The Scoop: The COVID-19 pandemic has been a challenging time for professional matchmakers. Stef Safran, who runs the Stef and the City matchmaking and dating coaching firm in Chicago, said the pandemic impacted her business and her clients in ways she had never seen. Since the pandemic has forced people to actually have conversations over video and the phone, singles have found that they need to have better ways to communicate.  After many singles no longer had workplaces to get some automatic watercooler socialization, they craved connection but realized certain questions about health and safety were essential before meeting someone these days. The pandemic changed daily life in cities around the U.S., and Stef said she helps singles in Chicago feel comfortable while finding love.

Stef Safran, Owner of the Stef and the City matchmaking and dating coaching firm in Chicago, knows the COVID-19 pandemic has been hard on singles of all ages. It’s also presented an opportunity for people interested in dating to refine their communication skills and focus on what’s most important: news connections, thriving friendships, and dating success.

The safety precautions and social distancing mandates associated with the pandemic vary throughout the U.S. Stef’s parents, who are retired and live in Florida during the winter months, told her that they felt everything was fine. Their social lives were not highly impacted as they already lived in a retirement community.

Stef is a member of the Matchmaking Alliance, and she connected with several Matchmakers who are located in New York saw most businesses, Broadway, and restaurants shut down. In March 2020, she noticed a lot of mixed messages in her home state of Illinois — especially when she was taking her child to her daycare which was run out of headquarters in Tennessee and Texas. These states have lax policies regarding the pandemic.

Photo of Stef and the City Owner Stef Safran
Stef Safran, Owner of the Stef and the City, spoke with us about how the pandemic changed dating trends.

“I have a physical office, and I also was meeting people in various Starbucks at times. Then the office shut down to redo the HVAC system. Then we were on a ‘stay at home order’ — which was a strange situation to be in,” Stef told us. “The daycare would send notices daily that we were not shutting down until two weeks later when they were required to shut down until they got emergency permission to remain open.”

Stef decided to pull her child out of daycare and set up a home office to check in with clients remotely. While many of her coaching clients have continued to work with her, other singles put dating on the backburner as they wait for vaccination rates to improve and infections to decrease.

Stef said that this is a wonderful time for clients to work on themselves, even if they aren’t in a position to meet a potential partner at a bar or restaurant for a first date. Stef has found more people than ever before are interested in dating coaching. Some want to feel safer in an unsafe time, and others hope to find a love connection with other singles since they are missing connecting with coworkers in the office. 

“With life you have to be flexible and be prepared. This is a good example of how dating really does work. And the people who are more coachable and more dateable are willing to understand and take a more relaxed attitude,” Stef said. “Look at the reality of life right now. None of us control this. Clients often ask when this will be over, and I’ll say, ‘Where’s my crystal ball?’”

Communication Skills Improved During the Pandemic

Stef said she always had difficulty encouraging her coaching and matchmaking clients to talk on the phone before meeting in person. Now, more people recognize the importance of finding a connection before taking the next step.

“I can’t tell you how often I would tell people, ‘You have to talk on the phone, you can’t sit and text,’ and they wouldn’t listen until now,” Stef said. “People are starved for attention and have to ask questions about safety and other things they haven’t asked in the past because they felt it was too much.”

Illustration of Stef and the City Owner Stef Safran
Stef Safran aims to help singles in Chicago find love through her matchmaking and dating services.

Stef said the singles she works with have started getting better about communicating and upholding their boundaries. For example, they may no longer feel comfortable kissing on the first date, and that’s a conversation that needs to be had before the time comes.

The reality of previous generations, or even peers who met their spouses in college, isn’t the same reality today’s singles face. “Even Prince Harry married a woman who was previously married,” Stef said.

Dating remains confusing for many people, especially those who have gotten separated or divorced during the pandemic and find themselves navigating the dating scene for the first time in years.

“If you’re not having any luck on dating apps, the COVID-19 situation just made it worse, and people got frustrated,” she said. “People who haven’t had that social connection or don’t have kids, they’re not as personally connected to why people are not choosing to actively date. A lot of people come across as flaky when it’s really that they suddenly get scared for their health. They’re disconnected from what’s going on.”

That’s why it’s so empowering to work with a matchmaker and coach like Stef, who provides advice and insight on people she knows and has already vetted. Throughout her career, she has worked with singles of all ages and preferences.

Singles Shouldn’t Take Things So Personally

One of Stef’s clients was in his 70s and wanted to know when he’d be able to go on dates again. She told him honestly that the COVID-19 pandemic had put the brakes on many dates in the older age group, especially with grandparents who interact with unvaccinated children and grandchildren as the Delta variant became more contagious and it affected young children.

“We’re in a situation with family holidays and things coming up. I wanted to express to him that he may be vaccinated, but we’re back to the reality of breakthrough cases,” she said. “Dating isn’t a priority for everyone, but the good news is that since kids five and above are being vaccinated, it’s looking like Christmas will be a new dating season!”

The Stef and the City logo
Stef and the City gives clients a chance to get to know each other before dating in person.

For example, she said that she was initially excited that her daughter started in-person school, but then her daughter had sat next to a child who tested positive for COVID-19. She and the entire class (and many frustrated parents) had 10 hours to make arrangements to quarantine and home-school for two weeks. That’s why she encourages clients not to take a lack of communication so personally.

Years ago, singles could make what seemed like an endless number of connections. But now, some people aren’t as interested in dating. That’s not necessarily a condemnation of another single they met online, but instead could be an indication of their mental health or emotional concerns they have.

“It’s kind of sad that people feel that sense of rejection,” she said. “Maybe they need to take a break from this because it’s not working out. That’s not a horrible thing. You just have to be more patient, and, hopefully, people listen to that.”

Taking it slow can mean more phone conversations, too. It can take time to get to know someone, although that can be challenging for people who feel there’s a timetable in terms of fertility or other reasons.

Stef and the City: Daters Can Push Past Pandemic Fatigue

The COVID-19 pandemic has impacted people differently based on where they live. That’s why Stef recommends her clients spend some time understanding how they are feeling.

“How did it affect us emotionally? People who have had social isolation are feeling it the most,” she said. “Each person’s situation is unique. Even talking to other matchmakers, you see a very different experience.”

Stef is a member of the Matchmaker Alliance Group, with agencies in New York, New Jersey, and the District of Columbia. She said industry professionals have learned to become flexible and creative to help clients find love while staying safe.

For example, she said she had plans to meet a new client who canceled less than an hour before their appointment because he wasn’t feeling well. As it turned out, he tested positive for COVID-19.

“I’m in that situation where everyone is dealing with this in different ways,” Stef said. “Hopefully, people will learn better communication techniques because we don’t have the same option to just go out and meet people.”

Meanwhile, she encourages clients to continue working through the personal issues they want to fix. Stef said she often reminds singles ready to date that no one is in a perfect situation, especially during these challenging times.

“We all have lessons to learn,” she said. “If we didn’t, we would’ve known how this pandemic would go.”