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Stef and the City


Owner Stef Safran is “Chicago’s Introductionista®.” With over fourteen years experience in the professional dating services industry, and as a professional matchmaker in Chicago, she takes pride in successfully matching Chicago’s single men and women. As a professional introduction service and premier dating agency, Stef and the City offers personalized matchmaking and dating coaching services. Whether you are dating singles over 40, just out a few years out of college, ready to date after a breakup, or looking for someone who shares other specific qualities, you have come to the right place!

With our personal introduction service you get information that you are NOT getting from your friend’s fix-ups or the online dating sites!

Our introductions include:

  • Each person fills out a detailed questionnaire and meets with the Stef and the City staff!
  • Structured expectations on how to date
  • Getting asked out on a PROPER date!
  • Personalized service: speak one-on-one to a person,
    about you are looking for, not to a computer or machine!
  • Understanding your dating history: Looking into your past relationships and your physical type.
  • Important feedback: We give feedback to understand how the dates are going so you are not left in the dark!
  • There are no promises of people that do not exist!
  • No more wasting time: guaranteed introductions!

Most Internet dating sites charge at least $35.00 a month- and that doesn’t guarantee a single date!

Ladies, our prices can start at just $50.00* for a basic introduction- that’s less than most people are spending  just to go out and meet someone on their own, so what do you have to lose? Your time is valuable and you need a company that gets it!

Read testimonials from our matchmaking clients!

Regular Matchmaking Services: Men

We know your time is valuable.
We know you want to meet attractive, quality singles.
We know you want options.
We know you don’t want to waste time on bad dates.
We know you want to be excited about who you get set up with.
We know you want us to do the work!
We have contracts that allow for you to be flexible and make time for actual dating.

Regular Matchmaking Services- Women

Ladies, we know you want to meet quality men.
We know you are looking for men who know how to date.
We know you want to be asked out.
We know you want commit minded men.
We know you love follow through.
We know you want someone else to help you in this process.
We want to help you in the process.
We want you to enjoy dating again!
We want you to fall in love.
We want to help you find the happily ever after!
We will be honest with you about what you can expect.
We have a pay-as-you-go program for women, so you can afford it and can feel that we listen to what YOU want.

*Prices vary by age and specifications

Michael, age 27
“Stef introduced herself to me at a networking event. I told her if I met someone I would send her tons of referrals. Sure enough, my 1st date she set me up with lasted 8 hours and resulted in a woman I happily in a relationship with for the past two years. I have sent Stef many referrals since then!”

"Read more testimonials from Matchmaking clients"