These Old School Matchmakers Help Clients Overwhelmed with Dating Find Love

— -- Two women attending a networking mixer in Chicago slowly made their way around the room, whispering to each other and pointing out different people they thought were attractive.

“So like over here, there’s a tall guy in the back,” said Heather Norman, gesturing.

Her partner in crime, Anna Leifeste, went up to another man and asked if he was single.

But these ladies weren't looking for themselves. They are professional matchmakers who get paid thousands of dollars to find matches for their clients.

“We spotted a couple of good people in the corner,” Leifeste said. “We have two clients in mind so we’re going to head over this way.”

In a world full with dating sites and apps, old school matchmakers like Leifeste are able to make matchmaking a full-time career by doing all the ground work for their clients.

“One thing clients love is that they can have a long day at work and decide that they don’t want to go out to that event. They know that we’re out there working for them,” Leifeste said.

Leifeste works for the national matchmaking company Three Day Rule, jokingly named after the bad dating advice line from the movie “Swingers.”

When she sits down with a new client, Leifeste will go over the client’s relationship history, profile and dating desires. She said one of the most common problems she sees with her clients who have not been successful finding someone on their own is not having enough time to navigate today’s dating environment.

“We work with a lot of people who are exhausted by the search,” she said. “They might have a really demanding job and so it’s a lot to add dating as a full-time job on top of that.”

Her matchmaking services cost $3,500 for three months or up to $5,000 for six months. Leifeste said her clients never come across as desperate.

“We do not promise deadlines,” she said. “The people that we’re working with have normal lives…these full busy lives that they're happy with and it’s just this one missing piece.”

She goes on the hunt for eligible bachelors and bachelorettes all over Chicago. She and her colleague Heather Norman only take on eight new paying clients a month to focus on their specific needs.

Kelly Barrett, one of Leifeste’s clients, is in her early 40s and signed a six-month contact, which includes a professional photo shoot and six introductions to dates that have been vetted for compatibility.

“I had a birthday last summer and had a couple of dear friends of mine get married and I decided I’m tired of going to these by myself,” Barrett said. “[I] decided that it was time to maybe change up how I was going about my search for Mr. Right -- Mr. Right for me.”

For Barrett, the price was worth it – she's gone on two dates so far.

“I thought that investing in something a little bit more serious would be a good investment,” she said.

In addition to the paid service, Three Day Rule also offers a free database for singles to join as potential matches for paying clients. Those singles won’t be guaranteed any dates, but the matchmakers can reach out if a client is interested.

Leifeste, who is in a long-term relationship, came to matchmaking with a master’s degree in counseling psychology and said there are parts of being a therapist and a matchmaker that are similar.

“It’s a lot about empathy and trying to understand someone else’s point of view and where they’re coming from,” she said. “You just have your clients’ best interest at heart and you know that they’re doing their best and you’re going to do your best for them.”