The Strange and Challenging Reality of Being A Full-Time Professional Matchmaker

Dating is a roller coaster and, as a professional matchmaker, my job is to go on that roller coaster for each and every one of my clients.
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Anna Leifeste
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Dating is a roller coaster and, as a professional matchmaker, my job is to go on that roller coaster for each and every one of my clients.
 Anna Leifeste in Chicago

 Anna Leifeste in Chicago

​If you asked a dozen matchmakers what their job is like, you would get a dozen answers. Dating is a roller coaster and, as a professional matchmaker for Three Day Rule, my full-time job is to go on that roller coaster for each and every one of my 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.

To get a better sense, let me walk you through my day yesterday:

7:00am 

I head out on morning walk -- my time to listen to podcasts and start the day on a relaxed note. This is not supposed to be work time, but I constantly have work-related thoughts on my mind. A lightbulb goes off about a potential match for a client: “Oh! What about “Bob” for “Jane”? I just remembered that he was nerding out about an upcoming concert when we met and she used to work for a huge music venue. 

Note to self: Check on his stance on religion and politics (her dealbreakers) as soon as I get home. I’m excited about the possibility of the two of them together.

​8:30am 

I'm showered, caffeinated and in front of my computer to answer emails. It's a healthy mix of check-ins with clients and matches, scheduling upcoming appointments, and marketing projects. While Three Day Rule has a dedicated business and marketing team in California, my local colleagues and I love getting involved in all of the Chicago-specific press and events.

10:00am 

I have calls with a client and a match who went out for the first time last night. One of the most valuable parts of working with a matchmaker is the detailed post-date debrief. You know how frustrating it is to never get answers on why things don't go to a second date? Or why that person decided to ghost you? Our matchmaking process allows you to learn any useful information about what's working on dates and (more importantly) what isn't working.

I speak with the match first and he has very nice things to say about the date and the woman he met. He’s open to seeing her again but tells me that he found her "hard to read" and he is not sure if there was enough chemistry. 

This information is helpful going into my next call, which is with my client. We have been on the hunt for a guy who is not only smart, established, professional, and kind, but also very playful and flirtatious. Feeling like friends has been the stumbling block in her past relationships and so she (understandably) wants more intrigue and electricity. Here's the bittersweet news -- she felt that electricity on this date! 

He bantered and teased her and made her feel wanted. As I'm hearing her giddy feedback, it is so helpful to already know what he's thinking. I'm able to show my excitement, but also 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."

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. When we first met a few months ago, she didn't know she needed playfulness and flirtation, so we end the call in agreement that it's fantastic progress to have honed in on this quality she needs in her matches.

11:00am

I'm downtown for several back-to-back meetings. The first is with a woman I'm hoping will be a match for one of my most charming, charismatic clients -- a man in his late 50s who runs several large companies but who showed up to our meeting in Converse and perfectly mussed hair. 

When we first met, he talked happily about his grown children and the companies he has built, but what made him light up was recounting his messy stint in his 20s when he lived in New York City and tried to make it as a musician. It is so clear that he needs a match who, while mature and self-assured, also has a rock-and-roll streak. 

The woman I'm meeting with shows up wearing pearls and talks a lot about gardening. She is lovely, but won’t work as a match for the client I had in mind. 

I do spend 45 minutes learning all about her and her preferences in dating, and make a mental note to touch base with my colleague who is working with a much more polished, conventional client around the same age. She could be a great match for him.

I sneak in snacks and coffees between the next three meetings. One potential match for another female client is exactly who I hoped he would be. Tonight, I'll write a quick bio about him and send it to my client along with his photo. Hopefully, they will be making plans for drinks by the end of this week. These moments (“A match! I really think it could be a match!”) feel like such a high.

My next meeting is with someone who wants to be a client. She was referred by a friend who is having a great experience working with one of my colleagues in LA. I spend time really trying to get to know her. “What makes you laugh? Do you know your love language? When you say you're religious, how is that a part of your life? What would your exes say it's like to date you?” 

I answer her questions about what it would be like to work together, how our process works, and where I think I'd find "her guy"... We agree that he, like her, is too busy to attend networking events. I imagine I'm more likely to bump into him on the lakefront path doing something active, at a charity event catering to professionals, or possibly at a live sporting event -- so those are the places I'll be spending my time while working with her.

4:00 pm 

I have a gap in meetings, which feels necessary since my emails have piled back up. A few responses to matches I sent out yesterday have come in. A couple are quick acceptances (the best!), so I exchange contact information.

I then meet another Chicago matchmaker, Heather, to coordinate on our top matching priorities. We sit side-by-side at a cafe with our laptops open, running through a list of items we need to discuss. 

For example, we each met a potential match for the same client, and since they both look good on paper, it’s time to discuss the intangibles and impressions from our meetings to decide who the client would like best. 

The woman who emphasized her independent/competitive streak wins out -- the client we're matching loves to compete and values directness and self-sufficiency in his partners.

5:30pm 

I'm inhaling a Thai salad for dinner while returning client calls. They include doling out advice about how to approach a second date and another feedback session about what sparked on the first date and what didn't. 

I also write a couple of detailed bios, based on the notes I've taken in recent meetings, and send information on potential matches to my clients. It's important to give people thorough information about who they're going to meet (including photos) to make sure they're excited to go on the date!

6:30pm 

I fit in one more meeting, this time with a guy who joined our network and was interested in meeting, even though I don't have a particular match in mind for him right now. 

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. 

Along with taking notes on his answers, I am sure to jot down quick impressions of his body language, jokes he cracks, any topics that he talks about with passion, etc. 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.

7:30pm 

I meet back up with Heather and we walk over to Millennium Park to catch the last outdoor concert of the summer. Unlike everyone else, we aren't just there to enjoy a picnic and some music. Instead, we are scouting for great matches for our clients. 

On the walk over, we run through a quick list of who we're looking out for -- an event this big and widely-appealing will have all types of people, so our list of who we're looking for is long. We discuss general age ranges, genders, physical types, and attitude/vibes that we're prioritizing. 

At the event, we're constantly moving. 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!).

Depending on the person and situation, sometimes we come right out and ask if they're single and explain that we're matchmakers. Other times we let conversation develop organically, and when it inevitably turns to occupation or what we're doing at the event, we find an opening to explain Three Day Rule and the work we do.

By the end of the event, Heather and I each have a handful of people we will follow up with tomorrow to set up times to meet for coffee. Other people we've met are in relationships, but just might send their eligible single friends our way. 

One woman is the exact type we're looking for -- that's the weird thing about approaching people in person. 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. 

It's just like when you sit down on a date and know within 3 minutes if you're intrigued or not. I can't wait to sit down with her over coffee and learn the details to see who she could fit well with!

Tomorrow will be a radically different day, with many of the same pieces rearranged. My flexible, autonomous schedule is a blessing and a curse. I get to make my own routines (like my morning walk), but there's also no firm boundary between my time and work time. 

Plus, there's nothing more motivating than the feeling that you're responsible for the relationships of people you care about. This makes it hard to take breaks, keep a normal schedule, and be out in the world without constantly scouting and wondering if you should approach people. It also makes me stay focused, energized, and hungry for the next great match.