I’m A Professional Matchmaker—Welcome To A Week In My Life

Monday

We start each morning by going through our active client list and making sure everyone is taken care of: They should all either have a date on the calendar, or one in the works! We check in with all our recent clients at least once per week, even if they are travelling or now in an exclusive relationship.

I try to make a fair price for each client based on a variety of factors that can impact the difficulty of matching, such as how many times they’ve been married, whether they want children, or if they’re looking to date someone a lot younger. Though sometimes I can convince them to take a chance on someone they wouldn’t normally. For instance, there was a couple I set up where the woman had a young son and the man I was matching her with said he was definitely not up for that. But I convinced him to give the date a try, and now they have been married a year. He’s an amazing stepfather, and they are starting their own family!

For lunch, my whole team field trips over to a new vegetarian restaurant, for a taste test. We often contact owners for tastings like this to see if we want to add their restaurants to our date venue list. The restaurant's fresh juices were to-die-for, so we decide to send several couples there in the coming weeks.

Back at the office we conduct interviews of potential dates for our clients. We were at a housewarming party for one of our female network members last week and met tons of her close girlfriends, and now they’ve booked up the rest of our afternoon! Referrals from our network mean more date options for our clients, so we love when this happens. We know we like these women, since we met them in person, but now we need to screen them with a comprehensive 75-question questionnaire and an informal energy reading.

Energy reading, to us, means finding that je ne sais quoi in each candidate. It can be the way they laugh, the way they sit, their mannerisms and gestures…and then seeing how those things line up with another match. We use the questions as guidelines, and try to have an organic conversation about their relationship history and goals, while noting everything down for their “accounts.” We often go off on tangents chatting about careers, current events, or recent vacation spots, which is great because it gives us a better sense of how these candidates socialise and helps us to properly match them. In the evening I head to SoulCycle, my favourite fitness class. There’s always an amazing group energy, so you often end up chatting with your bike neighbours afterwards—and you can be sure that if they are single and attractive, they will walk away with one of my business cards! Today I meet a cute investment banker and a glamorous model-turned-nutritionist.

Tuesday

This morning we’re decorating! We recently moved to a new office because we needed more space, and today we received a shipment of furniture. Our team gets to work installing the simple pieces. We’re also creating a “Wall of Weddings” showcasing photos of successful couples we have introduced over the three years we’ve been in business. During that time, we’ve matched close to 100 couples! It’s been a bit sentimental reminiscing on those introductions and first dates.

Later on, I meet with a prospective client at La Pecora Bianca, my go-to for iced coffee or a dangerously strong Italian espresso. I want to see if he is a “match” for our company based on his look and energy. I learn about his tastes and preferences, and we chat candidly about his divorce and what didn’t work in his first marriage. I love that I get to have such a meaningful conversation with someone I’ve just met. Being a professional matchmaker somehow makes people open up to me much faster, which is absolutely fascinating, and my favourite part of the job.

I take a beauty break and just make time for my blowout! (I am terrible at doing my own hair, and tonight we have a special soiree) While the stylist works magic, I catch up on emails. At the party later, my team and I are introduced to SO MANY potential date candidates. We invite them into the office for guest membership interviews next week. Candidates come in many forms, but they all need to have a strong desire to be in a committed romantic relationship. And my team has to genuinely like them all; if I don’t like them as people, I can’t introduce them to my network and maintain the respect and loyalty of my other clients.

Wednesday

After a workout and a morning coffee run, I head into the office for a busy morning interviewing potential employees. I currently have five people on my team, and two of them went to a networking event last week to recruit summer interns and a new assistant. We’ve been flooded with resumes and some really thoughtful and specific cover letters, too! To expedite the hiring process, I’m interviewing the best candidates through FaceTime calls, which consume my entire AM.

My team orders lunch together every Wednesday. It’s a good opportunity to all close our laptops and turn the “work” off for an hour, though we often end up talking about matchmaking anyway because it’s juicy and we love it! Afterward, I spend the rest of the workday shuffling around my Polaroid photos of each club member, trying to get next week’s matches just right. The Polaroids are a great visual tool to help me keep all the people I meet (there are more than 2,000 in the current network!) straight in my mind.

Tonight I’m swinging by a few of our favourite restaurants for meetings with the owners and general managers. We need to make sure that not only are the first date reservations handled, but also that our clients are provided VIP treatment and a special touch to each date. To ensure this, we have to do a little wining and dining ourselves and remain friendly with the people in charge.

Thursday

I am up early this morning for an hour meditation session. It helps me focus the rest of the day, and I find it to be restorative. The session’s just what I need before checking in with one of my clients who is experiencing what I call “candy store syndrome.” He has liked all of his matches, but hasn’t gotten past a few dates with any one of them, because he’s then so excited about who might be next! I remind him that the company is called LastFirst because our mission is to send him on his LAST first date.

We look back over his date log to discuss positive and negative qualities in each match, and I take some notes. We realise that the first woman he met through us may actually be “the one that got away,” so I later call her to casually get her thoughts on seeing him again. She hears me out and says she’s open to seeing my client again!

Tonight’s my date night. My fiancé, Ross, picks me up from the office and together we walk to our favourite neighborhood restaurant. We talk about our upcoming trip to California and play some footsie under the table. A bottle of wine later, we’re practically falling asleep at the table from our busy days. We order double espressos so that we can potentially watch the new episode of Fargo when we get home.

Friday

My day starts with a sweat session at SoulCycle, then I hit the road with Ross for a weekend in East Hampton. We have a little house there and it’s the perfect spot to set up a matchmaking Summer Camp, since so many of my clients are out that way for the season, plus it’s a fantastic singles scene. I give my team the option every Friday in the summer to either work from the office, or Jitney out for the day to work with me poolside (or fireside, in today’s chilly case)! Usually they pick the latter, but today I’m on my own.

My team has stacked up my afternoon with client phone calls, mainly for collecting post-date feedback since we had five couples out on first dates last night. I stroll around the neighbourhood for the first few. Mainly I just listen on these calls because I don’t like to be too aggressive with my coaching. Sometimes I suggest a light “tweak,” like if I hear that someone wore a silly outfit or told a tasteless joke on the date. The post-date feedback calls are really helpful for us to learn more about our clients and guest members’ preferences and dating styles, as we continue to zero in on The One for each of them. On the fourth call, my client is so excited about his date last night that I rush back to my laptop to type notes as he speaks. I call his date up next, and it was a match on her end as well! Now I’m emailing him a list of cool “non-dinner” second date ideas—trapeze class and pizza making among them!

We finish every Friday with an end-of-week report, presented to me by a different member of my team each time. I FaceTime into the office for this, and my Projects Manager Rachel talks me through our accomplishments of the week, as well as our goals for next week. I’m thrilled with the week we’ve had, but more than ready to get my weekend started!