Professional matchmaker reveals how she finds love for her clients

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Anna Leifeste, 28, from Chicago, Illinois, is a full-time matchmaker at Three Day Rule, a personal matchmaking company based in Los Angeles
Three Day Rule has matchmakers in Los Angeles, San Francisco Bay Area, New York City, Chicago, Boston, and Washington, D.C.
The highbrow dating service charges users $3,500 for its best three-month package, and $5,000 for six months

Published: 11:56 EST, 28 September 2015 | Updated: 16:39 EST, 28 September 2015

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A woman who gets paid to take control over other people’s love lives has revealed what it’s really like to work as a professional matchmaker and meddle in the romances of lonely singles across the country.

Anna Leifeste, 28, from Chicago, Illinois, helps her clients navigate the 'roller coaster' world of dating as a full-time matchmaker at for Three Day Rule, a highbrow online dating service headquartered in Los Angeles. And now, in an essay for xoJane, Anna has offered would-be cupids everywhere a glimpse into an average day on the job, which includes a trip to an outdoor concert to scour the crowd for singles who may be the right match for some of her clients.

'At its core, my job is about one of the most heart-warming, meaningful things in life - relationships. Yet, my work is not just warm and fuzzy. It is also strange and challenging,’ she explained.

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Love on the brain: Anna Leifeste (pictured), 28, from Chicago, Illinois, is a professional matchmaker who works at Three Day Rule, a personalized matchmaking company based in Los Angeles

Three Day Rule, which helps its clients navigate the online dating world, charges $3,500 for three months of personal matchmaking and $5,000 for a six-month package that includes date coaching, styling and professional photography, according to Online Personal Watch.

Anna, who has a master's degree in counseling psychology from Northwestern University, said she begins her day at 7am with a walk. And while the purpose of her morning jaunt is to start her day on a 'relaxed note', her mind automatically wonders to a potential match for one of her clients.

During this particular outing she remembered that 'Bob' was excited about an upcoming concert, so he might be a great fit for 'Jane' - who previously worked for a music venue.

These moments (“A match! I really think it could be a match!”) feel like such a high

Anna said she made a mental note to check his religious and political beliefs when she got home because they were ‘deal breakers’ as far as ‘Jane’ was concerned and could potentially mean a quick end to Anna’s romantic plans for the pair.]

But even before investigating ‘Bob’ in greater detail, Anna confessed: 'I’m excited about the possibility of the two of them together.’

After heading home to shower and answer emails, Anna had a 10am 'post-date debrief' with another client and her match.

Anna explained that she typically speaks with the match to see how a date went before she calls her client. And while he had 'very nice things to say' about his date and their night out, he also told Anna that he thought she was 'hard to read' and questioned whether they had 'enough chemistry'.

'Feeling like friends has been the stumbling block in her past relationships and so she (understandably) wants more intrigue and electricity,' she noted of her client. 'Here's the bittersweet news - she felt that electricity on this date!'

On the go: Anna explained that she is constantly meeting potential matches for her clients - and admitted that she even attended a concert in Chicago just so she could scout the crowd for single men and women

According to Anna's client, they had great banter and he 'made her feel wanted', but after listening to her 'giddy feedback', she makes a point to 'temper expectations a bit'.

'I talk with her about opening up more on the date, showing him more of her quirkiness, humor, and interest in him, which will hopefully address his concern of her being "hard to read",’ she explained.

'I also emphasize that, whether things work out with this particular guy or not, it's great that we're on the right track personality-wise,' Anna added.

My flexible, autonomous schedule is a blessing and a curse

At this point, Anna said she headed downtown to have back-to-back meetings with potential matches. Before meeting with the first woman, Anna explained that she already had a prospective date in mind – a man in his late 50s, who heads up ‘several large companies’ but ‘showed up to our meeting in Converse and perfectly mussed hair’, a complete contrast to the corporate figure many women might expect.

However, upon meeting the woman, who wore pearls and talked about gardening for much of the session, Anna quickly came to the realisation that she wouldn’t be the right fit for her dressed down client – who, she added, has a bit of a ‘rock-and-roll streak’.

Instead, Anna said she would refer the woman to a colleague who was working a 'more polished, conventional client'.

Thankfully, Anna’s next meeting proved to be far more successful; one of the men she met that day appeared to be a great fit for one of her female clients, so she explained that would write a 'quick bio' about him and send it to her client along with a photo to get her excited to meet him.

'These moments (“A match! I really think it could be a match!”) feel like such a high,' she said.

In between meetings, Anna spent her time sending emails, returning client calls, writing detailed bios and scheduling more meetings. At 6:30pm Anna had a final meeting with a guy who just joined the Three Day Rule network.

'The meetings are my favorite part of this job, and we pass the time happily chatting as I ask questions to learn about him, his romantic history, and who he's interested in dating,' she explained.

Anna revealed that that while she was recording his answers, she is also writing 'quick impressions of his body language, jokes he cracks, any topics that he talks about with passion, etc'.

Video courtesy of TwoDrunkGirls.net

Works like a charm? Three Day Rule, a highbrow online dating service headquartered in Los Angeles, charges its clients $3,500 for its best three-month package, and $5,000 for six months of matchmaking help

'The whole point of meeting people in person is to get a 3D sense of them and really understand the intangibles that online profiles just can't express,' she noted.

After a full day of work, Anna met up with a fellow Chicago-based matchmaker named Heather. The two headed to Millennium Park to attend an outdoor concert. However, far from being a fun jaunt between friends, the event was actually all business, as they were there to scout the crowd for matches for their clients.

On the way they there, Anna and Heather came up with a list of the age ranges, genders, and physical types that they are looking for.

'At the event, we're constantly moving,' she explained. 'Hovering near the entrance and casually approaching whoever seems like a good potential, then making our way to the line for beers, where it's easy to chat with the other people in line (you better bet, we choose our moment to get in line based on the cute group of late-30s men who are clearly not on dates!).'

According to Anna, they will sometimes come right out and say they are professional matchmakers and other times they will find a way to work what they do into the conversation.

'One woman is the exact type we're looking for - that's the weird thing about approaching people in person,' she said. 'It's the total opposite of online where you know all of their stats up front. All I know about her is her general vibe - her appearance, style, energy, body language, and way of interacting, but I already have the sense that she could be an amazing fit for one of two clients we're working with'.

At the end of her essay, Anna explained that the following day will be completely different, although she will do many of the same things.

'My flexible, autonomous schedule is a blessing and a curse,' she noted. 'I get to make my own routines (like my morning walk), but there's also no firm boundary between my time and work time.'