they were vaccinated or where they were on social issues,” she says. “I really wanted to create an intentional space for like-minded people to feel safe, whether that meant feeling safe in that everyone was vaccinated or they were LGBTQ+ friendly.”

People sit at tables and chat at a recent Hot Potato Hearts event
Photograph: Courtesy of Hot Potato HeartsHot Potato Hearts

She began cold emailing her favorite bars asking to host speed dating events, and Hot Potato Hearts was born, and with it, a strong following of regulars.

Once Hot Potato Hearts took off, Conway wanted to add a performance element to the show. She collaborated with comedian Kenya Elan to create Perfect Mash, a live dating game show now hosted monthly at Schubas Tavern. The three lucky contestants are selected before the show, and Conway does pre-interviews with them to find out what they’re looking for. When the audience arrives, a QR code takes them to a compatibility quiz. After some time to loosen up with trivia and games, Conway brings the three most compatible people for each contestant, asks them two or three questions and the contestant chooses who they want to go on a date with before sending them off privately to have a drink and chat. 

You could leave with a new concert buddy or someone to do puzzles with on Sundays, or you could leave with someone you date and you get engaged to.

“It’s really goofy and really lighthearted,” Conway says. “We don’t take ourselves too seriously. It’s just about finding someone in a nontraditional way and then going on a date, and maybe you see that person again and maybe you have a really good story or maybe they become your friend.”

Hot Potato Hearts and Perfect Mash are open to people of all genders and sexual orientations, single or partnered and ethically non-monogamous, and everyone is committed to creating an environment where they can authentically engage with each other. To honor guest safety and privacy, matches are anonymous—guests are given name tags at the beginning of the event, and if they like someone they met, they write the name on the inside of their name card. Matches must be mutual for Conway to share any contact information. 

Conway emphasizes that these events are not just for building romantic connections, but platonic as well. “You could leave with a new concert buddy or someone to do puzzles with on Sundays, or you could leave with someone you date and you get engaged to,” Conway says. 

All three organizers stressed the importance of going into these events with an open mind and a willingness to engage, and even get a little vulnerable. “People will reach out to me before and tell me that they’re anxious in social settings and want the rundown of the night,” Conway says. “Speed dating and talking to 15 to 30 strangers in a night can seem overwhelming. But once you get there and recognize there's a pattern and a rhythm to it, and you’re only talking to each person for five minutes, it becomes a lot easier to handle.” 

There are a lot of essential considerations when putting together an event for strangers to build connections, including creating an atmosphere where people feel welcome enough to open up. Oakley says every aspect of the event, from engaging with the staff at the venue to the background music, is focused on intentionality and making everyone feel safe and excited to be there. “I use a lot of disco and new wave to give the feeling of nostalgia, that longing that we’re all looking for,” Oakley says. “I want to create a sense of joy.” 

Although the schedule for 2023 is still being finalized, Oakley says Friend Request will run quarterly beginning in January, and she hopes to start touring with some events and programs. On January 20, she’s launching Heartbreak Hotel, an event centered on how people connect through loss. 

Conway is also branching out her programming beyond speed dating and Perfect Mash with other community-focused meetups. Earlier this month, she launched Book Spuds, a bi-monthly book club open to all, single or partnered, and focused on queer stories. And there’s power, she says, in these open-to-all community-building events, like the bowling mixer she hosted in the spring. 

“I had someone come up to me and tell me this was only the second time that she had come out in public fully identifying as a woman, and that brought me a lot of pride that someone could be their full, authentic self at this event,” Conway says. “I didn’t realize how big of a moment it could be for someone else.”

The next Hot Potato Hearts takes place Tuesday, December 13 at 8pm at California Clipper, 1002 N California Ave. Tickets are $10 and available here. Proof of Covid-19 vaccination is required to attend. The next Perfect Mash will be Wednesday, December 21 at Schubas Tavern, 3159 N Southport Ave. Tickets will be available this Friday. 

UPDATE (December 8): The first installment of Court•Ship Presents: Date My Friend has been canceled. To keep track of other Date My Friend events, visit Court•Ship’s website.

For more information about the next Friend Request and other events from Very Human Social, join their mailing list

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