Stef and the City™ Helps Busy Professionals in Chicago Find Love With Hands-On Matchmaking & Dating Coaching

The Short Version: A big city like Chicago might seem like it’s teeming with singles, but some find the abundance of choices overwhelming. For those who are new in town or too busy to date on their own, matchmakers offer a shortcut to love. Based in Chicago, Stef and the City is a matchmaking firm with a database of screened dates ready to go. The Founder, Stef Safran, is a dating coach and matchmaker who emboldens singles to expand their social calendar and take advantage of opportunities to meet new people. She understands time is a precious commodity for singles, so she’s happy to point her clients toward vetted dates, popular events, and even travel packages to expedite romance.

Jennifer, a single girl in her mid-20s, couldn’t help but vent to her friends over lunch one day. She’d been living in Chicago her whole life and felt she’d exhausted her dating options. Frustration obvious in her voice, she talked about how hard it was to meet a quality guy in the city.

Lucky for Jennifer, a matchmaker and dating coach was sitting nearby and listening intently. Stef Safran, Founder of Stef and the City, overheard the dilemma and knew she could help, so she took action. She gave the young single her card right there in the middle of the cafe. With raised eyebrows, Jennifer took it.

Stef Safran established her own matchmaking firm to give singles hands-on assistance.

Three months later, Jennifer was ready to give matchmaking a shot and scheduled a one-on-one consultation with Stef. “I was concerned that anyone she might find would be a lot older than me,” Jennifer remembered, “but Stef told me she would take my criteria seriously.”

Stef lined up a date for Jennifer (they were the same age), and the couple hit it off, talking for eight hours. They ended up in a long-term relationship, and Stef was thrilled to witness their blossoming romance.

She told us, “Jennifer had that life-changing experience all because of a flippant comment she made to a friend.” And, of course, because of Stef’s talent at pairing people up.

As a matchmaker and dating coach, Stef frequently saves Chicagoans the time and effort of finding a date on their own. From putting together a personalized social calendar to recommending thoroughly vetted first dates, the team at Stef and the City can get singles out of their rut and into a quality relationship in no time.

“I like working with people,” Stef said. “With matchmaking, it’s really great when you know you connect two people who would never have met without you.”

When Stef started helping singles, pagers were still a major form of social communication. She worked as a contest coordinator for “The Dating Game,” a game show where bachelors and bachelorettes searched for a potential date.

Stef got her start recruiting singles for a game show in L.A.

As part of her job, Stef was networking with many good-looking singles in Los Angeles to recruit people to appear on the show. A top Chicago matchmaker then tapped Stef to recruit singles for a private matchmaking firm. Eventually, Stef decided to branch out and start her own firm, Stef and the City, to focus matchmaking and dating coaching services around the client’s social life.

Today, as a matchmaker, she applies her networking skills to her job by collaborating with other matchmakers around the world. Through partnerships and good relations, she sees to it that singles can find help no matter where they live.

“I fell into matchmaking,” she told us. “I used the skills I learned in business school to grow the company, and as I grew, I started getting in touch with people, gaining colleagues, and honing my brand.”

Stef and the City clients range in age from 24 to 50 (sometimes older) and are typically white-collar professionals. These people are college-educated and often too busy to search all over Chicago for that special someone.

Romance takes time to find, and a matchmaker can put in the hours to narrow down anyone’s search for love. From one-on-one consultations to giving feedback after a date, Stef is there to assist and support her clients every step of the way.

“I am completely hands-on,” she said. “I do all the matchmaking. Every client, guy or girl, meets with me and works with me personally.”

Stef and the City gives clients a questionnaire on personal details including eye color and occupation.

As a first step, Stef gauges the personality of her clients by sitting down and talking with them about their dating history and life goals. She listens closely to get a true sense of who that person is and what their priorities are in life. She takes on no more than 20 clients at a time so she can offer personalized attention to each individual.

“I thought I might be a hard type to match up,” said Rebecca, a former client, in a testimonial, “but Stef assured me that she would keep her eyes out for me. Three months later, she introduced me to Tom, and it was an instant connection!”

Stef’s motto is “Revitalize your social life” because she takes a comprehensive approach to increase the opportunity for dating in her clients’ everyday lives. She coaches singles to network at events, join clubs, and generally become more social and active as a way to meet new people.

She often advises her clients about the best dating techniques, but she also offers more nuanced services to improve the dating experience for her clients. Her coaching style is action-oriented, meaning she creates a concrete plan for her clients to follow during a six-month period. Stef and the City has a two-pronged approach, helping facilitate in-person socializing at events as well as online flirting on popular dating websites.

“After Stef and I set up a plan, I ended up dating four different guys and (was) able to choose who I wanted to be with,” said Amber, a 32-year-old client who ended her dating dry spell with Stef’s help.

1. Social Calendar: Proactively Planning Ways to Meet People

Stef and the City jolts singles out of their same old routine and pushes them to become more social. A team of dating experts can craft a personalized social calendar for clients to jump-start their dating life. This service strategically plans out how you spend your time, suggesting charity events, classes, gyms, sports leagues, networking opportunities, and other singles events in Chicago.

“Stef was able to help me establish what places I should go to meet people my own age as well as ways to establish myself professionally,” said Sam, who was new to the city and so enlisted Stef’s help to meet people. “I would definitely recommend trying a social calendar through her.”

2. Online Dating Profile Help: Marketing Your Strengths Online

Some singles want to conduct their own search for dates, but need a little help making sure they’re putting their best foot forward. Stef can coach these singles on how to write a profile or message when online dating.

“After Stef and I set up a plan, I ended up dating four different guys and (was) able to choose who I wanted to be with.” — Amber, one of Stef’s dating coaching clients

Stef and the City’s team of writers, stylists, photographers, and dating experts can help you market yourself on a dating site to maximize the number of replies you get and save you valuable time.

Stef and the City are open to all routes to love. That’s why they offer an array of services and recommendations to clients. The team understands that meeting people can be a challenge, so they provide easy access to resources to get started.

On Stef and the City’s website, you can find local opportunities for singles travel and singles events listed to help people get active. From weekend getaways to evening wine tastings, these social activities are full of fun and romance.

Watch on

As an added benefit, Stef partners with companies that foster date opportunities for singles. Her website offers valuable discounts on single travel packages and local events to make socializing more affordable. “After age 30, it can get really difficult for people to make new friends,” she said. “So, there was really a need for more ways to meet people in Chicago and cut to the chase.”

Stef encourages singles to be proactive and never lose hope. Whether you’re new to Chicago and looking for social connections or a lifelong Chicagoan, like Jennifer, who just needs a shortcut to finding the right person, Stef has decades of experience working with singles.

Through social calendars, online profile management, and matchmaking services, Stef and the City gives clients the chance to mingle in a variety of ways. Stef takes an active interest in helping singles brush up their dating skills and connecting her clients to lasting relationships.

“The whole process is definitely about self-discovery and understanding your boundaries,” Stef said. “Sometimes for people, it’s just about getting back out there and feeling recharged about dating.”