I didn't use AI to write this essay - so please forgive its rambling quality. For a condensed version please copy and paste this into your AI chat bot.

Ahem.

I started A Good First Date Matchmaking on May 21, 2026 by posting a simple ad on my Instagram page. The idea was simple: meet me for 30 minutes and I will match you for free. If you like your match and feel good about the experience, you can make a contribution. But you don't have to. No guarantees.

The response was overwhelming. Within hours of posting, I had my first emails requesting a 30 minute in person interview in Tribeca. This is significant because a) it is annoying to email somebody - I specifically did not have a sign up link because I wanted people to make the effort, b) I did not offer free reschedules - so while it was free to meet me, reschedules would be $100 and c) the meetings would be in Tribeca which is convenient for me but very out of the way for a lot of people.  

These built in filters helped me weed out people who weren't serious. They also helped attract people who were naturally curious, open minded and above all, really wanted to find love and were willing to do the work, including meeting with a total stranger to talk about their love life.

In the weeks that followed 80 people made appointments. Two canceled last minute - one due to a meeting, one because of a dog.  One person was 20 minutes late due to traffic. And one person requested a reschedule 45 minutes before the start of the appointment offering to pay the $100. I declined her request because I didn't want to work with somebody who might treat my client in the same way.

The rest of the responders, 76 clients in all, showed up on time and ready to sign onto the program. They sat with me one on one, shared their stories with me, allowed me to take a short video of them and signed an accountability contract, vowing to treat every single person with respect, vowing to be responsive and my personal favorite: they took the vow of no ghosting.

A Good First Date Matchmaking (AGFDMM) is a program I'd had in the back of my mind since I had my first experience working as a matchmaker in 2017. Without going into detail, I've always loved matchmaking but hated working on a timeline, especially with thousands of dollars at stake. When I had to make three matches in three months, I was constantly under pressure to slam two people together just to fulfill the terms of the contract. Which is why I only lasted a couple of months as professional matchmaker and why I ultimately became a dating coach in 2018.

As a dating coach, I helped people revamp their profile and work on texting, communicating and dating. The idea behind my work was helping people become their own matchmaker. And for a while the work I did was very rewarding and effective. But over the past couple of years I noticed a shift. It felt like people weren't giving each other a chance. For my conventionally attractive clients, they were getting too many matches with people that didn't have any intention of following through. For my less conventionally attractive people, they weren't getting any airtime at all.

I always thought, if I could only explain why this person is so great, I'm sure more people would want to date them. I thought of people like my mom (who passed away) - I always wondered how she would meet people if she was single. Or friends who weren't models and were scared to get back out there. How could I help them have a good experience?

The best way to help was to become a matchmaker myself but instead of charging big bucks and unrealistic timelines, I would offer my services for free. With the hope and belief that, if I brought two people together, they would eventually pay me. Or not. I just didn't know what would happen.

***

It's June 17th today, roughly one month since I began this journey. The program has shifted and changed over the past few weeks as I continue to learn about the best way to bring people together.

The first thing I had to think about was the imbalance between men and women in my dating pool.  It was extremely unbalanced as I expected.  So instead of waiting around for a bunch of guys to sign up, I decided to use my client base to grow and expand the network. Bumble has millions of users, I had 76. The only way I was going to scale would be through leveraging this network.

The idea was called the Matchmaker's Match (MMM). This would be two clients, women, who were roughly tangential to each other. By bringing them together and having them share their stories and who they were looking for, now I had an additional pair of eyes and ears on the ground to help me.

So often girl friends tell each other things like, "Oh I know this guy I will totally introduce you." But then they forget. Or they connect you but the guy doesn't follow through. Or worse, the date happens but there is zero connection and you're left wondering why your friend hates you so much.

The MMM was designed to formalize this process. If you see something say something - if after your MMM meeting you see a person, man or woman, that reminds you of the other person, send them to Grace and I will process them and match them accordingly. This way, the two clients wouldn't have to worry about age, height, appearance, etc. I would do that for them, I just needed the referrals.

The second idea was that, in the absence of providing a love match, I wanted to help introduce women to each other that had a connection. I had one client who said that she wanted a partner who thought her "dumb idea" to create products for the airport would be interesting and fun. I had another client who had successfully launched several products like that. They just fit. Another pair didn't have that much in common except that they were extremely quirky in the same way. During my initial intake interview with each of them, they continued to surprise me in the same way.

As I sat and observed these MMM meetings I came closer to an idea: I want to introduce you to your best friend. Whether this is your soulmate or your best girlfriend. The idea behind A Good First Date Matchmaking is to bring likeminded people together. If I find the love of your life, GREAT! But if not, then I want my clients to have fun and learn and grow along the way.

***

Now at a month in I'm still grappling with how to quantify the experiences I've created. I've been thinking a lot about the loneliness epidemic and how my contribution is helping to chip away at this problem. 

In the past month, I've generated over 100 hours of in person human interaction - whether that be via meeting clients in person, putting clients together and of course, actual dates.

Some people ask, how do you expect to make money doing this? The answer is: I don't. I don't think that money and love belong together. Instead, I hope to eventually turn this project into a non-profit and to raise money from foundations and government agencies that have made combatting loneliness their mission.

***

Well, that's about all I have to say right now. I have much more to say, but at the risk of not publishing this at all, I will just go ahead and launch this unedited train of thought.

Happy to answer any questions!